Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine. 

Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows! 

As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor.

This is The Real Portland Tour!

Check my website for a complete listing of tour days, times, and availability. 


The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailors for centuries, each offering a chance to delve into their rich history. While most lighthouses aren’t open for tours, you’ll still get up-close views and plenty of opportunities to admire their stunning architecture and scenic surroundings. As you navigate through Portland’s picturesque coastline, you’ll be surrounded by breathtaking views that are as storied as they are beautiful. This focused, relaxed tour is the perfect way to connect with maritime past while soaking in the charm of Maine’s coastal landscape.

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour 

This 50-minute sightseeing tour is a fun and unique way to discover Portland, Maine. Board a Vintage Fire Engine and travel back in time as your knowledgeable guide helps relive Portland’s colorful history from a local’s perspective. See lighthouses, Civil War forts, city parks and buildings, interesting stories and a multimedia experience packed with historic images of Maine. This is one family-friendly tour you should not miss out on!

Vintage Fire Truck Sightseeing Tour of Portland Maine

The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland peninsula. Towards the end of the tour, we make a 20-30 minute stop out at Portland Head Light in Cape Elizabeth. 

Discover Portland City and Lighthouse Tour

Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that guide mariners into Portland Harbor.

Harbor Lights and Sights Cruise

Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising stories largely left out of the history books. Get ready to broaden your sense of what Portland and Maine have been and could be.

Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, we'll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. We’ll see where Indigenous Wabanaki leaders made their earliest relationships with European colonizers and walk together through the centuries.

Enjoy an inclusive, empowering, and surprising constellation of tales that offers a welcome contrast to the more obvious themes you’re likely to experience on other tours. You'll enjoy 2 hours of narration over a 1.5-mile route with owner and guide, Dugan Murphy. He is Portland's top-rated guide on TripAdvisor!

Portland, Maine: Hidden Histories Guided Walking Tour

Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commercial Street and continues for 2 hours through the historic Old Port, downtown and waterfront areas, sharing highlights of Portland's history since 1632. 

Some of the locations we may feature on your tour include; the lobster statue, the home of Henry Wadsworth-Longfellow and his place of worship, the Eastern Cemetery, the Abyssinian Church, the U.S. Customs House and more. 

***Tour duration is two "ish" hours, based on guest engagement and pace of the group. Planning on 2.5 hours for arriving early to check-in and make it back to your vehicle post tour is recommended. 

A Walk Through Time Tour in Portland

- Portland's culinary culture is made up of many kinds of artisan food and beverage entrepreneurs from bakers, brewers and chefs to confectioners and more - wherever taste and creativity meet!
- We combine a unique combination of social history, culinary education, the stories of talented entrepreneurs and current award-winning food scene narrated by friendly and engaging local guides
- This tour visits 4-5 venues where you will enjoy a mix of Maine/Maine-inspired cultural, up-and-coming, and trending fare, plenty for lunch with a sweet treat to cap it off.


Old Port Culinary Walking Tour from Portland

A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many as four lighthouses can be seen including a close up view of Portland Head Light, Maine’s oldest and most photographed lighthouse. 

Port City Lights Cruise

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.

Portland Tall Ship Cruise on Casco Bay

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds 

(NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). 

Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Portland, Maine is known for its culinary scene, including amazing donuts. With this tour, you'll get to sample from the city's best donut shops, while also learning of Maine's connection to the invention of the donut and the city's history. Your tour guide will take you not only to the most famous of them all, The Holy Donut, to skip the line, but also to local favorites, that are equally delicious.

Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

Learn about Maine's most famous crustacean and the men and women who make their living from trap to table. Stroll along Portland's vital working waterfront , view lobster boats often unloading their catch and visit Old Port and waterfront district destinations for a progressive, iconic Maine lunch. 

- This walking tour is appx. 1 - 1.5 miles visiting local favorites with plenty of food, and food for thought - lots of time for Q/A. 
- There's always a whole lobster roll, a New England clam or seafood chowder, local craft beer (or soda) plus a whoopie pie or other Maine sweet, and a surprise seafood taste or two along the way. This is our most “classic heritage” Maine experience with a bit of modern flare.

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine coast, lighthouses, and Portland’s history. We have made some modifications to the 5 Lighthouse tour in response to COVID-19. We have modified the tour to allow us not to have guests in our vehicles. As a result of this change, guests will begin biking from the Ocean Gateway and return to the Ocean Gateway by bicycle.  Groups will generally see only 4 lighthouses (Bug Light, Spring Point, Portland Head Light, and Ram Island Ledge). Lunch will be provided by the award-winning "Bite into Maine" Food Truck

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

Trace the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality. Maine’s earliest settlements couldn’t have existed without Black labor, skill, and insight. You'll meet the Black Yankees who founded Maine communities, overturned slavery statewide, drove our maritime industries, gained political influence, crossed color boundaries, and expanded Mainers’ rights in the modern era.

Stepping on granite cobblestones crooked with age — that once saw footfalls from national heroes like Frederick Douglass — you’ll pass storefronts once home to Black-owned barbershops where abolitionists whispered intelligence to Underground Railroad conductors.

Enjoy 2 hours of entertaining and enlightening historical narration over a 1.5-mile route. Owner and guide, Dugan Murphy, dug through the archives to present an amazing constellation of stories left out of most tours. TripAdvisor named him Portland's #1 guide!

Portland, Maine: Black History Guided Walking Tour

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. 

(NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). 

All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Sunset Windjammer Cruise Along the Coast of Portland Maine

This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the bay at dusk. Enjoy evening breezes and city lights on this fully narrated tour of Casco Bay. A great way to end a hectic day or begin a romantic evening!

Sunset Lighthouse Cruise Tour from Casco Bay

Our 3-Hour tour leaves at 11:00 am and follows the scenic South Portland Greenbelt Pathway to three local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble. Next, the tour will pass by Willard Beach before arriving at the final stop, the famous Portland Head Light located at Fort Williams Park in Cape Elizabeth. It is recommended that patrons bring a lunch or we can assist in purchasing lunch from a local food truck that serves Lobster Rolls.

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay. Keep your eyes open for potential seal sightings, as well as the multiple lighthouses, islands, and forts you will see while cruising around.

We will turn the bow toward Portland so you can take in a Maine sunset from the water and then cruise through Portland Harbor as the city’s nighttime skyline illuminates. You won’t find a more spectacular experience in Maine!

GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise through the islands of Casco Bay, passing four iconic lighthouses, historic 19th-century forts, and the stunning Maine coastline.

Charters depart from Portland’s Old Port and are perfect for families and small groups. Each charter is completely private for up to 6 guests, and all ages are welcome!

First round of drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the breathtaking views!

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early 19th century in Portland Harbor are always captivating. They are imposing reminders of days not too far gone when the defense of our coastline required their presence.

Despite their prominence, the forts are not easy to access for a variety of reasons, and most locals and visitors have never been to Fort Scammel, the only fort in the Harbor to see active combat. Fortunately, the owners of Fort Scammel have partnered with us to offer private tours of this incredible historic site. This is an experience NOT TO BE MISSED! Along the way, we’ll cruise past some of the other great sights in the bay, including the iconic lighthouses.

GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Our Fort Tour on a Private Island has a 4 PERSON MINIMUM to operate.

Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

The most immersive way to see Historic Portland is on foot. Our 60-minute walking tour takes you down the cobblestone pathways of our historic city in search of spirits that linger from times long past.

Our knowledgeable guides will enchant you with tales of Portland’s most renown ghosts as well as the area's vast and rich history. You’ll hear fascinating and spooky tales from the first European settlement in 1632 right up to the present day. Discover the many times Portland has fallen and risen anew, and hear about the restless spirits who remain, unable or unwilling to move on.

Follow our guides as they lead you by lantern-light sharing the ghost stories, legends, and folklore of this beautiful city. 

Walk With Ghosts in Portland

Have you seen these iconic beacons from the water? Now is your chance!
Board the Elizabeth Grace to cruise around Portland Harbor on this one of a kind sightseeing cruise. It is the perfect way to see the lighthouses, historic stone forts, and rocky islands that make Casco Bay a world-renowned destination. Relax with a drink as you take in the scenery!

GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Small Group Scenic Lighthouse Boat Cruise With Local Drinks

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the tranquil waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, cruising aboard Ruth is a unique adventure, a 39’ long classic, picnic style tour boat built in 1935 at Handy Boat in Falmouth, Maine.

Afternoon Lighthouse Cruise Along the Coast of Portland Maine

Experience historic architecture, harbor views, and rich seaside culture with this driving tour of Portland, Maine! Cross the cobbled streets of Old Port, chock full of shops, restaurants, and bars, all complemented by the sparkling bay. Dive into the city’s long and embattled history at a church still sporting British cannonballs. See iconic Maine lighthouses and visit pristine beaches. Portland may be a small city, but it packs a big punch!

Purchase one tour per car, not per person. Everyone listens together!

After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point.

Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months.

This isn't an entrance ticket. Check opening hours before your visit. 


Ultimate Portland Self-Guided Driving GPS Audio Tour

Discover the rich history and stunning architecture of the Portland peninsula. Only 3.5 miles long and 3/4 miles wide the Portland peninsula is packed full of food, history and culture. This 2.5-hour tour will show you the best of the peninsula.

Around The Peninsula Bike Tour

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. 

Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. 

You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. 

You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more. 


Audio Guided Walking Tour from Old Port of Portland, Maine

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking Maine sunset.

We’ll navigate through the islands of Casco Bay, passing by Portland’s most iconic coastal sights, including historic 19th-century forts, lighthouses, and the stunning Maine coastline.

This experience is perfect for families and small groups, offering a completely private and personalized tour just for you.

First round of alcoholic drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the view!

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you'll board a comfortable vessel equipped for a thrilling marine adventure. As we cruise along the rugged coastline, keep your eyes peeled for the majestic giants of the sea – humpback whales, fin whales, and minke whales are frequently spotted in these waters.

Our experienced naturalist guides will be with you every step of the way, providing fascinating insights into the behavior and biology of these incredible creatures. 

The tour also offers the opportunity to observe a variety of other marine life, including seals, porpoises, and a wide range of seabirds. Don't forget to bring your camera, as you'll want to capture these unforgettable moments. 


Maine Whale Watching Tour in Portland

Our 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble, before returning to the bike shop.

Two Hour Lighthouse Bicycle Tour from South Portland-Mellow

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. 
Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the tranquil waters of Casco Bay. 
All ages are welcome! Whether you are nine years old or 99, cruising aboard Ruth is a unique adventure, a 39’ long classic, picnic style tour boat built in 1935 at Handy Boat in Falmouth, Maine.

Morning Lighthouse Cruise Along the Coast of Portland Maine

Tasting oysters harvested from the ocean where they were grown is significantly different and better than eating them at an oyster bar, especially when you just shucked them! Freshness counts! This sea kayaking tour that teaches you the basics of sea kayaking on land before launching at Mere Point in Brunswick to visit a working oyster farm in NW Casco Bay!  After visiting the oyster farm, we'll stop on an island for your lesson on shucking, tasting, and snacks. Learn about aquaculture in Maine and how it improves the health of the bays.

Sea kayaking is an easy, fun way to sight see from the water.  We often see different kinds of sea gulls, cormorants, black and mallard ducks, eider ducks, great blue herons, snowy egrets, osprey and bald eagles. If we are lucky, we will see a seal. 

Paddlers of all ages will love exploring Casco Bay in this protected, scenic, historic area! No experience is needed. Single and double kayaks are used on this eco-guided tour by a Master Maine Guide.

Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses and our unique 14-passenger RIB boat is suited to tour the region while everyone gets a front-row seat so you can see and experience more of it. 

Learn about Portland’s nautical history, view wildlife like seals, harbor porpoises, and sea birds, and stop for photos at quintessential sights like all four lighthouses, Fort Gorges, seals, and the working waterfront while also escaping to lesser-known areas of the bay where wildlife viewing is the best. This is a unique tour that is unmatched in the breadth of its experience with a local captain to guide you and answer your questions about the region.

Please join us for the Best Of Casco Bay!



Guided RIB Boat Adventure of Casco Bay

The Portland Pubs Walking Tour is a leisurely 3-stop, 1 mile stroll through Portland’s Old Port neighborhood. This journey through history, narrated by the beverages inspired by Maine’s tenacious spirit, takes you past prominent landmarks and to our working waterfront.

Along the way, you’ll visit producers like Liquid Riot, a brewery and distillery that pays homage to the infamous Portland Rum Riots of 1855, and Shipyard Brewing Company, a cornerstone of Maine’s craft beer culture for over a quarter-century.

This bus tour’s final tasting will be held at Portland Beer Hub, the home of Maine Brews Cruise. Portland Beer Hub is a combo beer bar and retail space in the heart of the Old Port. The selection here includes beers from over 30 breweries across the state of Maine. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases!

Please note that tour stops may change without notice due to events and the availability of staff at each venue.

Portland's Old Port Breweries Walking Tour

Most recognize Portland, Maine for its vast selection of local craft breweries. And while we retain the title for ‘most breweries per capita,’ we’re experiencing profound growth in our craft beverage scene including a range of spirits and locally produced wine.

Neighborhoods like Portland’s East Bayside are brimming with craft beverage options to suit any taste, from Three of Strong’s small batch, organic rum to wines from Blue Lobster Urban Winery which are blended with Maine wild blueberries and apples from local orchards.

The third stop of the tour concludes at the Portland Beer Hub, the home of Maine Brews Cruise, and a blend of beer bar and retail space in the bustling heart of Portland’s Old Port. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases at the Portland Beer Hub.

Please note that tour stops may change without notice due to events and the availability of staff at each venue.

Portland's Best Craft Beverages Bus Tour

Experience the beauty, history, and charm of coastal Maine on this full-day adventure from Portland. Plan for 10–12 hours, with about three hours of travel each way. Scenic and photo stops break up the drive, but the main focus is exploring the Acadia area and Bar Harbor.

We’ll begin with a journey into one of Maine’s most scenic regions, known for rugged shorelines, crashing waves, sweeping overlooks, panoramic summits, and crystal-clear lakes.

Next, enjoy two hours in Bar Harbor—savor fresh seafood or a lobster roll, browse shops and galleries, grab ice cream, or stroll the waterfront and take in the views.

We’ll also visit the Fort Knox–Narrows Bridge Overlook for striking views of its soaring towers and the Penobscot River, then make a final stop in Bangor for a photo of Stephen King’s home—famous for its deep red Victorian style and eerie wrought-iron gates.

By day’s end, you’ll have experienced a rich mix of coastal beauty, history, and pop-culture highlights.

Bar Harbor and Acadia Full Day Private Tour from Portland

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experience!

Sunset Lighthouse Cruise Along Casco Bay

The Must-Do Sebago Lake Experience!

Explore the panoramic views of Sebago Lake with our unbeatable rental package! With our EZ Launch system, you'll enjoy easy access to launch right from our private site nestled between Panther Run stream and the north end of Sebago Lake. With your fitted life jacket, paddle and map in hand, you'll have endless opportunities to discover the lake's hidden coves, beaches, islands and wildlife.

Paddle along meandering streams before emerging into Sebago's scenic waters. Beach your vessel and savor a picnic lunch. Venture deep into secluded inlets to glimpse native wildlife. Or simply cruise the lake while soaking in Maine's iconic scenery. The varied landscape offers towering pines, rocky outcroppings and sandy beaches.

Ample parking, friendly staff, and convenient amenities like bathrooms and changing rooms, our facilities make Sebago Lake an ideal destination for a hassle-free day on the water. 

Half Day Kayak Rental on Sebago Lake

As we cruise the waters around Portland Harbor we will make stops at Portland Breakwater Light, Spring Point Light and Ram Island Ledge Light before stopping at Maine’s oldest and most iconic lighthouse, Portland Headlight. This historic beacon, with its striking architecture and stark coastal backdrop, is a sight to behold from the perspective of the Atlantic Ocean as seafarers have done for more than 200 years. After photos and information about this iconic lighthouse, we continue the ride along the rocky shores of Cape Elizabeth to Two Lights State Park, whose twin lighthouses perch atop dramatic cliffs.

Our best chance for wildlife comes during the next leg of the ride as we cruise open waters to Halfway Rock Lighthouse, a true maritime relic. Standing proudly on a remote ledge in the open ocean, it has guided mariners through thick fog and turbulent waters for over a century. Seals are often found hanging on the rocks and feeding in the nutrient-rich waters.

Seven Portland Lighthouses Tour

Private Casco Bay Cruise – Up to 5 Guests
Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves, spot local wildlife, and soak in the iconic charm of the Maine coastline.

Departures daily at 10 AM, 4 PM, and our most popular sunset cruise at 6:30 PM.

Sunset & Scenic Private Boat Tour of Portland & Casco Bay

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. 

(NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites).

All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. See Fort Gorges, Bug Light Park, and the beautiful Portland coastline. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Casco Bay Morning Windjammer Sail 

Step back in time to the bustling 18th Century port, where shipbuilding, trade, and whispers of strange occurrences at sea filled the air. Known for its picturesque waterfront, historic architecture, and vibrant arts scene, Old Port reveals its darker side at night. Supernatural tales include apparitions, psychic phenomena, and a sea serpent nicknamed Cassie.

2-Hour Portland Old Port Ghost Walking Tour

All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests. 

6 Hours Private Lighthouses and Kennebunkport Tour in Portland

Embark on an exclusive private tour of Maine's enchanting central coast and starting in the vibrant city of Portland. In just one day, immerse yourself in the region's finest highlights. Led by knowledgeable local guides, our private tours ensure an intimate and personalized experience. Marvel at the iconic Portland Head Lighthouse located in Fort Williams State Park and indulge in some retail therapy at the renowned L.L. Bean Factory Store. Cross the unique Androscoggin Swinging Bridge and explore the breathtaking Coastal Maine Botanical Gardens. Discover the charm of Boothbay Harbor. Immerse yourself in Maine's fascinating past at the historic Fort Edgecombe State Historical Site. Uncover stunning lighthouses, picturesque gardens, and charming coastal villages on this unforgettable day trip along Maine's central coast. 

Maine’s Mid Coast Private Day Tour from Portland 

Immerse in and interpret the natural beauty of Maine by capturing the moment in a painting. We will hike and paint on location. No experience necessary. This is an all level class that can be enjoyed by beginner painters as well as more experienced.

Paint Outdoors in Portland, Maine

Experience COLORFUL Maine on this 2-hour sightseeing tour, where you’ll take in the vibrant fall foliage and the best coastal sights in the Portland area. It doesn’t get any more “New England” than this!

This private charter is a flat rate for up to 6 guests—all ages welcome!

Step aboard MONHEGAN, our sturdy lobster boat, equipped with rollable side canvas for comfort even if the autumn air is crisp. Cozy up with the blankets we provide and enjoy an authentic New England experience.

To make your tour even more special, we’re including a round of drinks—choose from locally brewed Portland, Maine beer or a glass of wine as you soak in the breathtaking scenery.

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Savor the Flavors of Portland's Legendary Lobster Rolls on This Immersive Tour
- VIP Skip the Lines experience
- View and learn of working lobster boats and wharves to see how the freshest lobster is caught
- Sample the most mouthwatering, flavor-packed lobster rolls from Two of Portland's Top (while very different) purveyors
- Go behind the scenes at a waterfront lobster pound to learn the secrets of this iconic New England culinary delight
- Immerse yourself in the sights, sounds, and traditions of Maine's thriving lobster industry
-Includes (1) local craft Maine beer draft or water to wash down your fresh roll



Portland Lobster Roll Walking Food Tour – Waterfront Stories

Embark on an unforgettable boat tour of Casco Bay in Portland, Maine, where nature, history, and natural beauty intertwine. Our journey begins as we glide past the majestic Fort Gorges and historic Fort Scammel. When the tide permits, we are able to disembark onto Fort Gorges for a quick side-adventure. Next, we’ll cruise by the spark plug-style Spring Point Ledge Light perched on the granite breakwater of South Portland. 

The iconic Portland Head Light awaits us on the rugged cliffs of Cape Elizabeth, offering breathtaking ocean views followed by the eery and majestic abandoned Ram Island Ledge Light. We’ll then marvel at the stunning White Head Cliffs on Cushing Island and navigate through the scenic Diamond Pass, glimpsing all of Peaks Island's charm. Our adventure culminates at Half Way Rock, where we will hope to spot seals basking on their favorite sun-drenched rocks. Join us for this captivating tour, unveiling Maine’s rich heritage and natural splendor!

Sightseeing Boat Tour in Portland's Casco Bay Bird's Eye Maine

Welcome to Portland, Maine, a seaside gem bursting with history, creativity, and one of the most delightful food scenes in New England. Women only bakery walking tours invite you to slow down, savor the moment, and indulge in the city’s sweetest treasures. It’s the perfect brunch time activity for a bachelorette party, girl’s day out, or to connect with other women over pastries and coffee.

The West End is home to elegant 19th-century homes, tree lined streets, and a cozy, intimate vibe. Here you’ll find some of the city’s best cafés and award winning bakeries, where you’ll sample irresistible pastries and locally roasted coffee.

Whether you're visiting for the first time or rediscovering your own backyard, a bakery crawl is the perfect chance to soak up Portland’s vibrant culture. You’ll be led by McKenzie, a passionate local who’s created wedding cakes and dessert tables across Maine. Come hungry and bring your sense of adventure; Portland's best bites are waiting for you!

Portland, Maine West End Bakery Crawl - Ladies only!

Discover the sweetest side of Portland, Maine, on a female-only bakery crawl! Our coastal gem is known for its small-batch artistry, local ingredients, and unforgettable flavors. This is the perfect brunch-time activity for a bachelorette party, for a girl's day out, or to simply connect with other women over pastries and coffee!

Stroll from Munjoy Hill through the cobblestone streets of the Old Port, where historic charm meets a vibrant culinary scene. You'll visit beloved bakeries, sampling buttery croissants, seasonal pastries, creative confections, and locally roasted coffee.

Your guide, McKenzie - a pastry expert and baker who has crafted wedding cakes for countless Maine couples, will share her favorite bites and flavors of Portland’s best-kept culinary secrets.

You'll be making between 6-8 stops, so come hungry to indulge in a delicious adventure with like-minded women!

Portland, Maine East End Bakery Crawl - Ladies only!

Learn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay!  Often we paddle south to the end of Mere Point for a photo op and then on to visiting an island for a stretch break, snacks, and shoreline exploring. Then we paddle back on a different route close to an island to our launching point. Your Master Maine Guide will share history of the area while adapting the tour to paddling conditions and participants abilities.

Sea kayaking is an easy, fun way to sightsee from the water.  We often see different kinds of sea gulls, cormorants, ducks, great blue herons, snowy egrets, osprey and sometimes bald eagles. If we are lucky, we will see a seal. 

Paddlers of all ages will love exploring Casco Bay in this protected, scenic, historic area! No experience is needed. This a family-oriented experience. Single and double kayaks are used on this guided tour by a Master Maine Guide.

Sea Kayak to an Island Tour in Casco Bay

Explore the charm, history, and vibrant culture of Portland, Maine with this self-guided walking tour! Immerse yourself in the sights and sounds of this picturesque coastal city as you traverse the cobblestone streets of Old Port and downtown. Learn about the city’s long, embattled history as you pass the myriad of shops, bars, and eateries which have put it on the map. And discover secrets only locals know!

After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point.

Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months.

This isn't an entrance ticket. Check opening hours before your visit. 

Portland Maine Self-Guided Walking Audio Tour

Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone streets and admire old brick architecture by the waterfront. Visit bustling neighborhoods like Old Port and the Art District, stop at shops and restaurants whenever you please, and breathe in the coastal air. Then take a drive out to the east and west promenades, before swinging down to the famous Portland Head Light lighthouse. It’s the most comprehensive way to experience this unique, quirky city!

After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point.

Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months.

This isn't an entrance ticket. Check opening hours before your visit. 

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! 

Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

Portland, Maine Madness Scavenger Hunt

Join us for a private exclusive tour from Portland, Maine, to the breathtaking White Mountains of New Hampshire. Experience the region’s stunning waterfalls and historic towns with charming covered bridges, immersing yourself in New England’s natural beauty.

Choose between two exciting options:

 1. Historical Railway Experience: Ride the Mount Washington Cog Railway to the summit of Mount Washington, the highest peak in the Northeast. Enjoy breathtaking views as you ascend and learn about the railway’s rich history.
 2. Mount Washington Auto Toll Road Adventure: Opt for an extended tour up the Mount Washington Auto Toll Road, a family-owned route known for its spectacular vistas. This option offers fantastic views of the White Mountains as you drive to the top.

Book in advance, as this exclusive tour is likely to sell out quickly. Don’t miss your chance to experience the wonders of the White Mountains!

New Hampshire White Mountains Exclusive Private Tour

Introducing Portland’s World of Flavors Walk highlighting hidden gems and great flavors that give Portland its cosmopolitan flair. Enjoy this walkable city with a big palate on our international journey, tasting locally sourced foods prepared with the recipes, customs and spices from other lands.

On this 2.5-3 hour tasty romp through Portland’s historic Old Port and waterfront, you will enjoy the flavors while learning their food pathways and the owners journeys to Maine.

Portland’s World of Flavor serves up a diversity of tastes and ethnicities in a compact area, packing a punch of flavors you will love.

All tour experiences are highly educational and entertaining with trained, local guides.



Portland's World of Flavors Tour

Set off on a refined culinary adventure through the serene waters of Casco Bay. Your journey begins at Portland Beer Hub, where you’ll gather before being escorted to the waterfront to board your boat. As you glide past the stunning coastline, savor freshly shucked oysters perfectly paired with crisp prosecco. Whether you’re toasting to a special occasion or simply indulging in a moment of pure relaxation, this experience blends Portland’s finest flavors with breathtaking coastal views—an unforgettable way to enjoy the best of land and sea.

Portland Lighthouse Boat Cruise with Oysters & Prosecco

Step into the world of Let’s Roam, the undisputed champion of app-led scavenger hunts! Imagine strolling through city streets, hunting down top landmarks and uncovering secret gems, all while tackling brain-teasing trivia and thrilling challenges. Whether you’re collaborating with your crew or igniting friendly rivalry, every moment is a chance to learn something new and craft unforgettable memories.

From casual hangs to epic bachelorette blowouts, birthday bonanzas, or team-building triumphs, Let’s Roam Scavenger Hunts are the ultimate choice for adventure seekers of all kinds. Each player gets to choose their interactive role, ensuring everyone has a blast with challenges tailored just for them.

So, rally your squad, lace up your adventure shoes, and get ready to explore like never before with Let’s Roam! It’s time to turn any outing into an epic escapade filled with laughter, discovery, and the thrill of the hunt. Let’s make memories—let’s roam! 

Self-Guided Portland Scavenger Hunt: The Maine Event

Discover the charm of New England’s coast with a private tour from Portland, Maine, to Cape Ann and the North Shore of Massachusetts. This journey takes you to the stunning Castle on Crane Hill in Ipswich, offering views across expansive salt marshes and an immersion in historic grandeur. Next, explore Hammond Castle in Gloucester, a medieval-inspired estate filled with art, inventions, and captivating architecture.

Wander through the historic streets of Ipswich, where colonial homes and coastal views capture America’s early history. Then, enjoy a delightful stop at Russell Orchards, where you can stroll the orchards, savor fresh cider donuts, and sample wines made from their own fruit.

This exclusive tour combines majestic castles, authentic towns, and New England’s seasonal bounty—creating an unforgettable experience for those seeking a unique perspective on the North Shore. Join us for a journey that blends history, beauty, and local flavor into one perfect day.



Castles of Cape Ann, Massachusetts Private Day Tour 

Embark on an unforgettable day trip from Portland, Maine, where history and coastal beauty converge in an adventure that promises both excitement and intrigue. Begin your journey at majestic historical York where legends and tales of centuries past come to life. Next, step back in time at the Strawbery Banke Museum in Portsmouth, New Hampshire, where centuries-old homes and gardens transport you to a bygone era. Continue your journey to the picturesque town of Kennebunkport, where you can stroll through charming downtown, explore local shops, and savor the vibrant coastal atmosphere. Afterward, take a scenic detour to Marginal Way in Ogunquit, a stunning coastal walkway that offers breathtaking views of the Atlantic Ocean and rocky cliffs. Enjoy a leisurely walk along the paved path,. The day concludes at breathtaking York Beach, where Nubble Light stands sentinel over the rocky shore, this is a perfect end to a day filled with adventure and discovery.

Kennebunkport, York, and Portsmouth NH Private Day Tour

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds.
Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, and most recently Massachusetts. 

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

Our White Mountains Day Tour offers more than just scenic views—it’s a thoughtfully curated journey through New Hampshire’s most charming towns, historic covered bridges, and hidden natural wonders. Unlike larger, rushed tours, we keep our groups small for a more personal experience, allowing time to explore, photograph, and connect with each stop. From the iconic Kancamagus Highway to the massive Madison Boulder, every stop has a story—and our guides bring it to life. Guests also have the option to add a ride on the historic Mount Washington Cog Railway for an unforgettable summit experience.



New Hampshire White Mountains Day Tour

Learn the basics of stand-up paddle boarding on land before launching at Mere Point in Brunswick for a leisurely 2.5 hour morning tour of Northwest Casco Bay! We will paddle out to a demonstration oyster farm and then to an island to shuck and enjoy a complimentary tasting of the sweet and briny fresh Maine oysters.

Stand-up paddle boarding is a great, fun way to sight see from the water. We are likely to see cormorants, sea gulls, osprey, great blue herons, snowy egrets, ducks, and we might see fish jumping or a seal. 

Paddlers at least 12 years old will love exploring Casco Bay in this protected, scenic, historic area! There will be a break on land where we will stretch, taste the oysters and have some snacks that you bring.

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

Operation City Quest of Portland is a great way to see the city! Use an app to submit photos of items you find around the city and challenges you complete for points. The items and challenges can be completed in any order you prefer! See your score on the app leaderboard to see how you compare. The scavenger hunt includes a remote host to help via chat along the way. Come discover Portland.

Fun Scavenger Hunt in Portland, ME by Operation City Quest

All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger van that can take up to 12 passengers. We’re happy to customize the experience to match your interests. This particular tour covers all the major sights in Portland, followed by a visit to the South Portland lighthouses, including admission to Fort Williams Park to see the Portland Headlight. After exploring Portland, you'll journey down the highway to Kennebunkport, a charming coastal village that served as the summer retreat for former President George W. Bush and his family. While we have a standard route, as a private tour, we can personalize the itinerary to suit your preferences.

Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. 
Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, and most recently Massachusetts. 

Casco Bay: Private Afternoon Charter on Heart's Desire

Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean views, and savor local flavors. With a personalized itinerary, this tour offers the flexibility to explore at your own pace, while an expert guide provides insights into each destination. Enjoy a relaxed atmosphere with included snacks, bottled water, and lunch to keep you energized throughout the day.

- Private tour lasting approximately 7 to 8 hours
- Customizable itinerary to suit your interests
- Included lunch, snacks, and bottled water
- Pickup from your location in an air-conditioned vehicle

Kennebunkport, York and Portsmouth NH Private Tour

Join us for an exciting **Private Coastal Tour from Portland to Camden**, exploring the beauty and history of Maine’s coastline! 

Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. 

In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is **Camden Hills State Park**, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mount Battie.

We'll finish with a brief stop at the Maine State Capitol, designed by the same architect as the U.S. Capitol, offering a fascinating glimpse of Maine’s history.

This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

Camden, Rockland, Pemiquid, and Belfast Exclusive Private Tour

Get ready for an unforgettable photographic journey through Portland iconic destinations! We’ll guide you on a relaxed exploration of the town most photogenic landmarks, showcasing the best Portland has to offer.

Alongside our professional photography services, we’re thrilled to share insider tips to enrich your holiday experience. You can choose between a 30-minute or 1-hour photoshoot, allowing you to customise your experience to best suit your needs. Join us as we uncover Portland hidden gems and well-kept secrets, all while capturing the unforgettable moments of your vacation. We can’t wait to meet you and embark on this adventure together!

Private Professional Vacation Photoshoot in Portland

Step back in time and immerse yourself in the rich history of Portland, Maine, with this engaging walking tour through the heart of the city. Your expert guide will lead you through Portland’s charming streets, sharing stories of its colonial past, the rise of its maritime industry, and its key role in American history. As you stroll through the Old Port and waterfront, you’ll discover historic landmarks, cobblestone streets, and unique architecture that reflect Portland’s vibrant heritage. This tour is perfect for history enthusiasts and anyone wanting to explore the captivating story of one of Maine’s most iconic cities.

Portland's Old Port Historical Walking Tour

Step into the shadows of Portland’s past on this thrilling true crime tour, where secrets lurk behind historic facades and cobblestone streets whisper tales of corruption, violence, and vice. From ruthless mobsters and bootleggers to power-hungry bosses and shocking scandals, this tour unveils the darker side of Maine’s largest city. Walk the very streets where speakeasies thrived, deals were made in the dead of night, and blood was spilled in the name of power. Led by expert guides, this journey through Portland’s underworld will leave you with spine-tingling stories you won’t soon forget. Dare to explore the city’s past? Book now—if you’re brave enough.

True Crime in Portland's Old Port - Evening Walking Tour

Holly Jolly Hunt is a scavenger hunt that is played using an app on your smartphone, that brings your entire family and friends together for holiday cheer. During the adventure you’ll be seeking out all the traditional, and even the non-traditional holiday items we all see this time of year around the city. You’ll get points for each item you find. The goal is to capture as many items as you can in order to score as many points as possible and get 1st place on the leaderboard. Along the way you’ll be asked to perform silly holiday themed tasks meant to bring laughter and smiles to everyone involved. Come play with us. Young or old, this is a scavenger hunt for everyone that enjoys this time of year. We promise you will create holiday memories that you will not forget! Holly Jolly Hunt can be played in any city!


Holiday Scavenger Hunt in Portland by Holly Jolly Hunt

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands.

Guests are encouraged to help raise the sails with a deckhand and steer the ship for themselves. Your charter is your time to relax, celebrate, entertain, and sail, so you get to set the pace and atmosphere. Beer, wine, and other alcoholic beverages are permitted on board.

Portland Tall Ship Private Charter on Casco Bay

100% Private Charter for Groups up to 15 — Flat Rate Pricing

This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate experience on Casco Bay. Unlike crowded public cruises, your group of up to 15 guests will enjoy the full comfort and charm of one of our classic wooden vessels—all to yourselves.

Cruise past iconic lighthouses, historic granite forts, and stunning stretches of Maine’s coastline, with opportunities to spot harbor seals, seabirds, and other local wildlife along the way. Whether you’re celebrating a special occasion or simply gathering with friends, this charter offers a personalized, relaxed way to experience the best of coastal Maine.

Feel free to bring your own food—we provide all the glassware, plates, and utensils you’ll need. Local craft beer, wine, and other beverages are also available for purchase onboard, making it easy to sip, savor, and soak in the scenery.

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

Come sailing aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire is 100 years old this year and has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine. 

This two-hour private, morning sail is the perfect way to experience Maine's coastline. Whether you are interested in getting married in an intimate setting, a special way to celebrate a reunion, birthday or anniversary, or just want to enjoy sailing at its finest, step aboard and plan an event never to be forgotten!

2 Hour Private Morning Charter on Heart's Desire in Casco Bay

Bar Harbor and Acadia Full Day Private Tour

Experience the beauty and history of Ipswich and Cape Ann on this private tour. Wander Castle Hill’s grand estate, explore Ipswich’s heritage, and enjoy Gloucester’s seaside character. When available, Hammond Castle offers an unforgettable glimpse into medieval architecture on the New England coast. End your journey at Russell Orchards for fresh, local charm

Castles of Cape Anne, Massachusetts - Private Day Tour

Unlike large group bus tours, this experience is designed to be personal, flexible, and immersive. You’ll walk the streets of Salem with a knowledgeable guide who doesn’t just point out landmarks but brings their stories vividly to life—from the haunting legacy of the Witch Trials to the maritime wealth that built the city, and the literary genius of Nathaniel Hawthorne.

What makes this tour unique is the balance of history and atmosphere: you’ll explore centuries-old cemeteries and mansions, admire harbor views and gardens, and even encounter touches of pop culture like the Bewitched statue. With small groups and a customizable pace, you’ll have the freedom to linger where your interests lie most—whether it’s taking photos, diving deeper into Salem’s legends, or enjoying a quiet moment in a hidden garden.

This isn’t just sightseeing—it’s a chance to experience Salem’s past and present through stories, scenery, and atmosphere in a way that big tours can’t match.

Private Day Tour of Salem MA, from Portland ME

Experience the beauty of Maine’s central coast on a fully private, all-day tour designed just for you. Unlike crowded bus tours, our small-group experience offers personalized attention, comfort, and flexibility. Travel in style through autumn-kissed landscapes as your local guide leads you to handpicked highlights—like the iconic Portland Head Light, the charming harbor town of Boothbay, and the historic Fort Edgecomb. Walk the gently swaying Androscoggin Swinging Bridge, shop at the legendary L.L.Bean Flagship Store, and take in riverside views in Bath, “The City of Ships.” This is coastal Maine at its finest—tailored, immersive, and unforgettable.

Maine's Mid Coast Private Day Tour from Portland

This isn’t just another sightseeing trip—it’s a curated journey through Maine’s most iconic landmarks and hidden gems, woven together into one unforgettable day. From the elegance of Portland Head Light, the nation’s most photographed lighthouse, to the playful charm of Eartha, the world’s largest rotating globe, every stop reveals a different facet of Maine’s character. Guests walk a historic suspension bridge built by the engineers of the Brooklyn Bridge, explore the state’s proud maritime heritage in Bath, and visit the legendary L.L. Bean flagship store in Freeport.

What sets this tour apart is the balance of scenery, history, and culture: stunning coastal views, hands-on heritage at museums and memorials, and Maine icons you won’t find grouped together anywhere else. And because it’s a shorter itinerary, it’s the perfect choice for cruise ship passengers or travelers with limited time who still want a rich, memorable Maine experience.

The Maine Experience: Coast, Culture & History

Book your private transfer from Portland International Jetport (PWM) to Portland hotels and return.

Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer.

Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.

• Meeting with a Nameplate
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers

Portland Jetport (PWM) to Portland - Round-Trip Private Transfer

Experience the stunning beauty of Casco Bay on a personalized intimate (up to 6 guests per trip), public 2-hour powerboat cruise. Whether you're looking for a scenic sightseeing tour, an up-close encounter with Maine’s wildlife or a journey through the region’s rich maritime history, this exclusive charter is designed to provide an unforgettable adventure.

Departing from the working waterfront, you’ll glide past busy wharves lined with lobster boats, ferries, and historic brick buildings that reflect Portland’s seafaring heritage. From the start, the mix of city energy and natural beauty sets the tone for an unforgettable journey on Casco Bay.

Seals often bask on rocky ledges, ospreys and bald eagles soar overhead, and in the summer months, porpoises sometimes surface alongside the boat. Whether it’s spotting seabirds, breathing in the salty ocean air, or simply enjoying the thrill of the ride, a powerboat cruise from Portland offers both adventure and relaxation in equal measure.


2 Hour Scenic Powerboat Cruise Experience Portland's Waterfront

Book your Private Transfer from Portland Cruise Port to Portland International Jetport (PWM).

Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport/port transfer.

Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.
Our transfers will provide you with such services: meeting with a name plate, door-to-door delivery, no hidden fees, clean cars and professional drivers, which will make your trip more comfortable and safe. We guarantee the quality of the services provided.

Private Transfer from Portland Port to Portland Jetport (PWM)

Discover the best of Portland’s vibrant wine scene with the Portland Walking Wine Tour. Perfect for wine lovers and curious explorers alike, this leisurely walking tour takes you through the city’s charming streets to three handpicked wine-centric shops. At each stop, you’ll indulge in curated tastings of exceptional wines, from local Maine favorites to acclaimed international selections. Your expert guide will enrich your experience by sharing captivating stories about each wine’s origins, tasting notes, and winemaking processes. Enjoy a relaxed and refined atmosphere while connecting with fellow wine enthusiasts, making this tour an engaging way to savor Portland’s unique flavors and culture. Book your spot today to experience an unforgettable journey through Portland’s wine destinations!



Portland Old Port Wine Tasting Walking Tour

Start your experience with a guided tasting at a top local brewery, where you’ll sample a selection of expertly crafted beers. Then, gear up for an adrenaline rush as you test your skills with an hour of axe-throwing excitement—no experience needed, just a sense of adventure! After proving your aim, unwind and celebrate with another round of local brews at a second brewery, soaking in the vibrant flavors and atmosphere. Whether you’re a beer connoisseur, a thrill-seeker, or just looking for a unique outing, this experience promises fun, excitement, and great company!

Portland Axe Throwing and Two Local Breweries Van Tour

Indulge in the bold flavors of Portland on this mouthwatering tour. Start with a refreshing craft beer tasting at a local brewery, then dig into a hearty BBQ feast at a popular spot known for its savory dishes. Finally, cap off your experience with a visit to sample locally crafted spirits. Perfect for food and drink enthusiasts, this tour delivers a satisfying trio of Portland’s finest flavors—craft beer, delicious barbecue, and small-batch booze.

Portland's Best Barbecue, Brewery, and Distillery Van Tour

Include a private car for you, your family and friends visiting the Monkie And sloths sanctuary Here you will have the extraordinary opportunity to get up close with this amazing creatures in a safe environment. You’re well explore the century and take memorable pictures and how fun after that you also have a private guide that would take you to any other destination, you choose. You also have option to spend time on the beach

Monkeys and sloths, private tour , and beach

Book your private Arrival transfer from Portland International Jetport (PWM) to Portland hotels.

Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.

Our transfers will provide you with such services: meeting with a name plate, door-to-door delivery, no hidden fees, clean cars and professional drivers, which will make your trip more comfortable and safe. We guarantee the quality of the services provided.

Portland Jetport (PWM) to Portland - Arrival Private Transfer

Book your private Departure transfer from Portland hotels to Portland International Jetport (PWM).

Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.

• Meeting with a Nameplate
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers

Portland to Portland Jetport (PWM) - Departure Private Transfer

Book your Private Transfer from Portland Cruise Port to Portland city hotels or any addres. 

Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door port/city transfer.

Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.

• Meeting with a Nameplate
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers

Private Transfer from Portland Cruise Port to Portland city

Comfort Transfer from Portland city hotels to Portland Cruise Port up to 15 passengers (For party over 7 passengers can be provided one big minibus or two minivans).

All Vehicles fully licensed and insured. Our cars are equipped with all necessary facilities for a trip to any part of the world under any weather conditions, including additional fastenings for sports and other equipment.

On request for your tourists, we have child seats for all ages. Vehicles are clean inside and outside; our drivers’ always are well dressed and always pay attention to our guests. They speak English. They will meet you with a name sign; help with luggage and on arrival to the port.

Our transfers will provide you with such services: meeting with a name plate, door-to-door delivery, no hidden fees, clean cars and professional drivers, which will make your trip more comfortable and safe. We guarantee the quality of the services provided.


Private Transfer from Portland city to Portland Cruise Port

Experience Portland’s newest tasting tour from the creators of the city’s original donut walk, featured in the Boston Globe. Get a taste of the city's sweet side during this guided afternoon walking tour featuring artisan donuts and craft drinks from some of the city’s most beloved spots.

You’ll stroll scenic downtown streets while enjoying four flavors from two donut shops, complimented by tasting-size pours of local select beer, cider, cocktails, or mocktail options. 

Along the way, your guide will share how the donut was born at sea off the coast of Maine, sprinkle in local foodie insights, and reveal fiery tales from Portland’s ‘Inferno Years’ that shaped the city’s flavor and resilience.

Perfect for:
 Pre-happy hour fun
 Girls’ weekends & bachelorette groups
 Couples & curious foodies
 Instagram-worthy photo ops

Portland Walking Tour Craft Beverages, Local Lore and Donuts

It is the only regularly operating pedicab in Portland. Portland Pedicab creates the feeling of joy for all by allowing passengers to spend the time viewing Portlands scenery while heading to their destination. This is a great mode of transportation for those that like to be outside! Music which is provided, is always an option while enjoying the views of Portland. 

Portland Pedicab Taxi Reserve 

Immerse yourself in Portland’s rich maritime culture on this scenic walking tour through the city’s historic wharfs. As you stroll along the bustling waterfront, indulge in a delicious seafood snack at an iconic local spot while soaking in the sights and sounds of the working docks. Along the way, our expert guides will share captivating tales of shipwrecks, fishermen, and the city’s deep connection to the sea. From the charm of the Old Port to the breathtaking coastal views, this tour is the perfect way to experience Portland’s nautical history—one bite and story at a time.

Old Port Working Waterfront Walking Tour and Seafood Tasting

This yoga class is not just movement — it's a multi-sensory, coastal escape. Set against the serene backdrop of Casco Bay, you'll flow through an all-levels class while breathing in salt air, feeling the ocean breeze on your skin, and hearing the soft call of a distant foghorn.

I offer a thoughtfully curated experience that blends mindful movement, nervous system support, and deep relaxation. We’ll move together through gentle stretches and grounding flow, and end with a lavender-soaked towel, optional hands-on assist during savasana, and a locally sourced treat to take with you.

This is more than just yoga — it’s an invitation to slow down, reconnect with your body, and find peace on the coast of Maine.

Coastal Flow A Maine Yoga Experience

Use an app to survive a zombie apocalypse in Portland . In Zombie Scavengers, explore the city however you'd like to search for items needed to survive a zombie apocalypse. You'll get points for finding these items. You can also do some zombie themed challenges for points on the app as well. Strategize in order to get the most points and survive the apocalypse. Your remote host will be there for you via chat if you need anything. Can you survive the apocalypse in Portland?

Scavenger Hunt in Portland, Maine by Zombie Scavengers

During Crazy Dash of Portland, you'll use an app and walk through the city to collect points by finding items around the city and performing challenges. You can find the items in any order you want. Check out the rankings in the app to see your score compared to other teams across the nation. Crazy Dash comes with a remote host to chat with you in case you need anything. Crazy Dash is our most relaxed scavenger hunt. Come explore with us in Portland!

Scavenger Hunt Adventure in Portland by Crazy Dash

Explore Portland with Wacky Walks royal scavenger hunt. In our app-based scavenger hunt, your group will participate in competitions to become the King or Queen of your group throughout the game. The active King or Queen will lead the other players to find items around the city and complete fun tasks. For every item you find and task you complete, you will receive points. The goal of Wacky Walks is to stay the King or Queen for the longest and gain as many points as you can. Take your time playing Wacky Walks, there is no time limit and you can play in any area of the city you would like. There will be a remote host that will be chatting with you during the game in case you need anything. Come be the King or Queen in Portland for the day!

Unique Scavenger Hunt Experience in Portland by Wacky Walks

Walk around Portland while completing the 3Quest Challenge scavenger hunt! Use our app to find a list of objects (provided in riddle form) around the city and participate in fun challenges for points. Collect points and take a look at your score compared to others on the app's leaderboard. All of the objects and challenges will be divided into 3 quests. Complete the 1st quest, 2nd quest, and 3rd quest, in order, to complete the game! Set a time limit of 2 hours for yourself if you'd like to make the challenge even more intense! During the game, you'll have a remote host who will follow along virtually with you and chat if you need any help! Come explore Portland with us by completing all 3 Quests!

Experiences in Portland, Me, United States Of America