This 5-hour, private custom tour features 3 to 4 winery visits, luxury Sedan, tasting room recommendations, and an experienced personal Wine Trail guide. Add-on lunch options are available after reserving your tour. Inquire with our team to learn more, after reserving, to learn about food options and pricing.

Virginia Private Custom Wine Tour from Charlottesville

A very comfortable and stylistic a tour and tasting some of Virginia’s finest vineyards and wines. 

It’s very private and enjoyable for couple looking for an intimate getaway, a small group celebrating a special occasion, a bridal party, or a business team looking for a change of scene. You are making the right choice to experience the natural beauty of Mountains while driving to one of the best winery in historic Charlottesville. It is an exciting time of touring and wine tasting. Your vehicle type will depend on your group size.


Private Wine Tours (Minimum 3 & Maximum 6 ) Pickup Maximum 30 Mi 

Ole Crow Tours warmly invites you to explore the very best that Virginia’s renowned wine region has to offer in comfort and style. Simply sit back, relax, and let us handle all the details, carefully ensuring a seamless and unforgettable experience for you and your guests to truly savor every moment.

On this thoughtfully curated tour, you’ll be enjoying visits to 3 carefully selected wineries located on the scenic eastside of Charlottesville. This journey will take us through the charming Keswick area, once home to Thomas Jefferson’s old stomping grounds, a region rich with history, natural beauty, and timeless elegance.

Private Charlottesville Area Wine Tour

Charlottesville has experienced its fair share of turmoil and tragedy, alongside its charming streets and delectable cuisine. From the legend of the enigmatic Moon Ghost who terrorized a local family to the brooding figure of James Madison reported at his beloved Montpelier, the Charlottesville area has been haunted by the shadow of death and destruction for centuries. A bone-chilling stroll at night exposes the enduring existence of the city’s distressing past.

This spine-tingling ghost tour will take you to some of the most haunted spots in the city. From the former home of a murdering husband to chilling experiences at a local park, you will delve into the shadows of Charlottesville's murky history.

This is a walking tour. We do not ever the private homes or businesses. The duration of the tour is outside and the total tour time is account for us walking from spot to spot. 

Chains, Coffins, & Curses: Charlottesville Ghost Tours

When you book a tour with, you get the leading tour provided within the the Monticello Wine Trail Region. Depending on group size, day of the week, our group can help get you access to some of the best tables at vineyards, guide you on dining options, and talk you through the history and landmarks of the area. 

Custom Wine Tour In Black Suburban With Panoramic Sunroof

Discover the legacy of Thomas Jefferson on this full-day guided tour to Monticello, his historic estate perched atop a scenic mountaintop in Charlottesville, Virginia. Explore the architecturally stunning home where Jefferson shaped the ideals that defined a nation, filled with personal artifacts, inventions, and writings. Stroll through his lush gardens, a blend of natural beauty and botanical experimentation. Gain insight into plantation life and learn the stories of the enslaved individuals who lived and worked at Monticello, offering a deeper understanding of America’s past. Admission includes entry to museum, exhibits, and historic grounds for a well-rounded experience. With expert guidance and comfortable transportation, this tour is perfect for history lovers and cultural explorers. Enjoy a smooth, hassle-free journey with air-conditioned transport and convenient pickups from Washington, D.C., Rockville, MD, or Falls Church, VA—making it easy to step into history for the day.

Small Group Washington DC to Thomas Jefferson Monticello Day Tour

Let’s Roam is the #1 app-led adventure hunt company. Explore the best landmarks and hidden gems, answering trivia questions and tackling challenges along the way. Team up with your friends or go head-to-head as you uncover fascinating facts and create unforgettable memories. 

Let’s Roam Adventure Hunts are perfect for any occasion—whether it's an everyday outing, a bachelorette bash, a birthday celebration, or a corporate team-building extravaganza! Each player gets to choose an interactive role, with unique challenges for everyone. Ready for an adventure? Let's Roam!


Self-Guided Scavenger Hunt: Centuries of Charlottesville

Please join our knowledgeable, entertaining guides in an unparalleled tour of the best of food and culture on the world-famous UVA Corner.

The UVA Corner Food Tour: Private Walking Food Tour in Charlottesville

Witness America the Beautiful with this bundle of 30+ national park tours! Lush wilderness, staggering mountains, jaw-dropping geysers, and more—this bundle has it all! You’ll find all these in this one package:

• Grand Canyon
• Yellowstone
• Grand Teton
• Rocky Mountain
• Shenandoah
• Acadia
• Sequoia & Kings Canyon
• Joshua Tree
• Arches
• Bryce
• Canyonlands
• Capitol Reef
• Zion
• Grand Staircase
• Monument Valley
• Great Smokies
• Death Valley
• Olympic
• Badlands
• Glacier
• Yosemite
• Everglades
• Saguaro
• Petrified
• Red Rock Canyon
• Mt. Rainier

After booking, check your email to download the separate Audio Tour Guide App by Action, enter your unique password, and access your tour. These steps require good internet/Wi-Fi access. From there, follow the audio instructions and the route.

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.

30+ National Parks Self-Guided Driving Tours Bundle

If you want to overload your senses, this could be the one. This tour combines two of the area's top vineyards, which not only produce wonderful wine but also provide an unforgettable culinary experience. One of the stops is also recognized for its architectural design, while the other for its architectural ruins. 

Wine and Culinary Delight Private Tour

The Downtown Mall Food Tour is a unique and memorable way to visit one of America's top college towns.

The Downtown Mall Food Tour

We would like to personally invite you to join us on an unforgettable journey through the beautiful countryside of Charlottesville and the surrounding area. As you enjoy tastings of some of Virginia's finest and most celebrated wines, you will be completely immersed in the rich history shaped by Thomas Jefferson’s lasting influence on the region. This experience promises to be both relaxing and enlightening, blending the natural beauty, exquisite flavors, and historical depth unique to this area.


5 Hour Historic Thomas Jefferson Wine Tour

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!

Charlottesville Challenge Scavenger Hunt

With scenic, gently sloping hills leading to one winery after the next—not to mention historic attractions, lavish accommodations, and fine food—Charlottesville, Virginia, is the ideal destination for those seeking a wine-centric experience.
Nestled between Richmond and Washington, D.C., it’s a perfect road trip destination for East Coasters looking for an easy and fun adventure (or anyone looking to take in Virginia’s gorgeous forests and scenery). These five wineries in the Charlottesville region offer exceptional wines, along with vibrant character and rich history.


Charlottesville: Best Vineyards Private Tour (Up to 14 people)

Leaving from Boar's Head Resort adventure into the George Washington National Forest to Bald Mountain Jeep Trail.

The Trail adventures are off-road, the duration is approximately 4-6 hours, with a peak elevation of 4000+ ft above sea level. 4x4 is the only way to access these breathtaking locations, as the trails are steep and challenging year-round. This is for the truly adventurous; those who seek challenges and crave excitement. 

Jeep includes a Refrigerator, Camp Kitchen, Skottle, Awning, Camp Chairs, and even a toilet. Everything you need to have an enjoyable day in the George Washington National Forest is included. Bring your lunch, beverages and we will stop to eat.

Boar's Head Resort Off Road Jeep Tour

Skip the stress and confusion of finding a taxi upon arrival at the Charlottesville International Airport. Instead, book this private airport transfer service and enjoy convenient, reliable, comfortable private transportation from the airport to your destination.Just relax and leave the driving to us. Transfer services are available 24 hours a day, seven days a week. Choose from a Luxury Sedan transfer for 3 passengers or a 6 passenger SUV.

Private Arrival Transfer from Charlotteville Airport (CHO)

This exceptional tour takes us to two of Thomas Jefferson's most iconic masterpieces, the University of Virginia and Monticello, both honored as UNESCO World Heritage sites in 1987 for their outstanding cultural significance. Our journey begins with a detailed guided tour of the picturesque University Lawn and the distinguished Rotunda at the University of Virginia, where history and architecture blend beautifully. Next, we head to Monticello's David M. Rubenstein Visitor Center, a thoughtfully designed space featuring an excellent gift shop and numerous engaging exhibitions dedicated to Thomas Jefferson and the rich history of Monticello. For a convenient and pleasant break, you can enjoy a quick bite and refreshing drink at the Monticello Farm Table Cafe before proceeding to your in-depth guided tour of the historic estate.

Private UNESCO World Heritage Tour

Keeping Families and Groups and make them happy.

Special rides for groups and families like: Surprise Excursion for couples; Concert/Events; welcome/Farewell ride; School groups etc. N/B the rate for this service is per person Families and Groups are picked at their places or at our Pantops Shopping Center Sub Station to Various Destinations. The first 1hour will be used to travel to the Destination of the group or families. The next 3 hours customers will engaged in their group or family activities example music concert, social gathering, games etc. Customers will be accounted for and take them back to their places or our Pantops Shopping Center sub-Station.

Family Wine Tour

The Dairy Market is among Charlottesville's leading food, retail, and entertainment venues. Free parking is available onsite. 

Experiences in Charlottesville, United States Of America