Private Tour
Private Charlottesville Area Wine Tour
Overview
Available languages
5 hours
Mobile ticket
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.
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Private transportation
Water Bottles
Knowledgeable and Friendly Guide
Air-conditioned vehicle
All food and beverages
Meeting and Pickup
Pickup points
Select a pickup point
What To Expect
Merrie Mill Farm & Vineyard is a tasting room destination in Keswick, VA. Founded by Guy and Elizabeth Pelly, Merrie Mill reimagines the tasting room experience by marrying a devotion to warm, approachable hospitality with a weird, wonderful setting that delights and inspires.
Barboursville Vineyards and Historic Ruins
The entire estate is open for tasting our wines in a stroll or in a picnic, and our informed and enthusiastic hosts present tastings continuously in the Discovery Tasting Room, every day of the week, as well as in Library 1821, . The Tasting Room is where the broadest range of our current vintages is introduced, while the Library 1821 presents a changing selection of flights of current and older vintages from our cellars, and with seasonal culinary pairings designed by our chefs. Every encouragement is given, also, to enjoying our wines in the truly splendid lawns surrounding the historic Landmark Ruins of Thomas Jefferson's mansion for Governor James Barbour, a pleasant stroll away.
Options
Private Charlottesville Area Wine Tour
Pickup included
Reviews
24 reviews
Total reviews and rating from Viator & Tripadvisor
You will not regret booking this Private Wine Tour!!!
caitlinpR3261ET,
Oct 17, 2025
- Review from Tripadvisor
5.00This is 100000000% worth it! This was such an amazing experience for us as a couple celebrating our 2nd anniversary. My husband and I were pleasantly surprised and excited to learn that we would have a private driver, which made the experience so much more personal and fun! The wineries we visited were absolutely gorgeous and each unique to their own style and vibe. Photographers: You CAN absolutely bring your cameras for the views!!! I added my edited photos from the trip as well. Our Driver, Keith, was wonderful and so personable, and he made the experience awesome. We had a blast and I would absolutely do this again, with different wineries to try! The owner was wonderful as well in communicating with us as to what our itinerary would be, and ensuring our location was updated.
Excellent service
A3161NNericab,
Oct 15, 2025
- Review from Tripadvisor
5.00Excellent service!! Jeremiah was very knowledgeable and extremely helpful knowing where we should go. Also able to adjust to what we wanted to see and do.
Highly recommend
H5904QKjenniferp,
Aug 24, 2025
- Review from Tripadvisor
5.00We did a girls trip to Charlottesville and this was the highlight of the weekend. Jeremiah was amazing as a driver. The SUV was clean, he was a safe driver, very personable and showed us all the sites. Even made reservations for us at all of the wineries. Definitely recommend!
Great way to spend an afternoon!
Sandra B,
Aug 13, 2025
- Review from Viator
5.00Great way to spend an afternoon -- Jeremiah was great to chat with in the car as he took us to several wineries where the food, ambience, and wines were well worth experiencing.
Great atmosphere and vibe!
Heather R,
Aug 2, 2025
- Review from Tripadvisor
5.00The BEST wine tour! Jeremiah was so knowable and picked out the perfect day! It was awesome - you can’t go wrong! He is so knowledgeable and picked out the best wineries.
Must do tour while in Charlottesville
randyk68,
Jul 26, 2025
- Review from Tripadvisor
5.00Jeremiah was absolutely the best tour guide. He picked us up at our hotel in Charlottesville and took us to three wonderful wineries that he suggested. We were visiting the area so we didn’t have a particular winery in mind. However, he would have been willing to go to a specific one if requested. We spent about 75 -90 minutes at each winery. He was a wealth of knowledge of each winery and history of the area. If you’re ever in Charlottesville this is a must do tour to take. A great stress-free way to visit wineries and not worry about driving
Highly Recommended- Excellent service/company. Thanks, Jeremiah!!!
C S,
Jun 28, 2025
- Review from Tripadvisor
5.00HIGHLY RECOMMEND!!! Like a friend driving you. Jeremiah was wonderful from the first email inquiry. We were a couple visiting Charlottesville, particularly around Monticello, for a big birthday. Visited four wineries. Jeremiah was great in advance for taking our requests and preferences and designing a wonderful itinerary. One small winery he recommended (shout out to Hona Lee!!! Family run, great wine, super friendly) turned out to be our favorite!!! Super professional, beautiful sparkling clean and cool touring vehicle; arrived early; communicative; flexible; knowledgeable; and a fantastic conversationalist. We REALLY enjoyed our trip and meeting Jeremiah. Highly recommend to any couple or small group of friends looking for a truly personable, welcoming, and professional guide/experience. 5 stars!!! Can’t wait to do again sometime.
Ole Crow Tours of Greater Charlottesville
FellowTraveler738561,
Jun 28, 2025
- Review from Tripadvisor
5.00I wanted to create a great trip for my 50+ year old high school friends when they visited on June 24, 2025. Jeremiah, owner of Ole Crow Tours was professional, punctual, friendly, flexible and informative. It was the hottest day of the summer so far and Jeremiah made sure his spacious, impeccable clean vehicle was cooled down before we embarked on our adventures and in between stops. Jeremiah also had plenty of cold water bottles at our disposal. I think we drank them all! We were on a fairly tight schedule so timing was of the utmost importance. Jeremiah made sure we stayed on track. The tour and stops we made were perfect. Visit his website [email protected] and you will find all kinds of tours or if you want to create your own he is happy to accommodate. It was a great day and a home run for my friends. Thank you Jeremiah and Old Crow Tours.
Wine
Roland M,
Jun 10, 2025
- Review from Viator
5.00Friendly and informative. Our driver knew the area and was flexible. He provided us with some good information about the area.
Amazingly Curated Celebration
Islandscouts,
May 26, 2025
- Review from Tripadvisor
5.00No matter what kind of adventure you envision—whether it's Hot Air Ballooning, leisurely Golf, or indulgent Wine Tours custom-tailored to your tastes—look no further than Jeremiah Tolley at Ole Crow Tours. I initially contacted Jeremiah through email, outlining specific preferences for wines and a memorable dinner for my wife’s birthday surprise. He orchestrated an experience that exceeded all our expectations. Our journey began with an engaging area history, followed by a delightful tour of Meri Mill Winery, accompanied by live music and exceptional wines. Afterward, we were ushered away in his immaculate and stunning SUV to our next destination, Barboursville Vineyards. There, we strolled the beautifully maintained grounds and explored the historic ruins, which added a unique charm to our visit. When the time came for our culinary experience, we were taken to the estate where, in an intimate gathering, we enjoyed a multi-course meal perfectly paired with exquisite wines. This was more than just an outing; it was a thoughtfully curated adventure that made for an unforgettable celebration. Thank you, Jeremiah, for such a wonderful adventure
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Operated by Ole Crow Tours