Private Charlottesville Area Wine Tour

Summary: Excellent tour! We visited four wineries with a focus on white wines. Jeremiah was very accommodating and offered good insights on the history of the region as well as some of the wineries we visited. He was always waiting which gave us flexibility to adjust our timing as the day progressed. Highly recommend for a comfortable and safe experience through the wine country!

Summary: This 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.

Summary: Excellent 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.

Summary: We 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!

Summary: The 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.

Summary: Jeremiah 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

Summary: HIGHLY 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.

Summary: I 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 jtolley@olecrowtours.com 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.

Summary: No 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

Summary: The tour was good and the wineries we stopped at were good. My only issue is that most every place we went to asked if we had a reservation (one place you had to have one to even go in their tasting room) so I feel like for the money we spent the company should be able to get us reservations. At least that is how it has been on other private tours that I have done in Charlottesville.