Wine - Friendly and informative. Our driver knew the area and was flexible. He provided us with some good information about the area.

Amazingly Curated Celebration - 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

We had a wonderful day touring the wineries - We had a wonderful time with Ole Crow Tours, the company that conducts this private wine tour. I'll be using them again next time I visit the area. First, the team there is a pleasure to work with. Ole Crow makes the tour all about you. There were 5 of us spending a weekend in Staunton, VA and we wanted to experience a day of wine tasting in the beautiful Monticello and Shenandoah wine region. None of us knew much about the region. Jeremiah, the owner, was so helpful in customizing a tour. He listened to what we wanted, made great suggestions for wineries, food options, scenery, and atmosphere to help us narrow down our list. They make a reservation so the winery is expecting you when you arrive. We lucked out and had Jeremiah as our driver that day. He dropped us off at the winery entrance and we spent about 60-90 mins at each. I believe they are flexible on how much time you spend at each. Then we would hop back in the comfortable SUV and we were on our way to the next. Could not be easier and no one had to worry about driving. Highly recommend!

A Spring Wedding at Boar’s Head Resort - First visit to Charlottesville VA for a friend.’s wedding. We decided to take in the historical nature of this location by visiting the University of Virginia and the memoirs of Thomas Jefferson in the Rotunda building on campus. We then visited his home—Monticello—an architectural masterpiece designed by Jefferson—even though he wasn’t’ a trained architect. We visited various wineries including the beautiful Trump winery. Of special note was dinner at Fleurie, a downtown Charlottesville French restaurant. A special dinner experience!

Beautiful, relaxing weekend. - The was great. This was a last minute idea to explore Virginia wine country. Beautiful.!!!! You can not go wrong with this tour group.

Great day - Benjamin was great! He was so accommodating and helpful. We enjoyed the selection of wineries and views. Thank you ole crow tours!

Amazing Day of Wine Tasting - The wine was amazing! Jeremiah was awesome! He was so helpful in arranging and then rearranging our trip when our plans changed. The wineries were in beautiful locations! We were very happy with our experience!

Jeremiah was the best designated driver EVER!!! - This was the best decision ever!! Jeremiah helped me plan my surprise itinerary for my husband’s birthday and was incredibly responsive and helpful. His gorgeously clean car picked us up and drove us to 3 amazing locations. Jeremiah knows so much about the area and kept us entertained and cared for the entire afternoon. I plan on using Ole Crow Tours every time I make a wine tasting trip to Charlottesville. Cannot recommend enough!!!!

Ole Crow Makes the Show - Wow, what a great day! Ole Crow were the perfect hosts for our Friendsgiving Show. We had plenty of time to enjoy great wine and wonderful venues with friends just before Thanksgiving. The places they suggested were the perfect sites to match what we had in mind. I can’t wait for the next time we do this.

Good - 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.