Monticello Wine Tour: Personalized 5-Hour Experience

A day in wine country is essential for any Charlottesville trip, but picking the right wineries can be challenging if you’re not acquainted with them. Enjoy a customized, five-hour wine tour of the Monticello Wine Region in a more private setting. Select your favorite vineyards, explore hidden gems, or let us suggest stops that match your preferences.

Duration: 5 hours
Cancellation: 24 hours
Highlights

Merrie Mill Farm and Vineyard - 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.

What's Included
  • Private transportation
  • Water Bottles
  • Knowledgeable and Friendly Guide
  • In-vehicle air conditioning
What's Not Included
  • All food and beverages
Location
Merrie Mill Farm and Vineyard
Merrie Mill Farm
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(11 Ratings)
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1 star
Berthiel2025
Mar 24, 2025
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.
Review provided by Tripadvisor
M4677rasydneys
Mar 1, 2025
Great day - Benjamin was great! He was so accommodating and helpful. We enjoyed the selection of wineries and views. Thank you ole crow tours!
Review provided by Tripadvisor
Haileymw2236rh
Feb 2, 2025
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!
Review provided by Tripadvisor
Wine_enthusiast1
Jan 27, 2025
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!!!!
Review provided by Tripadvisor
F8119azdavidp
Dec 2, 2024
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.
Review provided by Tripadvisor
Spacer13
Nov 1, 2024
Amazing Winery Tours with a Fantastic person - Jeremiah is a fantastic person to explore Charlottesville wineries. He customized the route as per our needs. The vehicle was fabulous and his company was great. Highly recommended.
Review provided by Tripadvisor
Helen_j
Oct 26, 2024
Charming minibus wine tour - Jeremiah went above and beyond! We had an amazing wine tour, recommendations and nice chatter. And thanks for helping to build our fire pit!
Review provided by Viator
Rina_c
Sep 14, 2024
So fun! - So much fun!! We went to three vineyards and loved all of them. Talking with everyone on the bus was amazing.
Review provided by Viator
Tammy
Sep 8, 2024
Fantastic Fun! - Had a wonderful experience with Jeremiah! He shared a lot of knowledge about the area we were in, had a fantastic bus that was clean and well stocked, and was very accommodating!! Couldn’t have asked for a better trip! Thanks Jeremiah!!
Review provided by Tripadvisor
Dougdl4927rh
Aug 26, 2024
Driven to three different winerys near Charlottsville VA - We had such a fun day with Jeremiah! He could not have been nicer. The ride out to the wineries was beautiful. And we were able to enjoy the wine tastings knowing that we were in safe hands. His suv was extremely comfortable and clean. What a pleasure it was to meet Jeremiah. We highly recommend Ole Crow tours. Doug and Jackie
Review provided by Tripadvisor
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up to 14 guests
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April 2025
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