Monticello Wine Tour: Personalized 5-Hour Experience

Discover Charlottesville’s wine country with a personalized, five-hour tour. Choose your vineyards or get expert recommendations for an intimate wine-tasting experience.

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
Additional Information

Ole Crow Tours cordially invites you to discover the finest offerings of Virginia’s celebrated wine region in both comfort and style. Simply unwind and let us take care of every detail, ensuring a smooth and memorable experience for you and your companions to enjoy every moment to the fullest.
This meticulously planned tour includes visits to three…

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
(29 Ratings)
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Chris_s
Jul 9, 2026
An Enjoyable Afternoon Made Possible by Ole Crow Tours - Ole Crow Tours makes wine touring convenient and easy to schedule. Let me explain: Our group of 4 were staying at a B&B in Orange - a location not normally on their list for tour pickups but when asked via email if they could manage this, within moments they replied back that they would indeed pick us up at this location with no additional charge. Fast and easy. When the day of our scheduled tour arrived, Keith our driver for the afternoon, was super prompt and out of the van ready to assist us get comfortable on our way to the 1st of 3 destinations. Reservations had already been made by Ole Crow Tours at all 3 of our winery destinations so no wait, no fuss - just prompt seating and enjoyable tastings pared with food at all 3 stops. (Food and wine are not included in the cost of the private tour so be sure to bring payment for those items that you'll consume.) Ole Crow Tours scheduled us to visit 3 wineries during our 5 hour tour which covered a range of venues and styles. Each stop offered its own vibe and unique character and each showcased the splendid wines and hospitality of Virginia's premier wine country. We appreciate the professionalism of Ole Crow Tours throughout the planning and execution phases of our trip. We would recommend them to anyone interested in winery tours without the risk of drinking and driving. This is the way to go.
Review provided by Viator
Noel_s
May 13, 2026
Great experience. ... - Great experience. Visited some excellent spots. Ride was clean and comfortable. Will go back and do it again one day
Review provided by Viator
Rebekalu
May 6, 2026
Wine tasting and so much more! - We toured local vineyards for two days with Jeremiah. He arrived promptly each day in a very comfortable van. We enjoyed the information he provided regarding the area and vineyards as we traveled. The vineyards were diverse and the wines provided great variety with something for everyone. The views from the vineyards provided an unexpected bonus! Thanks Jeremiah!
Review provided by Tripadvisor
Texas_guy57
Mar 29, 2026
Knowledgeable & Experienced… Perfect! - 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!
Review provided by Tripadvisor
Julian_w
Mar 21, 2026
Cozy tour - Relax, engage with the driver, and let him know your likes. This isn't their first rodeo and they can guide you and provide advice.
Review provided by Viator
Caitlinpr3261et
Oct 17, 2025
You will not regret booking this Private Wine Tour!!! - 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.
Review provided by Tripadvisor
A3161nnericab
Oct 15, 2025
Excellent service - 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.
Review provided by Tripadvisor
H5904qkjenniferp
Aug 24, 2025
Highly recommend - 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!
Review provided by Tripadvisor
Sandra_b
Aug 13, 2025
Great way to spend an afternoon! - Great 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.
Review provided by Viator
Heather
Aug 2, 2025
Great atmosphere and vibe! - 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.
Review provided by Tripadvisor
From $111
up to 14 guests
2 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).