
Private Charlottesville Area Wine Tour
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 29 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Charlottesville Area Wine Tour worth booking?
Private Charlottesville Area Wine Tour is a 5-hour experience in Charlottesville, United States, from $270 per person. It scores 72 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 5/5 rating across 29 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 72 / 100
- Rating
- 5/5 (29)
- Duration
- 5 hours
- From
- $270 per person
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
What you get
About this experience
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.
What's included
Included
- Private transportation
- Water Bottles
- Knowledgeable and Friendly Guide
- In-vehicle air conditioning
Not included
- All food and beverages
What you'll see and do
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.
100 minutes here
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.
100 minutes here
Thoughtfully crafted by our skilled and renowned winemaking team, each wine showcases the extraordinary terroir of Virginia’s Monticello AVA. For that perfect glass or beautiful bottle to celebrate special occasions, Southwest Mountains Vineyards wine will be a wonderful addition to any day.
100 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Ends at
Within 25 miles of Charlottesville
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 14 travelers per booking
- Operated by
- Ole Crow Tours
Know before you go
- 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
Photos






What travelers are saying
Outty’s summary of the themes that recur across 29 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
6 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
4 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
29 verified traveler reviews for Private Charlottesville Area Wine Tour. Ratings and reviews provided by Viator and Tripadvisor.
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.
Response from the operator: Thank you so much for your kind words; that was amazing! I wish I had the pleasure of driving you all myself for your tour, but I'm thankful Keith did a good job. I'm thrilled that you had a wonderful day, and we hope to see you all again sometime.
via Viator
Great experience. ...
Great experience. Visited some excellent spots. Ride was clean and comfortable. Will go back and do it again one day
Response from the operator: Thank you so much; I'm glad that you enjoyed your time with us. Come back and see us anytime!
via Viator
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!
Response from the operator: I'm thrilled that you all had such a great time, I did as well. Thank you again!
via Tripadvisor
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!
Response from the operator: Thank you so much for your kind words. It was wonderful meeting both of you, and I'm thrilled that you all had such a great experience with us!
via Tripadvisor
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.
Response from the operator: Thank you so much for your kind review. It was wonderful meeting you both, and I'm so glad that you enjoyed your tour with us.
via Viator
Good to know
- Duration
- 5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $270 to $275
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 10
- Verdict
- Strongly Recommended
Why this scores 72
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Charlottesville Area Wine Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Charlottesville.
How much does Private Charlottesville Area Wine Tour cost?
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Prices start at $270 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Charlottesville usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Charlottesville Area Wine Tour take?
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Plan for about 5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Charlottesville is not rushed.
Is Private Charlottesville Area Wine Tour worth it?
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It holds an Outty Ranking of 72 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 29 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Charlottesville, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Charlottesville Area Wine Tour?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Charlottesville Area Wine Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Charlottesville Area Wine Tour?
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Around 10 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Charlottesville can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Charlottesville and add a light layer if any part of the 5-hour experience runs outdoors or after sunset.
Where does Private Charlottesville Area Wine Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Charlottesville within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Charlottesville?
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Charlottesville, VA packs its best experiences into walkable neighborhoods, local food, and day trips nearby. Outty ranks every bookable tour and activity in Charlottesville by rating quality, review depth, booking demand and value, so you can see the standouts before you book. On Outty we rank every Charlottesville experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Virginia Private Custom Wine Tour from Charlottesville, Shenandoah National Park Self-Guided Driving Audio Tour, Private Wine Tours Transportation from 3 People and More. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Charlottesville?
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Spring and fall bring the best weather and lighter crowds in Charlottesville, while summer has the widest choice of tours and evening activities. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Charlottesville?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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