
5 Hour Historic Thomas Jefferson Wine Tour
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.8/5
Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is 5 Hour Historic Thomas Jefferson Wine Tour worth booking?
5 Hour Historic Thomas Jefferson Wine Tour is a 5-hour experience in Charlottesville, United States, from $270 per person. It scores 56 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.8/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 56 / 100
- Rating
- 4.8/5 (5)
- Duration
- 5 hours
- From
- $270 per person
We would like to personally invite you to join us on an unforgettable journey through the beautiful countryside of Charlottesville and the surrounding area. As you enjoy tastings of some of Virginia's finest and most cel
What you get
About this experience
We would like to personally invite you to join us on an unforgettable journey through the beautiful countryside of Charlottesville and the surrounding area. As you enjoy tastings of some of Virginia's finest and most celebrated wines, you will be completely immersed in the rich history shaped by Thomas Jefferson’s lasting influence on the region. This experience promises to be both relaxing and enlightening, blending the natural beauty, exquisite flavors, and historical depth unique to this area.
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
The Rotunda, located at the far end of Academic Village, is where you will be dropped off. A self-guided walking tour map and informational leaflet pertaining to the Rotunda and Academic Village will be given to you. After 30 minutes, we will go back to the drop-off location to pick you up.
30 minutes here
Jefferson Vineyards
Enjoy a wine tasting for one hour at Jefferson Vineyards. This is the original site of Jefferson and Philip Mazzei's effort to make wine.
60 minutes here
Gordonsville
Your guide will point out the Exchange Hotel and other historically significant locations as we drive through Gordonsville.
Pass by without stopping
Barboursville Vineyards and Historic Ruins
At Barboursville Vineyards, you can partake in wine tastings and eat at one of the two restaurants. You can explore the ruins of the Barboursville Estate before or after lunch.
105 minutes here
Enjoy wine tastings at this beautiful winery
60 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
- Specialized infant seats are available
- Public transportation options are available nearby
- Infants and small children can ride in a pram or stroller
- Suitable for all physical fitness levels
Photos






What travelers are saying
Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.
The guide
3 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
5 verified traveler reviews for 5 Hour Historic Thomas Jefferson Wine Tour. Ratings and reviews provided by Viator and Tripadvisor.
Top Notch Tour
My husband and decided to take a long weekend and do a wine tour. We both like history and so we chose the Historic Thomas Jefferson wine tour. It was lovely! Keith was our driver and he was friendly and professional and a great driver. The owner, Jeremiah, was communicative beforehand to make sure I knew what to expect and how to identify our driver, etc. Seems like a great tour company and I would highly recommend Old Crowe Tours and this wine tour.
Response from the operator: Thank you again for another wonderful review, I really appreciate it! And again, I'm so glad you both had such a great experience with us on your tour.
via Viator
Thomas Jefferson wine tour
Great tour, Jeremiah was very accommodating and gave us plenty of time at each stop. He made sure we were all set at each winery so we could bypass the crowds.
Response from the operator: I'm so glad that you all had such a wonderful time on your tour with us. I had a great time meeting and laughing with everyone!
via Tripadvisor
Very knowledgeable and...
Very knowledgeable and pleasant host. Also flexible with itinerary. Would've loved to have included Veritas winery instead of Keswick.
Response from the operator: I'm sorry, if I had known that you wanted to see Veritas Vineyard then I would have been more than willing to accommodate your request. I hope that you enjoyed the rest of your tour with us.
via Viator
GREAT experience! highly revommend
we had a fantastic experience on this tour. Love that it started by exploring the Rotunda at UVA and our guide Jeremiah was extremely knowledgeable in the history. Then even though it was a two winery tour, he got us into a third winery so we could experience as much as possible. Jeremiah was very friendly and knowledgeable and went out of his way to make us feel important. Even while driving between wineries, he filled us in on the local history and what makes Charlottesville Charlottesville. would highly recommend.
Response from the operator: I really appreciate that Eric! I had a great time meeting you and your wonderful wife, and thank you for inviting me along on your anniversary weekend celebration. Go Cowboys!!
via Tripadvisor
Great way to experience Charlottesville area
My friend and I had only a couple of days to work with and wanted to experience as much of the area and some wineries, as possible on a tour. This one was perfect. Our very personable guide, Jeremiah, provided great information on the area and some highlights and also took us to three different wineries to experience tastings. It was a great day.
Response from the operator: Oh, I'm so glad that you two had such a great time. It was wonderful to meet you both and I hope to see you again!
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
- 2
- Verdict
- Worth a Look
Why this scores 56
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
5 Hour Historic Thomas Jefferson Wine Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Charlottesville.
How much does 5 Hour Historic Thomas Jefferson Wine Tour cost?
+
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 5 Hour Historic Thomas Jefferson Wine Tour take?
+
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 5 Hour Historic Thomas Jefferson Wine Tour worth it?
+
It holds an Outty Ranking of 56 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.8/5 across 5 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 5 Hour Historic Thomas Jefferson Wine Tour?
+
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 5 Hour Historic Thomas Jefferson Wine Tour suitable for kids and families?
+
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 5 Hour Historic Thomas Jefferson Wine Tour?
+
Around 2 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?
+
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 5 Hour Historic Thomas Jefferson Wine Tour start and how do I get there?
+
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?
+
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 Charlottesville Area Wine Tour. 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?
+
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?
+
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?
+
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.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for 5 Hour Historic Thomas Jefferson Wine Tour.
Pick your date




