Charlottesville Wine Tour: Jefferson & Barboursville tastings

Taste wines at two vineyards while your guide connects the history

A 5-hour guided wine tour in Charlottesville pairs tastings at Jefferson Vineyards and Barboursville Vineyards with a self-guided walk through the Rotunda and Academic Village, where Thomas Jefferson's influence shaped the region. The tour includes private transportation, an air-conditioned vehicle, water bottles and a knowledgeable English-speaking guide; food and beverages beyond the tastings are on your own.

Step-by-step itinerary

Historic wine tasting tour in Charlottesville

• Arrive at the Rotunda
• Self-guided walking tour of Academic Village
• Pick up from Rotunda
• Drive through Gordonsville, see Exchange Hotel
• Wine tasting at Jefferson Vineyards
• Wine tasting and lunch at Barboursville Vineyards
• Explore Barboursville Estate ruins
• Wine tasting at final winery

The Experience

Charlottesville's wine country sits in the shadow of Jefferson's legacy, and this tour threads both together. You start at the Rotunda, the centerpiece of the University of Virginia grounds that Jefferson designed, where you get a self-guided walking map and spend 30 minutes exploring the Academic Village on your own before your guide picks you up. From there, the day moves into wine: a full hour of tastings at Jefferson Vineyards, the original site where Jefferson and Philip Mazzei tried to establish Virginia winemaking in the 18th century.

The drive to Barboursville Vineyards takes you through Gordonsville, where your guide points out the Exchange Hotel and other historically significant buildings along the way. At Barboursville, you have time for wine tastings and the option to eat at one of two on-site restaurants; you can also explore the ruins of the Barboursville Estate, a brick structure that burned in 1884 and now stands as a landmark on the property. The tour wraps with tastings at a third winery, rounding out the afternoon with Virginia wines.

Transportation is private throughout—your own vehicle and driver rather than a group shuttle—which means the pace stays flexible and the stops don't rush. The vehicle is air-conditioned, and water bottles are provided. Children from age 1 are welcome, and specialized infant seats are available if you need one.

What’s included

• Private transportation in an air-conditioned vehicle.
• wine tastings at Jefferson Vineyards and Barboursville Vineyards.
• a self-guided walk through the Rotunda and Academic Village with map and informational leaflet.
• a knowledgeable English-speaking guide.
• water bottles.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by Ole Crow Tours

Is this one for you?Five hours leaves room for a leisurely afternoon—the self-guided Rotunda walk, two full tastings, lunch if you want it, and time to explore the Barboursville ruins—without eating the whole day. If you need to fit other Charlottesville stops into your schedule, this tour's fixed duration and private transport mean you're not waiting for a group or a shuttle to move on.

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Top questions

What exactly is at the Rotunda that I'll be walking through?

The Rotunda is the centerpiece of the University of Virginia's Academic Village, designed by Thomas Jefferson. You get a self-guided walking map and an informational leaflet, then spend about 30 minutes exploring the grounds on your own before your guide returns to pick you up.

Do I get to taste wine at all three places the itinerary mentions?

Yes. You taste for one hour at Jefferson Vineyards, then at Barboursville Vineyards you can do tastings and eat lunch at one of two restaurants on-site, and the tour ends with tastings at a third winery.

Is lunch included, or do I pay separately at Barboursville?

Lunch is not included in the tour price. At Barboursville Vineyards, you can choose to eat at one of the two restaurants there at your own cost, or you can skip it and focus on the tastings and the estate ruins.

Will the guide speak English the whole time?

Yes, your guide is a live English speaker who will narrate the historical sites and the drive through Gordonsville, and answer questions about the wineries and the region.

Can I bring my young children on this tour?

Children are welcome from age 1 onward. Specialized infant seats are available if you need one, and the air-conditioned vehicle and water bottles make the five-hour day manageable for small kids.