If you’re considering a visit to Charlottesville and want to experience its renowned wine scene without the hassle of navigating alone, a private wine tour might just be your best bet. Based on glowing reviews and detailed itineraries, this five-hour journey offers a relaxed, intimate way to sample Virginia’s best vinos.
What we love about this experience? First, the personalized approach lets you pick your stops or leave the recommendations to your guide—perfect for those who want a tailored day. Second, the guide’s knowledgeable and friendly attitude consistently earns praise, making tastings engaging and fun.
One potential consideration is the price point—at $235 per person, it’s an investment, especially if you’re traveling solo or as a couple. But when you factor in private transportation, the variety of wineries visited, and the quality of the experience, many find it’s worth it.
This tour suits travelers who prefer a comfortable, flexible, and guided way to explore the vineyard-rich Monticello region. Whether you’re a wine novice or a seasoned enthusiast, this experience can adapt to your interests.
Key Points

- Personalized Experience: Choose your preferred wineries or rely on expert recommendations.
- Convenience: Private, air-conditioned transportation makes getting between vineyards stress-free.
- Experienced Guides: Friendly and knowledgeable guides enhance the experience with their insights.
- Beautiful Scenery: Expect scenic views and historic ruins as part of the tour.
- Flexible Itinerary: Stops include lesser-known vineyards and historical sites, giving a well-rounded taste of the region.
- Cost: At $235 per person, it’s a premium experience but offers tailored, hassle-free wine tasting.
What To Expect from the Charlottesville Private Wine Tour

This tour is designed to give you a balanced look at Virginia’s wine country, centered around the Monticello wine region. It’s a private experience, so the group is small—your own party—making it more personal and relaxed. The tour spans roughly five hours, starting at noon, with a focus on comfort and quality rather than rushing.
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The Pick-up and Transportation
From the moment you’re greeted, the emphasis is on ease. The transport is an air-conditioned vehicle, making the roughly 5-hour drive comfortable even if the weather is warm. The tour begins in Charlottesville, and the pick-up is flexible for most travelers, situated conveniently for those staying locally.
Guests rave about the private aspect—no rushing with strangers, and the guide is available for questions or personalized stops. The water bottles provided are a nice touch for staying refreshed, especially if you’re sipping wine all afternoon.
Exploring the Wineries: A Closer Look
Merrie Mill Farm and Vineyard
Your first stop is Merrie Mill Farm & Vineyard in Keswick, a cozy tasting room known for its approachable hospitality. Founded by Guy and Elizabeth Pelly, Merrie Mill offers a quirky yet welcoming atmosphere that appeals to those who love a bit of character in their wine experience.
Visitors have praised the warm, friendly vibe and the delightful setting. The tasting here lasts about 1 hour 40 minutes—ample time to chat with the staff, explore, and enjoy some wines without feeling rushed.
Barboursville Vineyards and Historic Ruins
Next, you’ll visit the historic Barboursville Vineyards, which combines beautiful grounds, historic ruins, and a broad selection of wines. This estate is a highlight for many, partly because of the chance to stroll around the ruins of Thomas Jefferson’s mansion, adding a touch of history to your tasting.
Guests mention that the tastings are continuous in the Discovery Tasting Room or through seasonal pairings in the Library 1821. The splendid lawns surrounding the ruins are perfect for a picnic if you bring your own food (note: food and beverages are not included in the tour price).
The informative hosts and the variety of wines, from current vintages to older bottles, make this a worthwhile stop. As one traveler put it, “we visited wineries we never would have found on our own,” highlighting the value of guided exploration.
Southwest Mountains Vineyards
The third stop is Southwest Mountains Vineyards, a newer but well-regarded vineyard that emphasizes the terroir of Virginia’s Monticello AVA. The wines are thoughtfully crafted by a skilled team, and many visitors find that their bottles make excellent gifts or special occasion drinks.
Expect to spend around 1 hour 40 minutes here, tasting a range of wines and soaking in the beautiful scenery. As one reviewer noted, “each wine showcases the extraordinary terroir,” making it a favorite for those interested in wines that reflect Virginia’s unique landscape.
What We Think About the Experience

From the reviews and itinerary details, this private tour hits many of the right notes. The small group size and personalized approach make it suitable for those who prefer a relaxed, intimate experience.
The guides consistently receive high marks for their friendliness and knowledge, creating an environment where you feel comfortable asking questions and exploring the wines at your pace. One traveler summed it up, “Jeremiah went above and beyond,” which hints at the level of service you can expect.
The scenic stops—especially at Barboursville’s historic ruins—and the opportunity to enjoy Virginia’s beautiful vineyards and lawns add visual appeal alongside the tasting experience.
Pricing at $235 per person may seem steep, but considering the private transportation, multiple winery visits, and personalized service, many find it aligns well with the value. If you’re looking for an all-in-one, stress-free way to enjoy Virginia wine country, this tour offers a lot for the cost.
Who Is This Tour Best For?
This experience works well if you’re someone who appreciates flexibility and comfort. It’s ideal for couples, small groups, or friends who want to avoid the hassle of planning and driving. Because it’s private, you can tailor the stops or simply enjoy a leisurely day with a guide taking care of logistics.
Travelers interested in historic sites combined with wine tasting will also enjoy the stop at Barboursville’s ruins. It’s suitable for those who enjoy scenic views and well-curated wine selections without feeling rushed.
It might be less perfect for travelers on a tight budget or those looking for a larger group experience—this is a premium, intimate outing designed to be personalized.
Practical Details and Final Thoughts
The tour begins at 12:00 pm in Charlottesville, and the confirmation is immediate upon booking. Since all food and beverages are not included, you might want to bring some snacks or plan to buy some at the vineyards—many visitors do enjoy a picnic in the lush lawns.
The free cancellation policy offers peace of mind, allowing you to cancel up to 24 hours in advance for a full refund.
This private Charlottesville wine tour offers an engaging, relaxed way to enjoy Virginia’s wine country, especially if you value personalized service, beautiful scenery, and learning about local wines from passionate guides.
Private Charlottesville Area 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!”
Frequently Asked Questions

Is the tour suitable for all travelers?
Most travelers can participate, and the private nature makes it adaptable. It’s designed to be comfortable for a wide range of guests, with no strenuous activity involved.
How long does the tour last?
It’s approximately 5 hours, starting at noon, with a relaxed pace to enjoy the wineries and scenery.
Are food and beverages included?
No, food and beverages are not included, but you’re welcome to bring snacks or purchase at the vineyards.
What’s the price for this tour?
It’s $235 per person, which covers private transportation, a knowledgeable guide, and visits to three wineries.
Can I customize the stops?
Yes, you can choose your preferred vineyards or rely on the guide’s recommendations for a personalized experience.
Is transportation comfortable?
Yes, the tour uses an air-conditioned vehicle, making it easy to relax between stops.
What makes this tour special?
The combination of private, customizable visits, scenic views, historic sites, and friendly guides creates a memorable, tailored experience.
Do reviews support the quality of this tour?
Absolutely, with a 5-star rating from 15 reviews praising the friendliness, knowledge, and overall enjoyment of the experience.
Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.
If you’re looking for a laid-back, personalized way to experience Charlottesville’s wine region, this private tour seems to deliver on all fronts. It’s perfect for those who want to avoid the crowds and enjoy Virginia’s wineries at their own pace, with expert guidance to enrich the journey.


