Charlottesville’s 5 Best Wine Tours

Charlottesville is a standout destination for wine lovers thanks to its vibrant Monticello Wine Trail and scenic Blue Ridge backdrop. Its combination of historic charm, diverse vineyards, and welcoming tasting rooms makes it a perfect place for a wine excursion. Our curated list of the best wine tours combines top-rated experiences based on reviews, value, and unique features—whether you’re after a personalized private outing, a guided group tour, or a luxurious vehicle with panoramic views. From the flexibility of a custom private tour to intimate vineyard visits, you’ll find options tailored to different tastes and budgets.

In this guide, you’ll discover detailed descriptions of each tour, highlighting what makes them stand out. We cover everything from private excursions with exclusive access, like the Virginia Private Custom Wine Tour, to more affordable group experiences such as the Private Charlottesville Area Wine Tour. Plus, explore options that combine wine tasting with culinary delights or even a luxury vehicle with panoramic sunroof for a more stylish adventure. Read on to find the perfect wine tour to match your style and expectations.

1. Virginia Private Custom Wine Tour from Charlottesville

This private tour (review page) consistently earns a perfect 5-star rating from over 570 reviews, which says a lot about its popularity. For $499 per group (up to 3), you get a 5-hour tailored experience with a private chauffeur leading you through Virginia’s Blue Ridge Mountains and countryside. What makes this tour stand out is the flexibility—you’re in control of which 3 to 4 wineries to visit, making it ideal for those with specific favorites or a desire for discovery.

The tour begins with a scenic drive in a vehicle suited to your group size, offering free bottled water along the way. You can choose to enjoy a picnic lunch at one of the vineyards, adding a relaxed, personal touch to the day. The guide, Gillie, is praised for her professionalism and local knowledge, enhancing the experience. Guests mention it’s perfect for couples, small groups, or bridal parties wanting a customized day in wine country.

The value here is high, considering the private transport, multiple tastings, and the chance to curate your own itinerary. It’s especially suited for those wanting intimacy, flexibility, and a relaxed pace. The main drawback? The price is higher than other options, but the personalized service and private chauffeur make it worthwhile.

Bottom Line: For those craving a tailored, stress-free wine day with privacy and the option to picnic, this private custom tour delivers a top-notch experience.

2. Private Charlottesville Area Wine Tour

This personalized group tour (review page) also earns a perfect 5-star rating from 15 reviews. Priced at $235 per person, it offers an approximately 5-hour experience exploring the Monticello Wine Region. What sets this apart is the ability to choose your preferred vineyards or rely on expert recommendations, making it a flexible, intimate way to experience the local wine scene.

It includes a visit to Merrie Mill Farm & Vineyard, a charming spot founded by Guy and Elizabeth Pelly, known for its welcoming atmosphere and unusual, inspiring setting. The tour emphasizes personal choice—you can select the wineries you want to visit or ask the guide to suggest lesser-known gems. The focus is on quality and local flavor, with guided tastings and the chance to learn about Virginia’s wine history.

Guests rave about the friendly guide Jeremiah and how the tour felt like spending a day with friends. It’s ideal for couples or small groups seeking a relaxed, customizable experience without the private chauffeur’s expense. The main limitation is the per-person cost, but considering the hands-on experience and curated visits, it offers excellent value.

Bottom Line: If you want a flexible, tailored tour with the ability to select your favorite vineyards and enjoy an authentic, personal experience, this tour hits the mark.

3. Custom Wine Tour In Black Suburban With Panoramic Sunroof

This luxury private experience (review page) costs $549 per group (up to 6) and lasts about 5 hours. The tour’s highlight is the black suburban vehicle with a panoramic sunroof, perfect for taking in the scenery as you glide through the Monticello Wine Trail. It’s a top choice for those who want style, comfort, and a personalized itinerary.

The tour is fully customizable, with stops at 3-4 wineries or breweries, depending on your preferences. The guides help you access some of the best tables and can assist with dining options or answer questions about the local landmarks. It’s suitable for groups that prefer a private, high-end experience with flexibility and a touch of luxury. The tour’s focus on customization means it’s perfect for celebrating special occasions or simply indulging in a more upscale outing.

Guests mention the excellent driver service and the panoramic views as highlights. While the cost is higher, the personalized itinerary, luxury vehicle, and private guide justify the premium for travelers seeking comfort and exclusivity.

Bottom Line: For those wanting a luxury, customizable tour with panoramic views and flexible stops, this private experience offers a memorable, stylish day.

4. Private Wine Tours (Minimum 3 & Maximum 6) Pickup Maximum 30 Miles

This affordable private tour (review page) costs $85 per person and is perfect for small groups (minimum 3, maximum 6). It lasts about 5 hours and includes pick-up and drop-off within 30 miles of Charlottesville. This tour emphasizes personalized itineraries with a dedicated guide taking you to the Monticello Wine Trail, with stops at 3-4 wineries.

Guests praise the friendly driver and the ease of not having to worry about driving or planning logistics. The tour includes guided tours of each vineyard, where you can learn about winemaking and purchase wines directly. It’s an excellent choice for travelers on a budget or those who want a straightforward, private experience without sacrificing personal attention.

The reviews highlight how well the guide adapts to individual preferences and creates a relaxed, intimate atmosphere. The price point makes it a good value for groups looking for customized experiences without the luxury price tag.

Bottom Line: If you want a personalized, private vineyard visit at a reasonable price, this tour provides a flexible, hassle-free option.

5. Wine and Culinary Delight Private Tour

This combo experience (review page) costs $235 per person for about 5 hours of wine tasting and culinary pleasures. It’s ideal for those who want more than just wine—this tour includes visits to two top vineyards, one known for its architectural design, and the other for its historic ruins.

The tour features guided tastings at Barboursville Vineyards, with its famous ruins and seasonal food pairings crafted by top chefs. Guests love the opportunity to stroll the grounds and enjoy the blend of history, architecture, and local wine. The experience is especially suited for travelers interested in combining history, architecture, and gourmet food with their wines.

Guests describe the guide as helpful and informative, adding to the overall memorable experience. At $235 per person, it offers a good mix of culinary adventure and wine tasting, especially for those who want a deeper cultural context.

Bottom Line: For lovers of wine, history, and food, this tour offers an engaging combination of sensory delights and cultural insights.

How to Choose the Right Charlottesville Wine Tour

When selecting a wine tour, consider your budget, preferred experience style, and group size. The private custom tours are best for those wanting maximum flexibility and personalized attention, though they come at a higher price. Meanwhile, the group tours or smaller private options provide excellent value and more guided structure.

Think about whether you want a luxury vehicle with panoramic views, or if you’re happy with a more intimate, straightforward experience. For those interested in combining wine with culinary experiences or historic sites, tours like the Wine and Culinary Delight are ideal.

Booking early is recommended, especially in peak seasons from spring to fall, when vineyard schedules fill up quickly. If you’re celebrating a special occasion or want exclusive access, the luxury private tour or custom private experience are your best bets.

Final Thoughts

Charlottesville offers a wide spectrum of wine touring options—from private, tailored days with luxury vehicles to more affordable, personalized group outings. If you’re seeking privacy and flexibility, the Virginia Private Custom Wine Tour tops the list. For small groups wanting to shape their own itinerary, the Private Charlottesville Area Wine Tour is an excellent choice. And for those looking to indulge in style and panoramic views, the luxury tour with a panoramic sunroof is hard to beat.

Whatever your style, booking your wine adventure early and choosing a tour that matches your interests will ensure a memorable day. Cheers to discovering Virginia’s wines and stories, one glass at a time.