Charlottesville isn’t just famous for Thomas Jefferson and Monticello—its wine scene is equally compelling. Surrounded by the Blue Ridge Mountains, this region offers a mix of scenic vineyards, historic estates, and intimate tasting experiences. Among the options, the Virginia Private Custom Wine Tour stands out for its personalized approach, letting you pick your stops and enjoy a picnic amid Virginia’s rolling hills. We love how this tour combines the beauty of the outdoors with the luxury of a private guide, making for a relaxed, distraction-free day.
While some tours focus on a specific area or historic sites, others offer tailored experiences based on your preferences. Whether you’re a wine newbie or a seasoned connoisseur, Charlottesville’s wine tours deliver a range of options from private outings to group adventures. Here’s a quick overview before diving into the details.
1. Virginia Private Custom Wine Tour from Charlottesville
This private custom tour is a standout for travelers who want flexibility. It typically lasts around five hours and includes visits to 3–4 wineries, with the option to choose your preferred tasting rooms. Your personal chauffeur will take you through the scenic Blue Ridge Mountains and Charlottesville’s countryside, making this perfect for a small group or couple wanting a bespoke experience.
What makes this tour truly special is the freedom to select wineries and enjoy a picnic lunch wherever you prefer, whether among the vines or in a scenic spot. The tour includes a knowledgeable guide, free bottled water, and the chance to sample Virginia wines in a relaxed setting. Reviewers consistently praise the personal touch and comfort—one callout is the guide Gillie, who’s described as “full of Southern charm” and “prompt and personable.”
This tour is excellent for those seeking a tailored, stress-free day with top-notch service. The value for the price—$499 for up to three people—reflects its private, customizable nature. Ideal for celebrating a special occasion or simply enjoying Virginia’s wine country at your pace.
Bottom line: A perfect pick for couples or small groups wanting a personalized, comfortable experience that highlights Virginia’s scenic beauty and wine diversity.
2. Private Charlottesville Area Wine Tour
For around $235 per person, the Private Charlottesville Area Wine Tour offers a more intimate, guided experience of the Monticello Wine Region. Lasting about five hours, it’s an ideal choice if you prefer a curated visit to some of the area’s standout vineyards like Merrie Mill Farm and the historic Barboursville Vineyards.
The tour’s flexibility is a major selling point—your guide can recommend lesser-known spots or visit your favorites. Guests have enjoyed the personable approach, with reviews mentioning “amazing recommendations” and “great conversations.” The itinerary often includes tasting at Merrie Mill Farm & Vineyard, known for its warm hospitality, and the renowned Barboursville, famous for its historic ruins and seasonal culinary pairings.
What sets this apart is the ability to customize your stops, making it perfect for wine enthusiasts eager for a more personal exploration. The tour provides a chance to learn about Virginia’s wine history while enjoying the scenery and wines.
Bottom line: This is a good choice if you value flexibility and expert guidance, especially for a small group interested in making personalized stops.
3. Custom Wine Tour In Black Suburban With Panoramic Sunroof
If you’re after a luxurious experience, the Custom Wine Tour in a Black Suburban offers just that. Priced at $549 for up to six people, this tour lasts about five hours and includes a fully customized itinerary, often visiting top vineyards like King Family and Pollak.
What makes this tour unique is the vehicle itself—a sleek, black SUV with a panoramic sunroof—adding a touch of elegance to your day. The guide will help craft your route based on your preferences, and you can expect visits to 3–4 wineries, with options for tastings, dining, or exploring historic ruins.
Guests appreciate the professional, clean fleet and the tailored experience, which can include winery history, food pairings, or sightseeing stops. Reviewers have noted the tour’s flexibility and the guide’s knowledge about local landmarks.
Bottom line: Ideal for travelers wanting a high-end, customized experience with a small group, emphasizing comfort and exclusivity.
4. Private Wine Tours (Minimum 3 & Maximum 6) Pickup Maximum 30 Mi
At number four, the Private Wine Tours for groups up to six are perfect for small groups seeking a guided day in Virginia’s wine country. For $85 per person, it covers about five hours of touring, with custom itineraries based on your preferences.
The main advantage is the personalized planning—your guide can include visits to iconic vineyards like Monticello or lesser-known hidden gems. Reviews praise the driver’s friendliness and flexibility, with one noting the ease of having all transport logistics handled while they enjoyed tastings and conversations. The tour also includes guided vineyard tours and the option to purchase wines.
This tour is a solid value, especially for groups who want the convenience of door-to-door service without sacrificing control over destinations. It’s suited for wine newcomers and seasoned aficionados alike.
Bottom line: Best for small groups eager for a flexible, guided experience without breaking the bank.
5. Wine and Culinary Delight Private Tour
For those who want to combine wine with excellent food, the Wine and Culinary Delight Private Tour is a top choice. Priced at $235 per person, this five-hour outing visits Barboursville Vineyards, famed for its historic ruins and seasonal culinary pairings, and Early Mountain Vineyards, known for crafting wines that highlight Virginia’s land.
What makes this tour special is the focus on sensory experiences—sampling wines while enjoying picturesque outdoor spaces and exploring Thomas Jefferson’s estate ruins. Guests love the mix of historical ambiance and high-quality wines, with reviews highlighting attentive guides and memorable tastings.
Ideal for travelers who want a mix of history, architecture, and wine, this tour balances education and indulgence. The inclusion of food and the scenic settings makes it a well-rounded experience.
Bottom line: Perfect for those wanting a taste of Virginia’s wine, history, and cuisine in one relaxed day.
6. 5 Hour Historic Thomas Jefferson Wine Tour
The Historic Thomas Jefferson Wine Tour combines wine tasting with a journey through Jefferson’s Virginia. For $247.50 per person, the five-hour tour includes visits to Jefferson Vineyards, the original site of Jefferson and Philip Mazzei’s winemaking efforts, plus a stop at the historic Barboursville ruins.
What makes this tour appealing are the stops that blend history with wine, including a self-guided walk around the Rotunda and a guided tasting at Jefferson Vineyards. The guide points out significant landmarks like the Exchange Hotel, giving a well-rounded experience of the area’s past and present.
Guests appreciate the mix of relaxed tastings and educational commentary. Reviewers note the personable guide and the chance to see Jefferson’s influence in the region.
Bottom line: A good choice for history buffs who want to combine wine tasting with a cultural tour of Charlottesville.
7. Family Wine Tour
Traveling with family? The Family Wine Tour offers private round-trip transfer from Pantops Shopping Center and is designed for ease. For $85 per person, it provides a flexible schedule with free time at your preferred destination, whether wineries, parks, or other sites.
What makes this appealing is the simplicity—no need to worry about driving or planning multiple stops. It’s ideal for families wanting a laid-back day with transportation sorted in advance. Reviews, though limited, mention the friendly driver and the convenience of having a dedicated service.
This tour is best suited for families or groups who value ease and flexibility without the focus solely on wine.
Bottom line: A practical choice for families seeking a relaxed outing with private transport and customizable stops.
$85.00 per person
8. Private Wine Tour for groups up to 6
Finally, the Private Wine Tour for groups up to six offers a curated experience for up to six guests. For $500 per group, this five-hour tour covers the Monticello Wine Trail, Nelson 151, and includes stops at three of your preferred wineries, breweries, or distilleries.
The flexibility to choose the venues lets your group explore your favorites or try something new. Guests appreciate the smooth booking process and the personalized attention, with the guide helping with reservations and suggestions. It’s an excellent choice for those who want a private, inclusive experience, tailored to their tastes.
Bottom line: Great for small groups or families wanting control over their wine and beverage stops, with a personalized touch.
$500.00 per group (up to 6)
How to Choose the Best Charlottesville Wine Tour
Consider your budget, group size, and interests. If privacy and customization matter most, options like the Virginia Private Custom Wine Tour or the Black Suburban Tour will suit you. For a family-friendly, low-stress experience, the Family Wine Tour offers easy transportation.
If you’re eager to blend history with wine, the Thomas Jefferson Tour is ideal. Budget travelers will find good value in the private group tours at $85 per person.
Booking early is recommended, especially during peak season in spring and fall, when vineyard events and festivals attract more visitors.
Final Thoughts
From luxurious private experiences to flexible group tours, Charlottesville offers a wide selection of wine adventures. Couples seeking an intimate escape may prefer the private custom tours, while groups or families benefit from guided transport options. History enthusiasts will enjoy tours blending Virginia’s past with its vineyards, and budget travelers can find great value in shared guided outings.
No matter your style, these tours promise a memorable day among Virginia’s scenic vines. Book early, plan your favorites, and enjoy a day of excellent wine and good company in Charlottesville’s beautiful landscape.