Discover Charlottesville’s top five wineries on a private tour. Enjoy scenic hills, historic attractions, and exceptional wines. Perfect for a fun, easy road trip.
Discover Charlottesville’s top five wineries on a private tour. Enjoy scenic hills, historic attractions, and exceptional wines. Perfect for a fun, easy road trip.
- Early Mountain Vineyards - Once owned by Revolutionary War veteran Lieutenant Joseph Early, who served under General George Washington at Valley Forge, Early Mountain Vineyards spans the base of the Blue Ridge Mountains and produces classic Bordeaux-style varietals like Cabernet Franc and Merlot. The expansive tasting room, voted #1 in America by…
- Early Mountain Vineyards - Once owned by Revolutionary War veteran Lieutenant Joseph Early, who served under General George Washington at Valley Forge, Early Mountain Vineyards spans the base of the Blue Ridge Mountains and produces classic Bordeaux-style varietals like Cabernet Franc and Merlot. The expansive tasting room, voted #1 in America by USA Today, offers both high-end dining and casual lounging for sampling wines from Early Mountain and other vineyards throughout Virginia. As a premier wedding venue, Early Mountain can transform a dream party into a beautiful reality. After all, Virginia is for lovers.
- King Family Vineyards - Nestled at the foothills of the Blue Ridge Mountains, King Family Vineyards is family-owned and operated. The winery specializes in luxurious wines that showcase the exceptional quality and terroir of the Monticello AVA. Starting with carefully selected estate grapes, winemaker Matthieu Finot crafts wines inspired by old-world offerings that also express Virginia’s character, such as Viognier, a staple of the state’s white wine selection. This summer, tasting room visitors are invited to join fieldside to watch polo every Sunday from Memorial Day weekend to mid-October. Gates at Roseland Polo open at 10 a.m. for tailgating or picnicking before the match begins at 1 p.m. In fact, after founders David and Ellen King moved to Virginia from Houston in 1995, their search for a farm had one requirement: twelve acres of relatively flat ground for a polo field. The idea of wine came later.
- Stinson Vineyards - Winemaking is a family affair at Stinson Vineyards. The estate winery in Virginia’s Blue Ridge Mountains is led by father-daughter duo Scott Stinson and Rachel Stinson Vrooman, along with Rachel’s husband Nathan. They draw inspiration from “garagiste” wineries of France in both their winemaking methods and the winery itself, which is built into an old three-car garage. The small-lot wines carry a distinct French influence, mainly from the Bordeaux and Loire Valley regions, emphasizing subtlety rather than ripeness. Visitors can shop the tasting room, which also doubles as a local farm store selling grass-fed beef, farm-raised pork and chicken, free-range organic eggs, and garden-fresh herbs. Inquire about an overnight stay at Stinson’s historic inn nestled among the vines, or at The Townsman, a boutique hotel on Charlottesville’s Downtown Mall. The Stinson family owns several accommodations to help customize your summer travel plans.
- Veritas Vineyard & Winery - In 1999, founders Andrew and Patricia Hodson planted five acres of grapes as a passion project. Today, Veritas spans more than 50 acres of vineyards and produces classic Old World wines using modern technology to capture varietal and regional character—from its barrel-fermented Chardonnay to its award-winning seasonal Flying Fox sweet vermouth.
- Pippin Hill Farm & Vineyards - Pippin Hill Farm & Vineyards stands out among the fine wineries in the Charlottesville wine region. It is a culinary vineyard that not only produces distinguished wines but also pairs them with artisan cuisine from an on-site farm. The six-acre vineyard is situated on a southern-facing hillside, rich with soil and a climate suited for varietals such as Sauvignon Blanc and Petit Verdot. Both the vineyard and surrounding gardens are part of Bundoran Farm, a sustainable community dedicated to Virginia’s countryside. Pippin Hill encourages guests to explore the gentle grounds and enjoy the health and beauty of the state.

- Private transportation
- Driver guide
- Mercedes Sprinter Minivan (Up to 14 passengers)
- Reservations to vineyards and wineries
- Reading materials
- Private transportation
- Driver guide
- Mercedes Sprinter Minivan (Up to 14 passengers)
- Reservations to vineyards and wineries
- Reading materials
- Lunch
- Dinner
- Gratuities
- Alcoholic beverages
- Lunch
- Dinner
- Gratuities
- Alcoholic beverages
Charlottesville, Virginia, boasts some of the nation’s most cherished historical landmarks and offers stunning vistas across the Shenandoah Valley. Experience a 6-hour guided tour to explore five of the most popular vineyards and wineries in Virginia’s historic wine country.
This tour can be tailored to suit your group’s preferences.
Tours extending…
Charlottesville, Virginia, boasts some of the nation’s most cherished historical landmarks and offers stunning vistas across the Shenandoah Valley. Experience a 6-hour guided tour to explore five of the most popular vineyards and wineries in Virginia’s historic wine country.
This tour can be tailored to suit your group’s preferences.
Tours extending beyond 6 hours will incur a charge of $125 for each additional hour.
- Alcoholic beverages are available for purchase by guest travelers 21+ years old.
- Guest travelers under 21 years old can only purchase non-alcoholic beverages.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.