Wine Tours & Experiences

Whether you're looking to book a private tasting, transportation to multiple wineries, or an experience that's completely unique, we have everything you need to plan the perfect wine getaway.

On-Site & Private Tours

These wineries offer regular guided tastings or private on-site tours. Many other wineries can accommodate small groups. Please call individual wineries ahead of time to see if they can offer a tour or tasting for your party.

Eastwood Farm and Winery

Guided Tastings: Led by a member of Eastwood's team, the guided tasting experience is a great chance to sample five or eight wines, learn a bit about the winemaking process, Virginia viticulture, and the winery. Both tastings offer a selection of Eastwood's white and red wines, including their gold medal winning wines. Available for groups of 1 - 20 or more. Advance reservations are required.

Hazy Mountain Vineyards & Brewery

  • Guided Tasting: Hazy Mountain Vineyards & Brewery offers a standard Guided Tasting with six of their most popular wines. No reservations needed and available during regular tasting rooms hours.
  • Private Guided Tasting: Available for groups of 10 or more with optional food menu. The experience includes a selection of six wines and exclusive use of the Private Tasting Room. Advance registration required.

King Family Vineyards

  • Guided Tasting: King Family's expert wine team will lead you through a personalized tasting of five wines of your choosing, offering insight and connection along the way. Reservations encouraged for groups of four or more.
  • Seated Tasting: A seated, intimate tasting with a selection of five wines from King Family's library collection. This experience is ideal for groups of two to six guests and requires an advance reservation.
  • Winery Tour and Tasting: A behind-the-scenes look at the winery's vineyard management and winemaking programs. Includes a a walk through the vines, a visit to the tank and barrel rooms, and guided tasting. Reservations required.

Merrie Mill Farm & Vineyard

  • Guided Tasting: An intimate tasting led by a Merrie Mill associate. You will be guided through each wine with detail in addition to enjoying a thoughtfully selected and paired cheese and charcuterie board. Reserve ahead of time.
  • Wine Tasting and Vineyard Safari: A one-of-a-kind tasting experience! Take a vintage safari Land Rover to tour the 12-acre vineyard before arriving at a safari-style tent for a guided tasting of eight wines and a delicious picnic. The safari is offered seasonally, weather-permitting.

Michael Shaps Wineworks

  • Small Group Guided Private Tasting: Visit Michael Shaps Winery for a private tasting for groups of 5 - 24. Click on "Make a Reservation" to book a time slot. Charcuterie can be arranged. Larger groups can also be accommodated for larger events.

Pippin Hill Farm & Vineyard

  • Vintner's Table: A 4-5 course meal of chef-inspired fare for parties of 10 or more. The perfect agritourism experience.
  • Estate Tour & Tasting: An in-depth exploration of Pippin Hill's wines, vines, and garden-to-table cuisine for parties of 2-8.
  • Group Reservations: Groups of 7+ are required to make advance reservations.

Valley Road Vineyards

  • Private Tasting: A tasting of six wines led by a Valley Road Vinista. Comes with your own Valley Road wine glass. Must be booked ahead of time.

Virginia Wine Collective

  • Guided Tasting and Tour: A guided tasting and behind-the-scenes glimpse into winemaking at Eastwood's new production facility, called the Virginia Wine Collective. Available for groups of two or more. Reserve in advance.

Specialty Experiences

If you're looking for a completely unique and memorable trip, get outside-the-box with one of these specialty experiences.

Blue Ridge Concierge Blue Ridge Concierge is a local and woman-owned luxury planning service for both visitors and locals in the Charlottesville and Central Virginia area. Whether you're staying in a vacation rental, hotel, or bed & breakfast—or you're a local looking to… Learn More
Crozet Trolley Transportation around Charlottesville, by trolley! Wine and beer tours, private charters for groups. Learn More
Indian Summer Guide Service We offer private, guided, horseback rides around several vineyards in the area. We are currently riding at Castle Hill Cider, Chisholm Vineyard, Cunningham Creek Winery, Glass House Winery, Keswick Vineyards, King Family Vineyards, Pollak Vineyards, and Veritas Vineyard & Winery… Learn More
James River Batteau Company James River Batteau Company offers one-of-a kind river experiences that get you out on the water in style! Take a step back in time, as you are invited aboard their 18th century replica James River Batteau for a River Tour… Learn More
Just Be Well Experience Welcome to the Just Be Well Experience. We’re a pop up luxury picnic service offering various styles of luxury picnics – from intimate gatherings, toddler picnics, solo picnics, friend gatherings, and more! Join us in our unique picnic services that… Learn More
Private Entourage Transportation Thank you for considering Private Entourage Transportation for your transportation needs. I am a veteran owned luxury car service that specifically caters to couples. I provide safe and fully chauffeured driving to venues of your selection. Whether it be wine… Learn More

Transportation & Tour Companies

Browse our local tour companies to book a day of transportation with multiple stops across the Monticello Wine Trail.

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