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.

Hazy Mountain Vineyards & Brewery

King Family Vineyards

  • Winery Tour & Tasting: A behind-the-scenes glimpse into the vineyard and winemaking programs. Available for groups of 2-12. Tours are not private unless all spots are booked by one party.
  • Founders Tasting: A seated, intimate tasting hosted in King Family's private library and led by one of the winery's founders. Available on Saturdays or by appointment.
  • Private Reserved Tasting: A pre-reserved offering in the indoor Pavilion with a King Family Associate. $100 or 4 guest minimum.

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 & 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 7 wines and a delicious picnic. The safari is offered seasonally, weather-permitting.

Michael Shaps Wineworks

  • Small Group Guided Private Tasting: Visit Michael Shap's Main Tasting Room (1650 Harris Creek Road) for a private tasting for groups of 6-20. 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 Tastings: A tasting of 6 wines led by a Valley Road Vinista. Comes with your own Valley Road wine glass. Must be booked ahead of time.

Specialty Experiences

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

Tipsy Wagen Tours Tipsy Wagen Tours is a fun and unique wine and beer tour company.We offer memorable and intimate tour experiences in the Charlottesville area. Each of our tours allows you to relax and enjoy a ride in our vintage VW Bus… Learn More
Crozet Trolley Transportation around Charlottesville, by trolley! Wine and beer tours, private charters for groups. Learn More
Cville Picnic C'ville Picnic is Charlottesville's premier luxury picnic experience. Specializing in romantic dates, proposals, anniversaries, brunch with the girls (or guys) and any event in between you'll want to book even if you've never picnicked in your life. Our attention to… 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
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
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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