C'ville and Vino

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Nonprofit Cost: $4,480 + Add to Wishlist

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C'ville and Vino : Exclusive Winery Visits & Tastings, Behind-the-Scenes Monticello Tour, 3-Night Stay for 2 (8017-2n)

 The experience for 2 would include the following: 

  • 3-night stay in historic Bed & Breakfast
  • Wisdom Oak Winery visit & tasting with the winemaker
  • Stinson Vineyards visit & tasting with the winemaker
  • Behind-the-Scenes Day Pass at Monticello
  • Local guide available for experience recommendations
  • Winspire Booking and Concierge Service

Wineries, outdoor recreation, history, and farm-to-table dining await! Sip your new favorite vino at one of the 40+ wineries located along the Monticello Wine Trail, or enjoy the refreshing breeze on one of the area's scenic hiking trails, then grab a bite to eat at one of the many restaurants with patio dining on the historic pedestrian Downtown Mall. Charlottesville and Albemarle County are home to world-renowned historic sites, including the homes of three of the country's founding fathers. 

Downtown Charlottesville

A visit to Charlottesville isn't complete without a stop at the Downtown Mall. It is one of the most beautiful and successful pedestrian malls in the nation, and it's located in historic downtown Charlottesville. A wonderful mix of restored and renovated buildings that typified small "downtowns" throughout the country can now be seen by visitors as they enjoy shopping, dining, and visiting along the brick-paved pedestrian area. Enjoy a 3-night stay in a historic Bed & Breakfast located minutes away.

 Wisdom Oak Winery

Wisdom Oak Winery is a family-owned and operated winery located in North Garden, Virginia. Located just minutes from Charlottesville, UVA, and right in the heart of the Monticello Wine Trail. Your experience will include an exclusive visit and tasting with the winemakers. 

 Stinson Vineyards

Stinson Vineyards is a family and winemaker-owned estate winery in Virginia’s Blue Ridge Mountains specializing in small-lot wines with a distinct French influence. The wines of Stinson Vineyards are enjoying growing critical acclaim, and the winery near Charlottesville has become a visitor destination for its fine wines, stunning views, and excellent hospitality. Enjoy a visit with the winemakers, a tasting, and take in the view at this gorgeous vineyard.


Visiting Thomas Jefferson’s house and the Monticello grounds engages the senses and stimulates the mind. Included is a Behind-the-Scenes Day Pass that allows you to explore the second and third floors, including the iconic Dome Room. The Behind-the-Scenes tour provides a fuller picture of life at Monticello and a better understanding of the complex world surrounding the man who authored the Declaration of Independence.

 Charlottesville Local Guide

A local guide will be available to assist with making recommendations for meals, drinks, other wineries, hikes, UVA Tours, and more. 

Winspire Booking & Concierge Service

Winspire provides a team of seasoned travel professionals who will help you redeem your experience. All travel-related details and reservations are handled for every part of your Winspire experience. Operating as a full-service travel agency, Winspire can assist with extra hotel nights, airfare, and additional guests. This service also provides you with an established network of onsite contacts who can help you book additional experiences, activities, and tours.


Travel must be completed within two years from the date of purchase. Reservations are subject to availability and must be booked a minimum of 60 days before travel. Ground transportation is the responsibility of the winner unless otherwise stated. Certificates cannot be replaced if lost, stolen, or destroyed. Purchases through charity fundraisers are non-refundable and packages cannot be resold.

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