Within every Virginia vacation lies an opportunity to pair outdoor adventures, historic sites, beaches, or mountains with locally sourced cuisine, hand crafted beverages, or a glass of fine Virginia wine. We like the sound of a little history and a few wineries for a well-rounded Virginia vacation. Discover the complete history of Virginia: The Birthplace of American Wine and read on to see how you can experience a perfect pairing of wine and history just about anywhere in Virginia.  


Williamsburg Winery Williamsburg Winery is one of the few wineries in coastal Virginia and is uniquely situated inside Virginia’s Historic Triangle. Just minutes north of Jamestown, the site of the first permanent English settlement in North America, Williamsburg Winery sits on the same land where colonists attempted winemaking nearly 400 years ago. These attempts by colonial cultivators were required by Acte 12 of 1619.** Although the colonists were unsuccessful in producing great vino, the winery harvests a signature Acte 12 Chardonnay made of 100% Virginia grapes as a tribute to its unique history. Don’t Miss: Tasting of Acte 12 Chardonnay at Williamsburg Winery. For Wine Lovers: Continue your Virginia Wine adventure at nearby wineries on the Colonial Wine Trail between Williamsburg and Richmond. Upper Shirley Vineyards neighbors Shirley Plantation and offers breathtaking views of the James River from its beautiful low country style setting. For History Lovers: Visit the Historic Triangle including Jamestown Settlement, Colonial Williamsburg, and the new American Revolution Museum at Yorktown. Governor's Palace at Colonial Williamsburg Where to Stay: Wedmore Place at Williamsburg Winery offers unique European inspired rooms. Other great options in nearby Colonial Williamsburg include quaint Colonial Houses, a comfortable Williamsburg Lodge, the 5-star Williamsburg Inn, and many more. Where to Eat: Wine and Brine Lounge at Williamsburg Winery is open every Saturday and Sunday between March and November and showcases a different Virginia oyster company and waterman each week. Other unique dining experiences include Kings Arms Tavern and Chowning’s Tavern in Colonial Williamsburg.  


Barboursville Vineyards Virginia entered the modern-era of winemaking when Barboursville Vineyards opened in 1976, having successfully planted and established the European vinifera vine on Virginia soil. The vineyard is located just outside of Charlottesville near Monticello, the home of Thomas Jefferson, where he attempted and failed to plant the same vines over two centuries ago. Owner Gianni Zonin, the head of one of Italy’s oldest wine families, set out fulfill Jefferson's dream by making fine wine in Virginia. He found great success and has since set the standard for a region now populated with more than 300 wineries. Don’t Miss: A tasting of Octagon, Barboursville Vineyard’s signature Bordeaux blend representing the highest expression of the estate’s European derivation and inspiration. For History Lovers: Include a Monticello Garden and Grounds Tour to explore Jefferson’s lifelong interest in gardening, botany and agriculture. Walk the grounds of Jefferson’s University of Virginia. University of Virginia For Wine Lovers: Explore the Monticello Wine Trail with over 30 wineries scattered throughout Virginia’s bucolic countryside with picturesque views of the Blue Ridge Mountains.
  • Gabriele Rausse Winery: For a unique and rather exceptional wine experience, visit Gabriele Rausse Winery to taste wines crafted by the “Father of Virginia Wine” himself. Gabriele Rausse was the pioneering winemaker at Barboursville Vineyards. Note: the tasting room is exclusively open Thursday, Friday and Sunday.
  • Horton Vineyards: Horton Vineyards is another one of Virginia’s oldest wineries and an industry pioneer for introducing varietal grapes that thrive in Virginia’s climate. Viognier was first planted by owner, Dennis Horton, and is now widely considered the state grape of Virginia. Horton is also known for reintroducing the Norton varietal, pioneered by Dr. Daniel Norton in Richmond in the 1800s. The tasting room is open daily; don’t miss a chance to try the award winning Horton 2015 Viognier.
  • Keswick Vineyards: For an enchanting wine experience, visit Keswick Vineyards at historic Edgewood Estate. The vineyard sits on the land of two important historical events, one during the Revolutionary War and the other during the Civil War. Include a walking vineyard tour with the winemaker himself!
The 1804 Inn at Barboursville Vineyards Where to Stay: The 1804 Inn and surrounding cottages at Barboursville Vineyards offer well-appointed suites with views of the vineyard and the Blue Ridge Mountains. Nearby accommodations include The Graduate Hotel or The Oakhurst Inn in the heart of Charlottesville. Where to Eat: Barboursville’s Palladio offers an elegant gastronomic experience including locally sourced Virginia fare through a Northern Italian perspective. Other favorites in the area include The Local and The Ivy Inn, to name a few of Charlottesville’s many farm-to-table restaurants.  


Philip Carter Winery of Virginia The Carter family name carries a 250-year legacy as producers of the first internationally recognized wines in America. Charles Carter, son of the infamous Robert “King” Carter, began growing grapes at his Cleve Plantation in King George County. In 1762, he sent a dozen bottles to England and was awarded a gold medal by the London Society for being the first to make a “spirited attempt towards the accomplishment of their views, respecting wine in America.” Today Philip Carter Strother is carrying on his family’s winemaking legacy as owner of Philip Carter Winery in Fauquier County. Philip Carter Winery has earned many awards for their wines, many of which are named for historic landmarks in Virginia. Don’t Miss: A tasting of 2015 Oatlands Norton in the Cleve Hall tasting room or a special educational experience of Wine History in Virginia including a full tasting and pairing with Virginia cheese at Philip Carter Winery. For History Lovers: Explore a 200-year-old gristmill in Aldie Mill Historic Park. Visit Oatlands Historic House and Gardens, a stately mansion with over 200 years of American history and culture. Or visit the beautiful Long Branch Plantation, built by another descendent of the Carter Family in 1811. Oatlands Plantation For Wine Lovers: Choose from 26 great wineries on the Fauquier Country Wine Trail including:
  • RdV Vineyards Bordeaux grapes planted on a rocky Virginia hillside are making Jefferson’s dream a reality, producing world-class wines that marry the elegance of Bordeaux with the bold spirit of California.
  • Boxwood Winery also crafts beautifully blended Bordeaux-style wines and sits on a National Historic Landmark. Boxwood Estate was one of the earliest established farms in Virginia and is located in the historic village of Middleburg.
  • Morais Vineyards & Winery brings their own family history of winemaking and heritage to Virginia by offering Portuguese inspired wines in an equally inspired setting, which even features a special LOVEwork for a fun photo opportunity!
Where to Stay: The Inn at Vineyards Crossing offers an intimate retreat located minutes from the wineries mentioned above. Stay at the Salamander Resort & Spa in Middleburg for a luxurious experience in the heart of Virginia’s horse country and foothills of the Blue Ridge Mountains. Airlie, set on 300 acres of verdant Virginia landscape, offers warm and welcoming accommodations with plenty of activities for everyone to enjoy, and a LOVEwork too! Salamander Resort & Spa Where to Eat: Farm-to-Table fare is accustomed to this area of Virginia, starting 38 years ago at one of America’s finest restaurants the Inn at Little Washington. More locally-sourced options include Field and Main Restaurant in Marshall and Harriman’s Virginia Piedmont Grill at the Salamander Resort.   We also recommend these related Virginia Wine Tours:
  • Fruits & Root's Monticello Wine Trail Tour perfectly pairs wine and history on a journey from Virginia Beach to the Monticello Wine Trail for all inclusive day filled with wine, food, shopping and fun as you bring history to life!
  • Monticello Appellation Wine Tours offers three different wine tours around the Charlottesville area and is listed as one of the top Wine Tours in the area.
  • Wish Wish Virginia Wine Tours offers wine and beer tours all over Virginia including Richmond, Williamsburg, the Northern Neck, Charlottesville, and Northern Virginia.