Romantic Wine Tasting Weekend in Charlottesville

A renowned university. Presidential homes. A nearby national park. Charlottesville, Virginia has no shortage of entertainment for out of town visitors. However, you can spend an entire weekend focused on the bounty of the many vineyards surrounding the Charlottesville area. In the heart of Virginia among the Monticello Wine Trail you’ll find over 30 wineries, many with award winning wines, plus numerous charming inns & bed and breakfasts and excellent restaurants. To help you plan your wine tasting weekend in Charlottesville, here is our favorite itinerary.


  1. Make your arrival in Charlottesville on Friday evening and head straight to your accommodations at Boar’s Head Resort. Just outside of town you’ll find this historic and peaceful countryside resort with all the amenities you need for a restful and romantic wine tasting weekend. Check into your room, which is bright and modern with traditional touches and a historical reminder of the property’s roots all the way back to Thomas Jefferson.
  2. If you arrive early enough, make your way to the Friday evening wine reception from 5-6pm. All guests are welcome for a glass of wine on the house, possibly from a local winery.
  3. Unwind from your busy week by grabbing a casual bite to eat in the hotel’s bar, accompanied by one of their classic cocktails.
  4. Spend the remainder of the night stargazing from your personal patio or balcony, enjoying the sounds of the outdoors in the country.


  1. Start your morning getting refreshed in Boar’s Head Resort’s spa with a massage or the wine-themed Vino-Therapy Antioxidant Manicure and Pedicure. Or, get in some exercise at the top-ranked tennis or squash facilities, resort pools, or on the golf course.
  2. After your visit to the spa or athletic facilities, you will be famished! It’s time to grab breakfast at the Boar’s Head Resort’s dining room. Their expansive buffet includes almost any traditional breakfast food you can imagine. Fill up because there is a big day of wine tasting ahead!
  3. Drive 20 minutes to the first winery, Pollak Vineyards. When you arrive, you’ll drive through the middle of the vineyard to your way to the tasting room. The bright and airy tasting room is warm in the winter with a large stone fireplace and refreshing on warm days. The wine tasting line up provides many traditionally Virginian wines with a few special stand outs: Viognier, Meritage, Mille Fleur. After your tasting, take a glass of your favorite wine and spend some time admiring the mountain view on the patio or by the pond.
  4. Another 10 minutes down the road is Veritas Vineyards and Winery. Virginia is known for “Love” signs and you’ll be presented with a spectacular one made of corks hanging from the ceiling. Do a tasting, get another glass of your favorite, and make your way to the patio for a sandwich or cheese plate to enjoy while gazing over Veritas’ vineyards.
  5. Make your way north 15 minutes to King Family Vineyards for a winery tour. You’ll want to pick the 3pm tour, which lasts 1 hour and takes you on an extremely educational tour of one of the King Family’s vineyards, wine making facility, and barrel room. Following your tour, you’ll be treated to a tasting of King Family’s estate wines by your guide. What makes this experience special is that you learn and see what it takes for the grape to go from the vine to the crusher to the barrel to the bottle and finally your glass giving you a personal connection to the wine. Be sure to get a glass of Meritage, the 2018 Governor’s Cup winner, and wrap up your afternoon on the patio listening to the peace and quiet of the countryside.
  6. After freshening up for dinner, make your way to town for dinner at Public Fish & Oyster House. Alongside a wide selection of oysters and seafood you’ll find a varying and wonderful wine list with bottles from around the world.


  1. Wake up and head to Bodo’s Bagels for brunch. This local bagel chain has delicious homemade bagels and breakfast sandwiches that will be a good base for your second day of wine tasting.
  2. Jefferson Vineyards is the first stop on your agenda today. Named after America’s third president, the winery is just minutes away from Monticello. Take note of the winery’s award-winning Viognier. If you care to stay awhile, the winery offers hillside seating overlooking one of their vineyards.
  3. Travel 10 minutes down the country roads to Blenheim Vineyards. Owned by musician Dave Matthews and his family, Blenheim has spectacular views that you’ll adore during your tasting. Also, take a peek into the basement barrel room through the openings in the tasting room floor. You’ll taste several wines made using a blend of American, French, and Hungarian oak, the latter of which is unusual to the Virginia region. Choose to eat lunch here on the deck if a food truck is visiting or head to your last stop for lunch.
  4. Trump Winery has claimed to be the largest in Virginia. One look at the vineyards on the 1,300 acre estate and you’ll realize it’s true. At Trump you’ll find several sparkling wines, a great way to end your wine tasting weekend getaway. Enjoy a glass with lunch from Trump’s menu of delicious sandwiches and salads. Cheers to a fantastic weekend!