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Charlottesville Itineraries

Planning a trip to Charlottesville? Our experienced travel editors break down the town so you can make the most of your stay. Let these itineraries be your guide, whether you're here for a weekend or a whole week.
  • Day 1
  • 1 Have breakfast at Bodo’s Bagels.
  • 2 Tour Monticello. Call ahead to reserve your tour time.
  • 3 Grab lunch at the historic Michie Tavern, Thomas Jefferson’s former watering hole.
  • 4 Take a walking tour of UVA, either with a guide or on your own, ending up at The Corner for happy hour at Mellow Mushroom.
  • 5 Walk or ride the free trolley to the Downtown Mall for a leisurely dinner at Hamiltons’ at First & Main.
  • Day 2
  • 1 Have brunch at the Bluegrass Grill & Bakery.
  • 2 Take a vineyard tour and wine tasting at the Barboursville Vineyards.
  • 3 See who’s playing and pick your favorite at one of Charlottesville’s goregeous and trendy downtown music venues, all located on the Downtown Mall.
  • 4 Have drinks and late night munchies at The X Lounge.
  • Day 3
  • 1 Head to Cafe Cubano for a light breakfast and some people watching on the Downtown Mall.
  • 2 Pick up the free weeklies, The C-ville Weekly and The Hook, to read about the latest in town while you relax on the mall. Be sure to check out the Free Speech Monument by the Pavilion, and add your own comments if the spirit moves you.
  • 3 Enjoy the lunch buffet at Himalayan Fusion, located on the mall.
  • 4 Take a light hike and/or play disc golf at Walnut Creek Park.
  • 5 Have dinner at Mas.
  • Day 4
  • 1 Pick up a section of the Rivanna Trail near UVA and walk around Charlottesville in the woods.
  • 2 Have lunch at Zazus Fresh Grille.
  • 3 Check the UVA sports schedule and look for a game either at Klöckner Stadium or Davenport Field. The baseball, soccer, and lacrosse teams are among the nation’s best, and Klockner and Davenport are great places to catch a game. 
  • 4 If it’s not the right season for sports, visit Ash Lawn-Highland for the afternoon.
  • 5 Happy Hour and Trivia Night at McGrady’s Irish Pub. Trivia is every Tuesday night. Get there early to secure a table!
  • Day 5
  • 1 Pick up some Spudnuts for breakfast, then take a day trip out to Jamestown Settlement and Colonial Williamsburg.
  • 2 Head back in town at night, mingle with laid back locals at South Street Brewery.
  • Day 6
  • 1 Pack a lunch and drive up to the Blue Ridge Parkway for a moderate hike at Humpback Rocks. You can have a picnic at the top of the mountain.
  • 2 Pick up a pie at Crozet Pizza on your way back into town. Call ahead, as the demand is surprisingly high at this little pizza joint. You’ll soon see why!
  • Day 7
  • 1 Have breakfast at The Villa Diner.
  • 2 Shop at Barracks Road Shopping Center—be sure to check out The Virginia Shop for souvenirs and gifts.
  • 3 Have lunch at Hotcakes.
  • 4 Head to the downtown Mall for Fridays After Five celebration.
  • 5 Grab dinner at Zocalo.


  • DAY 1
  • DAY 2
  • DAY 3
  • DAY 4
  • DAY 5
  • DAY 6
  • DAY 7