Charlottesville Adventure 5 Days Itinerary

Begin your day with a visit to the iconic University of Virginia. Founded by Thomas Jefferson, this UNESCO World Heritage site boasts stunning architecture and beautiful gardens. Take a guided tour to learn about its history and significance. Grab breakfast at Bodo's Bagels, famous for their freshly baked bagels and delicious spreads.

Next, make your way to Trump Winery for another delightful wine tasting experience. The winery offers breathtaking views of the Blue Ridge Mountains along with award-winning wines. Enjoy a leisurely lunch at Trump Winery's Tasting Room, where you can pair your meal with their exquisite wines.

Conclude your day with dinner at The Local, a restaurant that focuses on locally sourced ingredients to create mouthwatering dishes. After dinner, take a stroll around Downtown Mall to explore shops and cafes or catch some live music at one of the nearby venues.

Embark on an exciting outdoor adventure with the Shenandoah Valley: Fly Fishing Trip Full Day with Lunch. Spend your morning fly fishing in some of Virginia's most scenic rivers under the guidance of experienced instructors. Enjoy a packed lunch provided during the trip.

After returning from your fishing trip, visit Blenheim Vineyards, owned by musician Dave Matthews. The vineyard offers tastings in a relaxed setting with beautiful views of the vineyards. For lunch after fishing (if you're still hungry), try out Maya Restaurant which serves Southern-inspired cuisine.

End your day at Mulberry Row, part of Thomas Jefferson's Monticello estate. Explore this historic site that was once home to enslaved workers who lived and worked there during Jefferson's time. For dinner, dine at C&O Restaurant, known for its elegant atmosphere and gourmet dishes.

Start your day with a visit to the Champion Brewing Company. Known for its innovative craft beers, this brewery offers a variety of unique brews that are sure to please any beer enthusiast. Enjoy a tasting session and learn about the brewing process from the knowledgeable staff. For breakfast, head to Bluegrass Grill & Bakery, where you can enjoy hearty dishes like biscuits and gravy or their famous breakfast burritos.

After your brewery visit, make your way to the historic Mulberry Row at Monticello. This area was once home to enslaved workers who lived and worked on Thomas Jefferson's estate. Take a guided tour to learn about their lives and contributions. For lunch, stop by The Whiskey Jar, a Southern eatery known for its comfort food and extensive whiskey selection.

In the evening, explore more of Charlottesville's vibrant downtown area. Visit the Downtown Mall, one of the longest pedestrian malls in the country, where you can shop at local boutiques or enjoy street performances. For dinner, dine at Zocalo, a popular restaurant offering contemporary Latin American cuisine.

Blenheim Vineyards awaits you for another delightful wine tasting experience. Owned by musician Dave Matthews, this vineyard offers tastings in a relaxed setting with beautiful views of the vineyards. Enjoy a light breakfast at Para Coffee, known for its excellent coffee and pastries.

Trump Winery is your next stop for an afternoon of wine tasting amidst breathtaking views of the Blue Ridge Mountains along with award-winning wines. Enjoy lunch at Trump Winery's Tasting Room, where you can pair your meal with their exquisite wines.

Michie Tavern is an ideal spot to conclude your Charlottesville adventure with its historic charm and traditional Southern fare. Dine at their tavern restaurant which serves hearty colonial-style meals in an 18th-century setting.