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Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Morning

Start your day with a visit to Trump Winery , owned by former President Donald Trump's son, Eric. Take a tour of the vineyard and enjoy a wine tasting with stunning views of the Blue Ridge Mountains.

Afternoon

Head to Jefferson Vineyards , one of the oldest wineries in Virginia, for a tour and tasting of their award-winning wines. Afterward, take a stroll through Mulberry Row , a historic site at Thomas Jefferson's Monticello, where enslaved African Americans lived and worked.

Evening

Enjoy dinner and live music at Blenheim Vineyards , a boutique winery owned by musician Dave Matthews.

Bedtime

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Morning

Start your day with a brewery tour and tasting at Champion Brewing Company , known for their award-winning beers. Afterward, visit the University of Virginia , founded by Thomas Jefferson, and take a tour of the historic campus.

Afternoon

Enjoy a traditional Southern lunch at Michie Tavern , a historic inn and tavern that dates back to 1784. Afterward, take a scenic drive to Shenandoah National Park , where you can hike, bike, or drive along the famous Skyline Drive.

Evening

Relax with a beer and live music at Starr Hill Brewery , a popular craft brewery in Charlottesville.

Bedtime

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Morning

Start your day with a visit to Jefferson Vineyards , where you can enjoy a tour and tasting of their award-winning wines. Afterward, take a stroll through Mulberry Row , a historic site at Thomas Jefferson's Monticello, where enslaved African Americans lived and worked.

Afternoon

Head to Barboursville Vineyards , one of the oldest and most respected wineries in Virginia, for a tour and tasting of their premium wines. Afterward, visit the nearby ruins of the Barboursville mansion, designed by Thomas Jefferson.

Evening

Enjoy a beer and dinner at Wild Wolf Brewing Company , a popular brewery and restaurant in Nellysford.

Bedtime

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Morning

Start your day with a tour and tasting at Keswick Vineyards , a family-owned winery that produces high-quality Virginia wines. Afterward, take a scenic drive to the University of Virginia , founded by Thomas Jefferson.

Afternoon

Enjoy a traditional Southern lunch at Michie Tavern , a historic inn and tavern that dates back to 1784. Afterward, visit the Phipps Conservatory and Botanical Gardens , a beautiful indoor and outdoor garden that features a variety of plant species from around the world.

Evening

Enjoy dinner and live music at Hard Rock Café Pittsburgh , a popular restaurant and music venue in downtown Pittsburgh.

Bedtime

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Morning

Start your day with a ride on the Duquesne Incline , a historic cable car that offers stunning views of the Pittsburgh skyline. Afterward, visit the Cathedral of Learning , a towering Gothic Revival building that serves as the centerpiece of the University of Pittsburgh.

Afternoon

Take a scenic drive to Pittsburgh Mt. Washington , a neighborhood that offers panoramic views of the city skyline and the three rivers. Afterward, visit the Carnegie Science Center , a museum that features interactive exhibits on science, technology, and innovation.

Evening

Enjoy dinner and drinks at Pittsburgh Station Square , a historic riverfront complex that features a variety of restaurants, shops, and entertainment options.

Bedtime

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