8 days in Charlottesville & Williamsburg Itinerary

8 days in Charlottesville & Williamsburg Itinerary

Created using Inspirock Virginia journey planner

Plan created by another user. Make it yours
1
Charlottesville
— 3 nights
2
Williamsburg
— 4 nights

S M T W T F S
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3
nights
Charlottesville

Charlottesville ©

Hoo-Ville

Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Satisfy your inner culture vulture at James Madison's Montpelier and Monticello. Give yourself a bit of retail therapy at King Family Vineyards and McGuffey Art Center. Get out of town with these interesting Charlottesville side-trips: Copper Fox Distillery (in Sperryville), Appomattox Court House National Historical Park (in Appomattox) and Skyline Drive (in Shenandoah National Park). And it doesn't end there: steep yourself in history at James Monroe's Highland, indulge your thirst for a good beer at Bold Rock Hard Cider, and brush up on your knowledge of spirits at River Hill Wine & Spirits.

To see ratings, traveler tips, other places to visit, and tourist information, refer to the Charlottesville online trip maker.

Chicago to Charlottesville is an approximately 4.5-hour flight. You can also drive; or take a train. You'll lose 1 hour traveling from Chicago to Charlottesville due to the time zone difference. Expect a daytime high around 80°F in September, and nighttime lows around 60°F. Finish your sightseeing early on the 11th (Wed) so you can drive to Williamsburg.

Things to do in Charlottesville

Historic Sites · Parks · Nature · Shopping

Side Trips

Highlights from your plan
Monticello ©
Monticello
James Madison's Montpelier ©
James Madison's Montpelier

4
nights
Williamsburg

Williamsburg ©

Colonial Capital

Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
Your cultural itinerary includes sights like Colonial Williamsburg and Williamsburg Art Gallery. Do your shopping at Carytown and R.P. Wallace & Sons General Store. You'll find plenty of places to visit near Williamsburg: Oak Crest Vineyard and Winery (in King George), Gauthier Vineyard (in Barhamsville) and Berkeley Plantation (in Charles City). Next up on the itinerary: explore the galleries of Historic Jamestowne, do a tasting at Williamsburg Winery, contemplate the long history of Bassett Hall, and take a tour of Jamestown Settlement.

For where to stay, other places to visit, maps, and tourist information, go to the Williamsburg online trip planner.

Traveling by car from Charlottesville to Williamsburg takes 2.5 hours. Alternatively, you can take a bus. Traveling from Charlottesville in September, you can expect nighttime temperatures to be somewhat warmer in Williamsburg, with lows of 66°F. Finish your sightseeing early on the 15th (Sun) so you can travel back home.

Things to do in Williamsburg

Historic Sites · Museums · Wineries · Shopping

Side Trips

Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Jamestown Settlement ©
Jamestown Settlement

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