8 days in Charlottesville & Williamsburg Itinerary

8 days in Charlottesville & Williamsburg Itinerary

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Route & dates

8 days in Charlottesville & Williamsburg Itinerary

Start: Chicago
Fly:  4​h
1
Charlottesville
— 3 nights
Drive:  2​h 15​min
2
Williamsburg
— 4 nights
+2
bus + taxi + Fly:  5​h 30​min
End: Chicago

3
nights
Charlottesville

Charlottesville ©
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.
For shopping fun, head to King Family Vineyards or McGuffey Art Center. Popular historic sites such as James Madison's Montpelier and James Monroe's Highland are in your itinerary. 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). There's much more to do: take in nature's colorful creations at Monticello, brush up on your knowledge of spirits at River Hill Wine & Spirits, and sample the tasty concoctions at Bold Rock Hard Cider.

To find out how to plan a trip to Charlottesville, use our trip itinerary maker.

Chicago to Charlottesville is an approximately 4-hour flight. You can also do a combination of flight and bus; or drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In September, daytime highs in Charlottesville are 80°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 11th (Wed) early enough to drive to Williamsburg.

Things to do in Charlottesville

Parks Historic Sites Nature

Side Trips

Skyline Drive, Appomattox Court House National Historical Park, River Hill Wine & Spirits, Copper Fox Distillery, King Family Vineyards
Highlights from your plan
Monticello ©
Monticello
James Madison's Montpelier ©
James Madison's Montpelier

4
nights
Williamsburg

Williamsburg ©
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.
Colonial Williamsburg and Williamsburg Art Gallery will appeal to museum buffs. Get some historical perspective at Bassett Hall and Historic Jamestowne. Explore Williamsburg's surroundings by going to Oak Crest Vineyard and Winery (in King George), Berkeley Plantation (in Charles City) and Gauthier Vineyard (in Barhamsville). And it doesn't end there: explore the world behind art at Abby Aldrich Rockefeller Folk Art Museum, do a tasting at Williamsburg Winery, look for gifts at R.P. Wallace & Sons General Store, and wander the streets of Carytown.

To find ratings, other places to visit, more things to do, and more tourist information, refer to the Williamsburg trip maker site .

You can drive from Charlottesville to Williamsburg in 2.5 hours. Alternatively, you can take a bus. Traveling from Charlottesville in September, plan for a bit warmer nights in Williamsburg, with lows around 66°F. Finish up your sightseeing early on the 15th (Sun) so you can travel back home.

Things to do in Williamsburg

Historic Sites Museums Wineries

Side Trips

Carytown, Oak Crest Vineyard and Winery, Gauthier Vineyard, Berkeley Plantation, Saude Creek Vineyards
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Jamestown Settlement ©
Jamestown Settlement

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