5 days in Virginia Itinerary

5 days in Virginia Itinerary

Created using Inspirock Virginia journey builder

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Route & dates

5 days in Virginia Itinerary

Start: Simpsonville
Drive:  7​h
1
Charlottesville
— Few hours
Drive:  2​h 15​min
2
Williamsburg
— 2 nights
Drive:  1​h 15​min
3
Virginia Beach
— 1 night
Drive:  8​h
End: Simpsonville

few
hours
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.
On the 18th (Thu), do a tasting at Keswick Vineyards, then contemplate the long history of Mulberry Row, and then take in nature's colorful creations at Thomas Jefferson's Monticello.

To find reviews, more things to do, where to stay, and tourist information, read Charlottesville trip builder tool .

Simpsonville to Charlottesville is an approximately 6-hour car ride. You can also fly. Expect slightly colder evenings in Charlottesville when traveling from Simpsonville in April, with lows around 46°F. Wrap up your sightseeing on the 18th (Thu) early enough to drive to Williamsburg.

Things to do in Charlottesville

Historic Sites Wineries Parks

Side Trip

Keswick Vineyards
Highlights from your plan
Monticello ©
Monticello
Keswick Vineyards ©
Keswick Vineyards

2
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.
Kick off your visit on the 19th (Fri): steep yourself in history at Colonial Williamsburg, witness the site of a historic battle at American Revolution Museum at Yorktown, and then pause for some serene contemplation at Bruton Parish Episcopal Church. Here are some ideas for day two: contemplate in the serene atmosphere at St. Luke's Historic Church & Museum, then see the interesting displays at The Mariners' Museum & Park, then explore the world behind art at Abby Aldrich Rockefeller Folk Art Museum, and finally admire the masterpieces at DeWitt Wallace Decorative Arts Museum.

For photos, where to stay, more things to do, and tourist information, use the Williamsburg trip planning site .

Drive from Charlottesville to Williamsburg in 2.5 hours. Alternatively, you can take a bus. In April in Williamsburg, expect temperatures between 73°F during the day and 50°F at night. Finish up your sightseeing early on the 20th (Sat) so you can go by car to Virginia Beach.

Things to do in Williamsburg

Museums Historic Sites Parks

Side Trips

The Mariners' Museum & Park, American Revolution Museum at Yorktown, St. Luke's Historic Church & Museum
Highlights from your plan
St. Luke's Historic Church & Museum ©
The Mariners' Museum & Park ©
The Mariners' Museum & Park

1
night
Virginia Beach

Virginia Beach ©
Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
Kick off your visit on the 21st (Sun): get engrossed in the history at Military Aviation Museum, stroll through Sandbridge Beach, and then take in the waterfront at Virginia Beach Boardwalk.

To see reviews, ratings, more things to do, and more tourist information, use the Virginia Beach online sightseeing planner .

Getting from Williamsburg to Virginia Beach by car takes about 1.5 hours. Other options: take a bus; or take a bus. April in Virginia Beach sees daily highs of 69°F and lows of 50°F at night. Wrap up your sightseeing on the 21st (Sun) early enough to travel back home.

Things to do in Virginia Beach

Museums Beaches Parks
Highlights from your plan
Military Aviation Museum ©
Military Aviation Museum
Sandbridge Beach ©
Sandbridge Beach
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk

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