8 days in Virginia Itinerary

8 days in Virginia Itinerary

Created using Inspirock Virginia tour planner

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Route & dates

8 days in Virginia Itinerary

Start: New York City
Drive:  5​h 15​min
1
Chincoteague Island
— 1 night
Drive:  2​h 30​min
2
Virginia Beach
— 2 nights
Drive:  1​h 15​min
3
Williamsburg
— 2 nights
Drive:  2​h 15​min
4
Charlottesville
— 2 nights
Fly:  3​h 30​min
End: New York City

1
night
Chincoteague Island

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
For more things to do, reviews, where to stay, and more tourist information, read our Chincoteague Island road trip website .

New York City to Chincoteague Island is an approximately 5.5-hour car ride. You can also do a combination of train, flight, and taxi; or do a combination of train and bus. In June, daily temperatures in Chincoteague Island can reach 83°F, while at night they dip to 67°F. Finish your sightseeing early on the 2nd (Sat) to allow enough time to drive to Virginia Beach.

Things to do in Chincoteague Island

Outdoors Tours Wildlife
Highlights from your plan
Nature & Wildlife Tours

2
nights
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 2nd (Sat): explore the world behind art at Chrysler Museum of Art and then tour the pleasant surroundings at Sandbridge Beach. Get ready for a full day of sightseeing on the 3rd (Sun): admire the masterpieces at Virginia Museum of Contemporary Art, then brush up on your military savvy at Military Aviation Museum, and then stroll through Croatan Beach.

To see maps, photos, more things to do, and more tourist information, read our Virginia Beach itinerary planner .

You can drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. June in Virginia Beach sees daily highs of 84°F and lows of 68°F at night. Finish your sightseeing early on the 4th (Mon) to allow enough time to drive to Williamsburg.

Things to do in Virginia Beach

Beaches Outdoors Parks

Side Trip

Chrysler Museum of Art
Highlights from your plan
Sandbridge Beach ©
Sandbridge Beach
Military Aviation Museum ©
Military Aviation Museum
Chrysler Museum of Art ©
Chrysler Museum of Art

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.
Explore hidden gems such as American Revolution Museum at Yorktown and Hollywood Cemetery. Colonial Williamsburg and Bruton Parish Episcopal Church will appeal to history buffs. Explore the numerous day-trip ideas around Williamsburg: The Mariners' Museum & Park (in Newport News) and The American Civil War Museum - White House and Museum of the Confederacy (in Richmond). And it doesn't end there: browse the exhibits of Historic Jamestowne, stop by Yankee Candle Company, and explore the world behind art at Abby Aldrich Rockefeller Folk Art Museum.

For reviews, traveler tips, other places to visit, and tourist information, refer to the Williamsburg itinerary planner.

Getting from Virginia Beach to Williamsburg by car takes about 1.5 hours. Other options: take a bus. In June, plan for daily highs up to 88°F, and evening lows to 69°F. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Charlottesville.

Things to do in Williamsburg

Museums Historic Sites Parks

Side Trips

Richmond, The Mariners' Museum & Park, American Revolution Museum at Yorktown
Highlights from your plan
Hollywood Cemetery ©
Hollywood Cemetery

2
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.
Start off your visit on the 7th (Thu): contemplate the long history of Frontier Culture Museum, steep yourself in history at James Madison's Montpelier, and then learn about winemaking at Barboursville Vineyards and Historic Ruins. Here are some ideas for day two: admire the natural beauty at Thomas Jefferson's Monticello, then get a taste of the local shopping with Michie Tavern, then contemplate the long history of James Monroe's Highland, and finally gain insight at University of Virginia.

Planning Charlottesville trip won't be overwheling when you use's Insprock itinerary maker.

Getting from Williamsburg to Charlottesville by car takes about 2.5 hours. Other options: take a bus; or do a combination of train and bus. Traveling from Williamsburg in June, Charlottesville is little chillier at night with lows of 63°F. Finish your sightseeing early on the 8th (Fri) to allow enough time to travel back home.

Things to do in Charlottesville

Historic Sites Parks Nightlife

Side Trips

Frontier Culture Museum, James Madison's Montpelier, Barboursville Vineyards and Historic Ruins
Highlights from your plan
Frontier Culture Museum ©
Frontier Culture Museum
James Madison's Montpelier ©
James Madison's Montpelier
James Monroe's Highland ©
James Monroe's Highland

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