11 days in Virginia Itinerary

11 days in Virginia Itinerary

Created using Inspirock Virginia trip itinerary planner

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Route & dates

11 days in Virginia Itinerary

Start: Chicago
Fly:  3 h 30 min
1
Arlington
— 1 night
Drive:  3 h 45 min
2
Chincoteague Island
— 2 nights
Drive:  2 h 30 min
3
Virginia Beach
— 3 nights
Drive:  1 h 15 min
4
Williamsburg
— 3 nights
Drive:  2 h 15 min
5
Charlottesville
— 1 night
Fly:  4 h
End: Chicago

1
night
Arlington

Arlington ©
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
On the 13th (Thu), pause for some serene contemplation at Our Lady Queen of Peace Catholic Church and then stroll the grounds of Arlington National Cemetery. Get ready for a full day of sightseeing on the next day: see the interesting displays at Steven F. Udvar-Hazy Center, take in the exciting artwork at Torpedo Factory Art Center, then steep yourself in history at Old Town, and finally get to know the fascinating history of Tomb of the Unknowns.

For more things to do, photos, other places to visit, and more tourist information, you can read our Arlington tour itinerary planner .

Chicago to Arlington is an approximately 3.5-hour flight. You can also do a combination of flight, bus, and subway; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Arlington. Expect somewhat warmer evenings in Arlington when traveling from Chicago in June, with lows around 69°F. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Chincoteague Island.

Things to do in Arlington

Historic Sites Museums Neighborhoods

Side Trips

Alexandria, Steven F. Udvar-Hazy Center
Highlights from your plan
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Arlington National Cemetery ©
Arlington National Cemetery
Steven F. Udvar-Hazy Center ©
Steven F. Udvar-Hazy Center

2
nights
Chincoteague Island

Chincoteague Island ©
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Start off your visit on the 15th (Sat): identify plant and animal life at Chincoteague National Wildlife Refuge. Keep things going the next day: cast your line with a fishing tour and then surround yourself with nature on a nature and wildlife tour.

For where to stay, ratings, reviews, and tourist information, use the Chincoteague Island travel tool .

Drive from Arlington to Chincoteague Island in 4 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus and taxi. Expect a daytime high around 82°F in June, and nighttime lows around 66°F. Wrap up your sightseeing on the 16th (Sun) early enough to drive to Virginia Beach.

Things to do in Chincoteague Island

Wildlife Parks Nature
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Fishing Charters & Tours

3
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.
You'll explore and learn at Virginia Aquarium & Marine Science Center and Chrysler Museum of Art. You'll enjoy a bit of beach vacationing at Virginia Beach and Cape Charles Beach. There's still lots to do: kick back and relax at Sandbridge Beach, brush up on your military savvy at Military Aviation Museum, play a few rounds at Jungle Golf, and take in the waterfront at Virginia Beach Boardwalk.

To see other places to visit, maps, traveler tips, and other tourist information, use the Virginia Beach trip 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. In June in Virginia Beach, expect temperatures between 85°F during the day and 69°F at night. Finish up your sightseeing early on the 19th (Wed) so you can go by car to Williamsburg.

Things to do in Virginia Beach

Parks Outdoors Beaches

Side Trips

Cape Charles Beach, Chrysler Museum of Art
Highlights from your plan
Virginia Beach ©
Virginia Beach
Military Aviation Museum ©
Military Aviation Museum
Sandbridge Beach ©
Sandbridge Beach

3
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.
Get a sense of the local culture at Colonial Williamsburg and Governor's Palace. Your inner history buff will appreciate Historic Jamestowne and Jamestown Settlement. Plan for a day of cool, family-friendly fun on the 21st (Fri) at Busch Gardens Williamsburg. It doesn't end there: learn about winemaking at Williamsburg Winery and explore the world behind art at Abby Aldrich Rockefeller Folk Art Museum.

To find other places to visit, where to stay, photos, and more tourist information, you can read our Williamsburg trip planner .

Traveling by car from Virginia Beach to Williamsburg takes 1.5 hours. Alternatively, you can take a bus; or take a bus. In June in Williamsburg, expect temperatures between 87°F during the day and 68°F at night. Wrap up your sightseeing on the 22nd (Sat) to allow time to drive to Charlottesville.

Things to do in Williamsburg

Historic Sites Museums Theme Parks
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg

1
night
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 23rd (Sun): indulge your taste buds at King Family Vineyards, learn about winemaking at Jefferson Vineyards, and then contemplate the long history of Thomas Jefferson's Monticello.

For other places to visit, reviews, more things to do, and more tourist information, refer to the Charlottesville online journey planner .

Traveling by car from Williamsburg to Charlottesville takes 2.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Charlottesville can reach 84°F, while at night they dip to 64°F. Finish your sightseeing early on the 23rd (Sun) to allow enough time to travel back home.

Things to do in Charlottesville

Wineries Shopping Historic Sites

Side Trip

King Family Vineyards
Highlights from your plan
King Family Vineyards ©
King Family Vineyards
Monticello ©
Monticello
Jefferson Vineyards ©
Jefferson Vineyards

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