8 days in Coastal Virginia - Eastern Shore Itinerary

8 days in Coastal Virginia - Eastern Shore Itinerary

Created using Inspirock Coastal Virginia - Eastern Shore journey maker

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Route & dates

8 days in Coastal Virginia - Eastern Shore Itinerary

Start: Chicago
Fly:  4​h 30​min
1
Virginia Beach
— 3 nights
Drive:  2​h 30​min
2
Chincoteague Island
— 2 nights
Drive:  3​h
3
Williamsburg
— 2 nights
+2
bus + taxi + Fly:  5​h 30​min
End: Chicago

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.
Visit Virginia Beach and Sandbridge Beach for some beach relaxation. You'll visit kid-friendly attractions like Cape Charles Beach and Parasailing & Paragliding. Go for a jaunt from Virginia Beach to Machipongo to see Barrier Islands Center about 1h 05 min away. There's still lots to do: take in the waterfront at Virginia Beach Boardwalk, see the interesting displays at Virginia Beach Surf & Rescue Museum, get your game on at Flipper McCoys, and enjoy the sand and surf at Chicks Beach.

For other places to visit, where to stay, reviews, and tourist information, you can read our Virginia Beach trip planner .

Chicago to Virginia Beach is an approximately 4.5-hour flight. You can also drive; or take a train. You'll lose 1 hour traveling from Chicago to Virginia Beach due to the time zone difference. In July, Virginia Beach is somewhat warmer than Chicago - with highs of 89°F and lows of 73°F. Wrap up your sightseeing on the 16th (Tue) to allow time to drive to Chincoteague Island.

Things to do in Virginia Beach

Outdoors Parks Beaches

Side Trips

Cape Charles Beach, Barrier Islands Center
Highlights from your plan
Virginia Beach ©
Virginia Beach
Sandbridge Beach ©
Sandbridge Beach

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 17th (Wed): look for all kinds of wild species at Chincoteague National Wildlife Refuge. Get ready for a full day of sightseeing on the next day: get a dose of the wild on a nature and wildlife tour, then get your game on at Surfside Golf, then stop by MamerSass, and finally view the masterpieces at Tryfan Gallery.

Find out how to plan Chincoteague Island trip without stress by asking Inspirock to help create an itinerary.

You can drive from Virginia Beach to Chincoteague Island in 2.5 hours. Other options are to take a bus; or take a bus. In July, daytime highs in Chincoteague Island are 86°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 18th (Thu) early enough to drive to Williamsburg.

Things to do in Chincoteague Island

Wildlife Parks Nature
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Surfside Golf ©
Surfside Golf

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): cool off at Busch Gardens Williamsburg. Get ready for a full day of sightseeing on the next day: steep yourself in history at Colonial Williamsburg, look for gifts at Yankee Candle Company, and then steep yourself in history at Jamestown Settlement.

To see more things to do, where to stay, ratings, and other tourist information, you can read our Williamsburg trip planner .

You can drive from Chincoteague Island to Williamsburg in 3 hours. Alternatively, you can take a bus. Expect a daytime high around 91°F in July, and nighttime lows around 73°F. Cap off your sightseeing on the 20th (Sat) early enough to travel back home.

Things to do in Williamsburg

Theme Parks Historic Sites Museums
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Jamestown Settlement ©
Jamestown Settlement
Yankee Candle Company ©
Yankee Candle Company