5 days in Eastern Shore Itinerary

5 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore visit planner

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Route & dates

5 days in Eastern Shore Itinerary

Start: Wilmington
Drive:  6​h
1
Crisfield
— Few hours
Drive:  1​h 15​min
2
Ocean City
— 1 night
Drive:  1​h 45​min
3
St. Michaels
— 3 nights
+3
bus + Fly + taxi + bus:  6​h 30​min
End: Wilmington

few
hours
Crisfield

Crisfield ©
Crisfield is a city in Somerset County, Maryland, United States, located on the Tangier Sound, an arm of the Chesapeake Bay. Start off your visit on the 26th (Mon): examine the collection at Crisfield Heritage Foundation.

For traveler tips, where to stay, maps, and more tourist information, read our Crisfield holiday builder site .

Wilmington to Crisfield is an approximately 7-hour car ride. You can also do a combination of flight and car. In August, daytime highs in Crisfield are 84°F, while nighttime lows are 68°F. Wrap up your sightseeing on the 26th (Mon) to allow time to drive to Ocean City.

Things to do in Crisfield

Museums
Highlights from your plan
Crisfield Heritage Foundation ©
Crisfield Heritage Foundation

1
night
Ocean City

Ocean City ©
One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
Kick off your visit on the 27th (Tue): examine the collection at Ocean City Life-Saving Station Museum, then don't miss a visit to Main Street Berlin, and then enjoy the sand and surf at Ocean City Beach.

To find other places to visit, maps, photos, and tourist information, you can read our Ocean City trip planner .

Getting from Crisfield to Ocean City by car takes about 1.5 hours. August in Ocean City sees daily highs of 82°F and lows of 67°F at night. Finish your sightseeing early on the 27th (Tue) so you can drive to St. Michaels.

Things to do in Ocean City

Historic Sites Beaches Outdoors

Side Trip

Main Street Berlin
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Life-Saving Station Museum ©

3
nights
St. Michaels

St. Michaels ©
Museum-lovers will appreciate Chesapeake Bay Maritime Museum and 1879 Hooper Strait Lighthouse. Your inner history buff will appreciate Calvert Marine Museum and Drum Point Lighthouse and Maryland State House. Venture out of the city with trips to Annapolis (Annapolis Historic District & U.S. Naval Academy).

For reviews, photos, maps, and other tourist information, read our St. Michaels trip itinerary builder app .

Getting from Ocean City to St. Michaels by car takes about 2 hours. Other options: take a bus. August in St. Michaels sees daily highs of 84°F and lows of 67°F at night. Cap off your sightseeing on the 30th (Fri) early enough to travel back home.

Things to do in St. Michaels

Museums Historic Sites Neighborhoods

Side Trips

Annapolis, Calvert Marine Museum and Drum Point Lighthouse
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
U.S. Naval Academy ©
U.S. Naval Academy
Maryland State House ©
Maryland State House

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