5 days in Eastern Shore Itinerary

5 days in Eastern Shore Itinerary

Created using Inspirock Eastern Shore journey planner

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Route & dates

5 days in Eastern Shore Itinerary

Start: Wilmington
Drive:  6​h
1
Crisfield
— 1 night
Drive:  1​h 45​min
2
St. Michaels
— 1 night
Drive:  1​h 45​min
3
Chesapeake City
— 2 nights
Drive + Fly:  4​h 45​min
End: Wilmington

1
night
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): see the interesting displays at Crisfield Heritage Foundation.

To see more things to do, traveler tips, where to stay, and other tourist information, you can read our Crisfield route maker tool .

Wilmington to Crisfield is an approximately 7-hour car ride. You can also do a combination of flight and car. In August, plan for daily highs up to 84°F, and evening lows to 68°F. Finish up your sightseeing early on the 27th (Tue) so you can go by car to St. Michaels.

Things to do in Crisfield

Museums Parks Nature

Side Trip

Delmarva Discovery Center
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Delmarva Discovery Center ©
Delmarva Discovery Center

1
night
St. Michaels

St. Michaels ©
On the 28th (Wed), enjoy the sea views from 1879 Hooper Strait Lighthouse, examine the collection at Chesapeake Bay Maritime Museum, and then explore the world behind art at Academy Art Museum.

To find reviews, photos, and tourist information, you can read our St. Michaels travel planner.

Getting from Crisfield to St. Michaels by car takes about 2 hours. In August, plan for daily highs up to 84°F, and evening lows to 67°F. Wrap up your sightseeing on the 28th (Wed) early enough to travel to Chesapeake City.

Things to do in St. Michaels

Museums Historic Sites

Side Trip

Academy Art Museum
Highlights from your plan
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse
Academy Art Museum ©
Academy Art Museum
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum

2
nights
Chesapeake City

Chesapeake City ©
Chesapeake City is a town in Cecil County, Maryland, USA. Kick off your visit on the 29th (Thu): take in the spiritual surroundings of Immanuel Episcopal Church, then get engrossed in the history at Dutch House Museum and Gardens, then steep yourself in history at Historic Odessa Foundation, and finally visit a coastal fixture at Concord Point Lighthouse. Get ready for a full day of sightseeing on the 30th (Fri): take an in-depth tour of Delaware Agricultural Museum and Village, then see the interesting displays at Johnson Victrola Museum, and then examine the collection at Susquehanna Museum at the Lock House.

For where to stay, other places to visit, more things to do, and more tourist information, read Chesapeake City road trip tool .

You can drive from St. Michaels to Chesapeake City in 1.5 hours. In August, daily temperatures in Chesapeake City can reach 84°F, while at night they dip to 66°F. Cap off your sightseeing on the 30th (Fri) early enough to travel back home.

Things to do in Chesapeake City

Historic Sites Museums

Side Trips

New Castle, Havre de Grace, Dover, Historic Odessa Foundation
Highlights from your plan
Historic Odessa Foundation ©
Historic Odessa Foundation
Johnson Victrola Museum ©
Johnson Victrola Museum

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