5 days in Maryland Itinerary

5 days in Maryland Itinerary

Created using Inspirock Maryland travel route builder

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Route & dates

5 days in Maryland Itinerary

Start: Wilmington
+2
Fly + subway + train:  4​h 15​min
1
Baltimore
— 1 night
Drive:  1​h 45​min
2
St. Michaels
— 1 night
Drive:  1​h 45​min
3
Ocean City
— 1 night
Drive:  1​h 15​min
4
Crisfield
— 1 night
Drive:  6​h
End: Wilmington

1
night
Baltimore

Baltimore ©
A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
Kick off your visit on the 26th (Mon): brush up on your military savvy at U.S. Naval Academy. On your second day here, meet the residents at National Aquarium, then try your luck at Horseshoe Casino, and then take in the history at Fort McHenry National Monument.

To find traveler tips, other places to visit, photos, and tourist information, read our Baltimore travel route planner.

Wilmington to Baltimore is an approximately 4.5-hour combination of flight and train. You can also do a combination of flight, bus, subway, and train; or drive. In August, plan for daily highs up to 86°F, and evening lows to 71°F. Wrap up your sightseeing on the 27th (Tue) early enough to drive to St. Michaels.

Things to do in Baltimore

Parks Casinos Fun & Games

Side Trip

U.S. Naval Academy
Highlights from your plan
National Aquarium ©
National Aquarium
Horseshoe Casino ©
Horseshoe Casino

1
night
St. Michaels

St. Michaels ©
Start off your visit on the 28th (Wed): take in the exciting artwork at Ouvert Gallery, enjoy the sea views from 1879 Hooper Strait Lighthouse, see the interesting displays at Chesapeake Bay Maritime Museum, then indulge your thirst for a good beer at Eastern Shore Brewing, and finally sample the fine beverages at Lyon Distilling Company.

For where to stay, other places to visit, and tourist information, read St. Michaels attractions planning website .

Drive from Baltimore to St. Michaels in 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. August in St. Michaels sees daily highs of 84°F and lows of 67°F at night. Finish your sightseeing early on the 28th (Wed) so you can drive to Ocean City.

Things to do in St. Michaels

Museums Breweries & Distilleries Historic Sites
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Lyon Distilling Company ©
Lyon Distilling Company
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse

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.
On the 29th (Thu), tour the pleasant surroundings at Ocean City Beach, glide peacefully along the water with some of the best stand-up paddleboarding in the area, and then take a leisurely stroll along Ocean City Boardwalk.

To see where to stay, other places to visit, and more tourist information, read Ocean City trip builder website .

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can take a bus. In August, daytime highs in Ocean City are 82°F, while nighttime lows are 67°F. Cap off your sightseeing on the 29th (Thu) early enough to go by car to Crisfield.

Things to do in Ocean City

Outdoors Adventure Tours
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Stand-Up Paddleboarding

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. Your day-by-day itinerary now includes Smith Island. On the 30th (Fri), head off the coast to Smith Island, take in the waterfront activity at Somers Cove Marina, and then admire the majestic nature at Janes Island State Park.

To see more things to do, photos, where to stay, and other tourist information, read our Crisfield trip planner .

You can drive from Ocean City to Crisfield in 1.5 hours. In August, daytime highs in Crisfield are 84°F, while nighttime lows are 68°F. Wrap up your sightseeing on the 30th (Fri) early enough to travel back home.

Things to do in Crisfield

Parks Nature
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Somers Cove Marina ©
Somers Cove Marina

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