8 days in Maryland Itinerary

8 days in Maryland Itinerary

Created using Inspirock Maryland vacation builder

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Route & dates

8 days in Maryland Itinerary

Start: Milan
Fly:  14​h 45​min
1
Baltimore
— 3 nights
Drive:  1​h 30​min
2
Sharpsburg
— 1 night
Drive:  2​h 45​min
3
St. Michaels
— 1 night
Drive:  1​h 45​min
4
Ocean City
— 2 nights
bus + Fly:  17​h
End: Milan

3
nights
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.
Get some historical perspective at Fort McHenry National Monument and Historic Shrine and Fell's Point. The Walters Art Museum and Historic Ships in Baltimore will appeal to museum buffs. Change things up with a short trip to U.S. Naval Academy in Annapolis (about 40 minutes away). There's still lots to do: try to win big at Horseshoe Casino, sample the fine beverages at Sagamore Spirit Distillery, take in the architecture and atmosphere at Saint Alphonsus Church, and see the interesting displays at American Visionary Art Museum.

To see reviews, photos, maps, and more tourist information, read Baltimore trip planner .

Milan, Italy to Baltimore is an approximately 15-hour flight. You can also do a combination of flight and train; or do a combination of flight and train. Traveling from Milan to Baltimore, you'll gain 6 hours due to the time zone difference. Traveling from Milan in September, expect somewhat warmer with lows of 22°C in Baltimore. Finish your sightseeing early on the 26th (Thu) so you can drive to Sharpsburg.

Things to do in Baltimore

Parks Historic Sites Museums

Side Trip

U.S. Naval Academy
Highlights from your plan
U.S. Naval Academy ©
U.S. Naval Academy
The Walters Art Museum ©
The Walters Art Museum

1
night
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. On the 27th (Fri), steep yourself in history at Tolson's Chapel, then witness the site of a historic battle at Antietam National Battlefield, and then take in the pleasant sights at The Hagerstown Cultural Trail.

For traveler tips, where to stay, other places to visit, and more tourist information, go to the Sharpsburg trip app .

Getting from Baltimore to Sharpsburg by car takes about 1.5 hours. Traveling from Baltimore in September, you can expect nighttime temperatures to be little chillier in Sharpsburg, with lows of 15°C. Wrap up your sightseeing on the 27th (Fri) early enough to travel to St. Michaels.

Things to do in Sharpsburg

Historic Sites Parks Nature

Side Trip

The Hagerstown Cultural Trail
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Tolson's Chapel ©
Tolson's Chapel
The Hagerstown Cultural Trail ©
The Hagerstown Cultural Trail

1
night
St. Michaels

St. Michaels ©
Kick off your visit on the 28th (Sat): shop like a local with Ouvert Gallery, enjoy the sea views from 1879 Hooper Strait Lighthouse, see the interesting displays at Chesapeake Bay Maritime Museum, then sample the fine beverages at Lyon Distilling Company, and finally see the interesting displays at Tilghman Watermans Museum.

For more things to do, photos, reviews, and other tourist information, use the St. Michaels trip itinerary builder .

Drive from Sharpsburg to St. Michaels in 3 hours. Traveling from Sharpsburg in September, you can expect nighttime temperatures to be somewhat warmer in St. Michaels, with lows of 19°C. Cap off your sightseeing on the 28th (Sat) early enough to go by car to Ocean City.

Things to do in St. Michaels

Museums Historic Sites Breweries & Distilleries

Side Trip

Tilghman Watermans Museum
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse
Tilghman Watermans Museum ©
Tilghman Watermans Museum

2
nights
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 29th (Sun): contemplate the long history of Calvin B. Taylor House Museum, then examine the collection at Ocean City Life-Saving Station Museum, then kick back and relax at Ocean City Beach, and finally take in the waterfront at Ocean City Boardwalk.

For where to stay, more things to do, traveler tips, and tourist information, you can read our Ocean City road trip planning website .

You can drive from St. Michaels to Ocean City in 2 hours. Alternatively, you can take a bus. September in Ocean City sees daily highs of 30°C and lows of 20°C at night. Finish up your sightseeing early on the 30th (Mon) so you can travel back home.

Things to do in Ocean City

Outdoors Beaches Parks

Side Trip

Calvin B. Taylor House Museum
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Calvin B. Taylor House Museum ©
Calvin B. Taylor House Museum
Ocean City Life-Saving Station Museum ©

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