Where to Go in Maryland
Character City
Eastern Shore (Chestertown, Easton, St. Michaels)
The Eastern Shore of Maryland is a timeless refuge where colonial charm meets working waterfront culture, dotted with picturesque villages like Chestertown, Easton, and St. Michaels that seem suspende
20 itineraries
Character City
Patapsco Valley (Ellicott City, Sykesville)
Nestled along the Patapsco River just outside Baltimore, the Patapsco Valley offers a captivating blend of colonial charm and natural refuge. Ellicott City's historic Main Street invites leisurely str
18 itineraries
Metro
Baltimore area
Baltimore is a city where American history comes alive along the waterfront, from the star-spangled banner's birth at Fort McHenry to the bustling charm of Inner Harbor. Nestled between rolling countr
24 itineraries
Character City
Annapolis area
Annapolis is where American history breathes along the Chesapeake Bay—a graceful colonial city that once served as the nation's capital and still radiates that dignified, purposeful charm. The waterfr
20 itineraries
Beach Coastal
Ocean City area
Ocean City is a classic American seaside escape where miles of sandy beaches meet a legendary boardwalk buzzing with nostalgic charm and modern energy. This Atlantic resort transforms from a sleepy co
30 itineraries
Maryland Itineraries
4 Days · Couples
Baltimore area, Maryland
Harbor Light & Rolling Water: Four Days in Baltimore
11 stops
4 Days · Couples
Baltimore area, Maryland
Harbor Light & Tidewater Grace: 4 Days in Baltimore
11 stops
2 Days · Teen Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Maritime Mornings: Two Days on Maryland's Eastern Shore
4 stops
2 Days · Teen Families
Annapolis area, Maryland
Brick, Bay & Bancroft Hall: Two Days in Annapolis
5 stops
2 Days · Teen Families
Baltimore area, Maryland
Harbor Light & Fort Walls: 2 Days in Baltimore with Teens
6 stops
2 Days · Solo
Baltimore area, Maryland
Harbor Light & Fort Walls: Two Days Solo in Baltimore
9 stops
2 Days · Teen Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Waterfronts & Wild Marshes: A Teen Family Escape on Maryland's Eastern Shore
4 stops
2 Days · Teen Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Waterfalls: Two Days Along the Patapsco
6 stops
2 Days · Teen Families
Baltimore area, Maryland
Harbor Lights & Fort Walls: 2 Days in Baltimore with Teens
7 stops
2 Days · Teen Families
Annapolis area, Maryland
Brick, Bay, and Byways: Two Fall Days in Annapolis
4 stops
2 Days · Solo
Baltimore area, Maryland
Harbor Light, Salt Air: 2 Days Solo in Baltimore
9 stops
2 Days · Solo
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Towns: A Solo Wander Through Maryland's Eastern Shore
5 stops