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
16 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
17 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
16 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
16 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
25 itineraries
Maryland Itineraries
4 Days · Young Families
Ocean City area, Maryland
Wild Ponies & Boardwalk Lights: 4 Days in Ocean City with Little Ones
6 stops
4 Days · Young Families
Ocean City area, Maryland
Sandy Toes & Salt Air: 4 Days in Ocean City with the Little Ones
6 stops
4 Days · Couples
Ocean City area, Maryland
Salt Air & Wild Horses: 4 Days on Maryland's Shoreline
9 stops
2 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Shores: A Solo Escape to Ocean City
4 stops
2 Days · Solo
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Wildflowers: A Solo Wander Through Patapsco Valley
5 stops
2 Days · Teen Families
Ocean City area, Maryland
Boardwalk Lights & Wild Shores: 2 Days in Ocean City
4 stops
2 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Horses: A Solo Weekend in Ocean City
4 stops
2 Days · Teen Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Town Light & River Trails: 2 Days in Patapsco Valley
5 stops
2 Days · Active Retirees
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Wildflowers: Two Easy Days in the Patapsco Valley
3 stops
3 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Shores: 3 Days Solo in Ocean City
5 stops
3 Days · Solo
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Quiet: 3 Days Solo on Maryland's Eastern Shore
6 stops
3 Days · Solo
Patapsco Valley (Ellicott City, Sykesville), Maryland
River Light & Mill Stone: 3 Days in the Patapsco Valley
9 stops