3 Days · Solo
Ocean City area, Maryland
Salt Air & Wild Horses: Three Days Solo in Ocean City
6 stops
2 Days · Active Retirees
Ocean City area, Maryland
Salt Air & Slow Mornings: Two Days Along Ocean City's Shore
3 stops
3 Days · Teen Families
Ocean City area, Maryland
Boardwalk Lights & Wild Ponies: A Family Weekend on Maryland's Coast
6 stops
3 Days · Active Retirees
Ocean City area, Maryland
Salt Air & Slow Mornings: 3 Days in Ocean City
5 stops
2 Days · Couples
Ocean City area, Maryland
Salt Air & Wild Horses: A Couples' Escape to Ocean City
4 stops
2 Days · Young Families
Ocean City area, Maryland
Salt Air & Small Steps: A Family Weekend in Ocean City
3 stops
3 Days · Couples
Ocean City area, Maryland
Salt Air & Wild Horses: 3 Days in Ocean City
6 stops
3 Days · Young Families
Ocean City area, Maryland
Salt Air & Small Steps: 3 Days in Ocean City for Little Explorers
5 stops
3 Days · Young Families
Ocean City area, Maryland
Salt Air & Small Steps: 3 Days in Ocean City with Little Ones
5 stops
3 Days · Couples
Ocean City area, Maryland
Salt Air & Wild Shores: 3 Days in Ocean City
6 stops
3 Days · Teen Families
Ocean City area, Maryland
Boardwalk Nights & Wild Shorelines: 3 Days in Ocean City
6 stops
2 Days · Teen Families
Ocean City area, Maryland
Boardwalk Nights & Wild Horse Mornings: 2 Days in Ocean City
4 stops
2 Days · Couples
Ocean City area, Maryland
Salt Air & Wild Shores: A Couples' Escape to Ocean City
4 stops
2 Days · Young Families
Ocean City area, Maryland
Sandcastles & Sea Ponies: Two Easy Days in Ocean City
3 stops
3 Days · Young Families
Annapolis area, Maryland
Sailboats, Sandcastles & State House Steps: 3 Days in Annapolis with Little Ones
6 stops
2 Days · Solo
Patapsco Valley (Ellicott City, Sykesville), Maryland
Millstone & Mist: A Solo Fall Wander Through the Patapsco Valley
6 stops
3 Days · Couples
Annapolis area, Maryland
Brick, Bay & Sailcloth: A Spring Escape to Annapolis
6 stops
2 Days · Solo
Annapolis area, Maryland
Brick, Bay, and Solitude: Two Days in Annapolis
5 stops
3 Days · Teen Families
Baltimore area, Maryland
Salt Air & Star-Spangled Days: 3 Days in Baltimore
9 stops
2 Days · Solo
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Quiet: Two Days Alone on Maryland's Eastern Shore
6 stops
3 Days · Couples
Baltimore area, Maryland
Harbor Light & Hallowed Ground: Three Fall Days in Baltimore
9 stops
3 Days · Couples
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Glow: 3 Days on Maryland's Eastern Shore
6 stops
3 Days · Active Retirees
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Wildflowers: Three Slow Days in the Patapsco Valley
6 stops
3 Days · Active Retirees
Ocean City area, Maryland
Salt Air & Wild Shores: 3 Days in Ocean City
4 stops
3 Days · Couples
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Light & River Song: Three Days in the Patapsco Valley
8 stops
3 Days · Active Retirees
Annapolis area, Maryland
Brick, Bay & Bloom: Three Unhurried Days in Annapolis
6 stops
3 Days · Active Retirees
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light and Harbor Bells: A Gentle Eastern Shore Amble
6 stops
3 Days · Young Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Sandy Toes: An Eastern Shore Family Escape
5 stops
3 Days · Young Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & River Giggles: 3 Days in Patapsco Valley with Little Ones
6 stops
3 Days · Solo
Baltimore area, Maryland
Harbor Light & Cobblestone Nights: 3 Days Solo in Baltimore
11 stops
Maryland's weekend getaways span coastal charm, historic towns, and scenic valleys—each with itineraries tailored to different travel styles and seasons. This collection features 16 curated itineraries across five key destinations: Annapolis area, Patapsco Valley, Baltimore area, Eastern Shore, and Ocean City area. Whether traveling solo, with family, or seeking a spring escape or fall retreat, visitors will find options ranging from two to three days that highlight local history, natural beauty, and waterfront experiences.
Frequently Asked Questions
What types of itineraries are available?⌄
The collection includes 16 itineraries designed for various travel styles: family-focused escapes, solo adventures, and seasonal getaways. Itineraries range from 2 to 3 days and span destinations including Annapolis, Patapsco Valley, Baltimore, Eastern Shore, and Ocean City.
Which destinations are covered in this guide?⌄
The guide features five main destinations: Annapolis area, Patapsco Valley (including Ellicott City and Sykesville), Baltimore area, Eastern Shore (including Chestertown, Easton, and St. Michaels), and Ocean City area.
Are there itineraries for families with children?⌄
Yes. Family-focused itineraries are available, including 'Sailboats, Sandcastles & State House Steps' in Annapolis, 'Mill Wheels & River Giggles' in Patapsco Valley, and 'Marsh Light & Sandy Toes' on the Eastern Shore.
What about solo travel options?⌄
Solo travelers have several options, including 'Millstone & Mist: A Solo Fall Wander Through the Patapsco Valley,' 'Marsh Light & Harbor Quiet: Two Days Alone on Maryland's Eastern Shore,' and 'Harbor Light & Cobblestone Nights: 3 Days Solo in Baltimore.'
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Or browse every Maryland destination.