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
2 Days · Solo
Annapolis area, Maryland
Brick, Bay, and Quiet Water: 2 Days in Annapolis
5 stops
2 Days · Active Retirees
Baltimore area, Maryland
Harbor Light & Harbor History: Two Easy Days in Baltimore
5 stops
2 Days · Active Retirees
Baltimore area, Maryland
Harbor Light & Harbor Lore: Two Easy Days in Baltimore
6 stops
2 Days · Active Retirees
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Harbor Light & Marsh Song: Two Slow Days on Maryland's Eastern Shore
4 stops
2 Days · Active Retirees
Annapolis area, Maryland
Brick, Bay, and Quiet Water: Two Easy Days in Annapolis
5 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
2 Days · Active Retirees
Ocean City area, Maryland
Salt Air & Sand Dollars: A Gentle Two Days in Ocean City
4 stops
3 Days · Teen Families
Annapolis area, Maryland
Brick, Bay & Breeze: 3 Days in Annapolis for Teen Families
8 stops
2 Days · Active Retirees
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Waterlight and Wide Skies: Two Days on Maryland's Eastern Shore
4 stops
3 Days · Teen Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
River Mist & Mill Stones: 3 Days in the Patapsco Valley
9 stops
3 Days · Teen Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Working Waterfronts: 3 Days on Maryland's Eastern Shore
6 stops
2 Days · Active Retirees
Patapsco Valley (Ellicott City, Sykesville), Maryland
Millstones & Main Street: Two Autumn Days in the Patapsco Valley
6 stops
2 Days · Active Retirees
Annapolis area, Maryland
Brick, Bay, and Quiet Water: Two Days in Annapolis
4 stops
3 Days · Solo
Annapolis area, Maryland
Brick, Bay, and Solitude: 3 Days in Annapolis
9 stops
3 Days · Teen Families
Baltimore area, Maryland
Harbor Light & Old Bay Nights: 3 Days in Baltimore
9 stops
3 Days · Solo
Annapolis area, Maryland
Brick, Bay, and Bell Towers: A Solo Autumn in Annapolis
6 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
Baltimore area, Maryland
Harbor Light, Fort Walls & Forest Falls: 3 Days Solo in Baltimore
10 stops
3 Days · Teen Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Wheels & Waterfalls: Three Fall Days in the Patapsco Valley
10 stops
3 Days · Teen Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Towns: 3 Days on Maryland's Eastern Shore
6 stops
3 Days · Teen Families
Annapolis area, Maryland
Brick, Bay & Breeze: A Teen Family Weekend in Annapolis
6 stops
2 Days · Couples
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Light & River Song: Two Days in the Patapsco Valley
6 stops
2 Days · Young Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Cobblestones and Cascades: A Family Weekend in the Patapsco Valley
3 stops
2 Days · Young Families
Patapsco Valley (Ellicott City, Sykesville), Maryland
Cobblestones & Cascades: A Family Weekend in the Patapsco Valley
4 stops
2 Days · Couples
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Waterlight & Wild Marsh: A Two-Day Eastern Shore Escape
5 stops
2 Days · Young Families
Annapolis area, Maryland
Sailboats, Storybook Streets & Salt Air: 2 Days in Annapolis with Little Ones
4 stops
2 Days · Young Families
Baltimore area, Maryland
Splash Pools & Star-Spangled Skies: A Family Weekend in Baltimore
4 stops
3 Days · Active Retirees
Baltimore area, Maryland
Harbor Light & Hallowed Ground: Three Autumn Days in Baltimore
10 stops
2 Days · Couples
Patapsco Valley (Ellicott City, Sykesville), Maryland
Mill Light & River Song: A Fall Escape to the Patapsco Valley
4 stops
2 Days · Couples
Baltimore area, Maryland
Harbor Light & Fort Walls: A Baltimore Weekend for Two
7 stops
3 Days · Active Retirees
Patapsco Valley (Ellicott City, Sykesville), Maryland
Millstones & Foliage: Three Autumn Days in the Patapsco Valley
8 stops
2 Days · Young Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Wooden Boats & Wide-Open Marshes: A Family Weekend on Maryland's Eastern Shore
3 stops
2 Days · Couples
Annapolis area, Maryland
Brick, Bay, and Sailboat Light: Two Days in Annapolis
5 stops
2 Days · Young Families
Annapolis area, Maryland
Sailboats, Statehouses & Sandy Toes: A Family Weekend in Annapolis
4 stops
3 Days · Active Retirees
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Water Light & Wooden Boats: Three Days on the Eastern Shore
6 stops
2 Days · Young Families
Baltimore area, Maryland
Splash, Sail, and Stroll: A Gentle Baltimore Harbor Weekend for Little Ones
3 stops
2 Days · Couples
Baltimore area, Maryland
Harbor Light & Cobblestone Nights: Two Days in Baltimore
7 stops
2 Days · Couples
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Marsh Light & Harbor Nights: A Two-Day Eastern Shore Escape
6 stops
2 Days · Young Families
Eastern Shore (Chestertown, Easton, St. Michaels), Maryland
Wooden Boats & Marsh Light: A Family Weekend on Maryland's Eastern Shore
4 stops
3 Days · Active Retirees
Baltimore area, Maryland
Harbor Light & Hallowed Ground: 3 Days in Baltimore
8 stops
2 Days · Couples
Annapolis area, Maryland
Brick, Sail & Marsh Light: Two Days in Annapolis
5 stops
3 Days · Active Retirees
Annapolis area, Maryland
Brick, Bay, and Marsh Light: Three Unhurried Days in Annapolis
6 stops
Showing 60 of 98 — explore all of Maryland.
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?
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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?
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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?
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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.