3-Day Itineraries in Maryland

Long-weekend trips with every day mapped out — verified attractions, realistic pacing.

48 itineraries

Salt Air & Wild Shores: 3 Days Solo in Ocean City

3 Days · Solo

Ocean City area, Maryland

Salt Air & Wild Shores: 3 Days Solo in Ocean City

5 stops

Marsh Light & Harbor Quiet: 3 Days Solo on Maryland's Eastern Shore

3 Days · Solo

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Harbor Quiet: 3 Days Solo on Maryland's Eastern Shore

6 stops

River Light & Mill Stone: 3 Days in the Patapsco Valley

3 Days · Solo

Patapsco Valley (Ellicott City, Sykesville), Maryland

River Light & Mill Stone: 3 Days in the Patapsco Valley

9 stops

Brick, Bay & Breeze: 3 Days in Annapolis for Teen Families

3 Days · Teen Families

Annapolis area, Maryland

Brick, Bay & Breeze: 3 Days in Annapolis for Teen Families

8 stops

River Mist & Mill Stones: 3 Days in the Patapsco Valley

3 Days · Teen Families

Patapsco Valley (Ellicott City, Sykesville), Maryland

River Mist & Mill Stones: 3 Days in the Patapsco Valley

9 stops

Marsh Light & Working Waterfronts: 3 Days on Maryland's Eastern Shore

3 Days · Teen Families

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Working Waterfronts: 3 Days on Maryland's Eastern Shore

6 stops

Brick, Bay, and Solitude: 3 Days in Annapolis

3 Days · Solo

Annapolis area, Maryland

Brick, Bay, and Solitude: 3 Days in Annapolis

9 stops

Harbor Light & Old Bay Nights: 3 Days in Baltimore

3 Days · Teen Families

Baltimore area, Maryland

Harbor Light & Old Bay Nights: 3 Days in Baltimore

9 stops

Brick, Bay, and Bell Towers: A Solo Autumn in Annapolis

3 Days · Solo

Annapolis area, Maryland

Brick, Bay, and Bell Towers: A Solo Autumn in Annapolis

6 stops

Marsh Light & Harbor Quiet: 3 Days Solo on Maryland's Eastern Shore

3 Days · Solo

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Harbor Quiet: 3 Days Solo on Maryland's Eastern Shore

6 stops

Harbor Light, Fort Walls & Forest Falls: 3 Days Solo in Baltimore

3 Days · Solo

Baltimore area, Maryland

Harbor Light, Fort Walls & Forest Falls: 3 Days Solo in Baltimore

10 stops

Mill Wheels & Waterfalls: Three Fall Days in the Patapsco Valley

3 Days · Teen Families

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Wheels & Waterfalls: Three Fall Days in the Patapsco Valley

10 stops

Marsh Light & Harbor Towns: 3 Days on Maryland's Eastern Shore

3 Days · Teen Families

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Harbor Towns: 3 Days on Maryland's Eastern Shore

6 stops

Brick, Bay & Breeze: A Teen Family Weekend in Annapolis

3 Days · Teen Families

Annapolis area, Maryland

Brick, Bay & Breeze: A Teen Family Weekend in Annapolis

6 stops

Harbor Light & Hallowed Ground: Three Autumn Days in Baltimore

3 Days · Active Retirees

Baltimore area, Maryland

Harbor Light & Hallowed Ground: Three Autumn Days in Baltimore

10 stops

Millstones & Foliage: Three Autumn Days in the Patapsco Valley

3 Days · Active Retirees

Patapsco Valley (Ellicott City, Sykesville), Maryland

Millstones & Foliage: Three Autumn Days in the Patapsco Valley

8 stops

Water Light & Wooden Boats: Three Days on the Eastern Shore

3 Days · Active Retirees

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Water Light & Wooden Boats: Three Days on the Eastern Shore

6 stops

Harbor Light & Hallowed Ground: 3 Days in Baltimore

3 Days · Active Retirees

Baltimore area, Maryland

Harbor Light & Hallowed Ground: 3 Days in Baltimore

8 stops

Brick, Bay, and Marsh Light: Three Unhurried Days in Annapolis

3 Days · Active Retirees

Annapolis area, Maryland

Brick, Bay, and Marsh Light: Three Unhurried Days in Annapolis

6 stops

Harbor Light & Fort Walls: 3 Days in Baltimore with Little Ones

3 Days · Young Families

Baltimore area, Maryland

Harbor Light & Fort Walls: 3 Days in Baltimore with Little Ones

7 stops

Mill Wheels & Maple Leaves: A Family Weekend in the Patapsco Valley

3 Days · Young Families

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Wheels & Maple Leaves: A Family Weekend in the Patapsco Valley

6 stops

Sailboats, Cobblestones & Quiet Waters: 3 Days in Annapolis with Little Ones

3 Days · Young Families

Annapolis area, Maryland

Sailboats, Cobblestones & Quiet Waters: 3 Days in Annapolis with Little Ones

4 stops

Marsh Light and Harbor Glow: 3 Days on Maryland's Eastern Shore

3 Days · Couples

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light and Harbor Glow: 3 Days on Maryland's Eastern Shore

6 stops

Harbor Light & Hilltop Views: A Baltimore Escape for Two

3 Days · Couples

Baltimore area, Maryland

Harbor Light & Hilltop Views: A Baltimore Escape for Two

9 stops

Splash Pads & Salt Air: 3 Gentle Days in Baltimore with Little Ones

3 Days · Young Families

Baltimore area, Maryland

Splash Pads & Salt Air: 3 Gentle Days in Baltimore with Little Ones

7 stops

Marsh Light & Harbor Days: 3 Days on Maryland's Eastern Shore with Little Ones

3 Days · Young Families

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Harbor Days: 3 Days on Maryland's Eastern Shore with Little Ones

6 stops

Brick, Sail & Marsh Light: A Chesapeake Weekend for Two

3 Days · Couples

Annapolis area, Maryland

Brick, Sail & Marsh Light: A Chesapeake Weekend for Two

6 stops

Salt Air & Wild Horses: Three Days Solo in Ocean City

3 Days · Solo

Ocean City area, Maryland

Salt Air & Wild Horses: Three Days Solo in Ocean City

6 stops

Boardwalk Lights & Wild Ponies: A Family Weekend on Maryland's Coast

3 Days · Teen Families

Ocean City area, Maryland

Boardwalk Lights & Wild Ponies: A Family Weekend on Maryland's Coast

6 stops

Salt Air & Slow Mornings: 3 Days in Ocean City

3 Days · Active Retirees

Ocean City area, Maryland

Salt Air & Slow Mornings: 3 Days in Ocean City

5 stops

Salt Air & Wild Horses: 3 Days in Ocean City

3 Days · Couples

Ocean City area, Maryland

Salt Air & Wild Horses: 3 Days in Ocean City

6 stops

Salt Air & Small Steps: 3 Days in Ocean City for Little Explorers

3 Days · Young Families

Ocean City area, Maryland

Salt Air & Small Steps: 3 Days in Ocean City for Little Explorers

5 stops

Salt Air & Small Steps: 3 Days in Ocean City with Little Ones

3 Days · Young Families

Ocean City area, Maryland

Salt Air & Small Steps: 3 Days in Ocean City with Little Ones

5 stops

Salt Air & Wild Shores: 3 Days in Ocean City

3 Days · Couples

Ocean City area, Maryland

Salt Air & Wild Shores: 3 Days in Ocean City

6 stops

Boardwalk Nights & Wild Shorelines: 3 Days in Ocean City

3 Days · Teen Families

Ocean City area, Maryland

Boardwalk Nights & Wild Shorelines: 3 Days in Ocean City

6 stops

Sailboats, Sandcastles & State House Steps: 3 Days in Annapolis with Little Ones

3 Days · Young Families

Annapolis area, Maryland

Sailboats, Sandcastles & State House Steps: 3 Days in Annapolis with Little Ones

6 stops

Brick, Bay & Sailcloth: A Spring Escape to Annapolis

3 Days · Couples

Annapolis area, Maryland

Brick, Bay & Sailcloth: A Spring Escape to Annapolis

6 stops

Salt Air & Star-Spangled Days: 3 Days in Baltimore

3 Days · Teen Families

Baltimore area, Maryland

Salt Air & Star-Spangled Days: 3 Days in Baltimore

9 stops

Harbor Light & Hallowed Ground: Three Fall Days in Baltimore

3 Days · Couples

Baltimore area, Maryland

Harbor Light & Hallowed Ground: Three Fall Days in Baltimore

9 stops

Marsh Light & Harbor Glow: 3 Days on Maryland's Eastern Shore

3 Days · Couples

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Harbor Glow: 3 Days on Maryland's Eastern Shore

6 stops

Mill Wheels & Wildflowers: Three Slow Days in the Patapsco Valley

3 Days · Active Retirees

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Wheels & Wildflowers: Three Slow Days in the Patapsco Valley

6 stops

Salt Air & Wild Shores: 3 Days in Ocean City

3 Days · Active Retirees

Ocean City area, Maryland

Salt Air & Wild Shores: 3 Days in Ocean City

4 stops

Mill Light & River Song: Three Days in the Patapsco Valley

3 Days · Couples

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Light & River Song: Three Days in the Patapsco Valley

8 stops

Brick, Bay & Bloom: Three Unhurried Days in Annapolis

3 Days · Active Retirees

Annapolis area, Maryland

Brick, Bay & Bloom: Three Unhurried Days in Annapolis

6 stops

Marsh Light and Harbor Bells: A Gentle Eastern Shore Amble

3 Days · Active Retirees

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light and Harbor Bells: A Gentle Eastern Shore Amble

6 stops

Marsh Light & Sandy Toes: An Eastern Shore Family Escape

3 Days · Young Families

Eastern Shore (Chestertown, Easton, St. Michaels), Maryland

Marsh Light & Sandy Toes: An Eastern Shore Family Escape

5 stops

Mill Wheels & River Giggles: 3 Days in Patapsco Valley with Little Ones

3 Days · Young Families

Patapsco Valley (Ellicott City, Sykesville), Maryland

Mill Wheels & River Giggles: 3 Days in Patapsco Valley with Little Ones

6 stops

Harbor Light & Cobblestone Nights: 3 Days Solo in Baltimore

3 Days · Solo

Baltimore area, Maryland

Harbor Light & Cobblestone Nights: 3 Days Solo in Baltimore

11 stops

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