Solo Travelers Itineraries in Massachusetts

Flexible days, walkable routes, and stops that are just as good on your own — no plus-one required.

49 itineraries

Still Water, Quiet Mind: 4 Days Alone at Quabbin Reservoir

4 Days · Solo

Quabbin Reservoir area, Massachusetts

Still Water, Quiet Mind: 4 Days Alone at Quabbin Reservoir

7 stops

Brick, Steel & Spice: Two Days Solo in Worcester

2 Days · Solo

Worcester, Massachusetts, Massachusetts

Brick, Steel & Spice: Two Days Solo in Worcester

6 stops

Whimsy and Wonder: Two Days in Springfield's Quadrangle

2 Days · Solo

Springfield area, Massachusetts

Whimsy and Wonder: Two Days in Springfield's Quadrangle

4 stops

Stone, Ship, and Sea: Two Days Solo in Plymouth

2 Days · Solo

Plymouth, Massachusetts

Stone, Ship, and Sea: Two Days Solo in Plymouth

7 stops

Pages and Ponds: A Solo Wander Through Concord

2 Days · Solo

Concord, Massachusetts

Pages and Ponds: A Solo Wander Through Concord

5 stops

Salt Air & Gallows Hill: A Solo Wander Through Salem's Storied Streets

4 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Gallows Hill: A Solo Wander Through Salem's Storied Streets

6 stops

Salt Air & Solitude: 4 Days on Off-Season Nantucket

4 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Solitude: 4 Days on Off-Season Nantucket

10 stops

Dune Light & Quiet Tides: 4 Days Alone on the Outer Cape

4 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: 4 Days Alone on the Outer Cape

6 stops

Salt Air & Solitude: 4 Days Alone on Nantucket

4 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Solitude: 4 Days Alone on Nantucket

7 stops

Dune Light & Quiet Tides: A Solo Escape to Provincetown

4 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: A Solo Escape to Provincetown

8 stops

Cliffside Solitude: 4 Days Adrift on Martha's Vineyard

4 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliffside Solitude: 4 Days Adrift on Martha's Vineyard

6 stops

Still Water, Deep Woods: A Solo Retreat at Quabbin Reservoir

2 Days · Solo

Quabbin Reservoir area, Massachusetts

Still Water, Deep Woods: A Solo Retreat at Quabbin Reservoir

5 stops

Salt Air & Shadowed Streets: Two Days on Salem's Cobblestones

2 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Shadowed Streets: Two Days on Salem's Cobblestones

5 stops

Cliffs, Quiet, and Clay-Red Light: 2 Days Alone on Martha's Vineyard

2 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliffs, Quiet, and Clay-Red Light: 2 Days Alone on Martha's Vineyard

4 stops

Dune Light & Quiet Tides: Two Days Alone on the Outer Cape

2 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: Two Days Alone on the Outer Cape

5 stops

Roses, Fog, and Salt Air: A Solo Escape to Off-Season Nantucket

2 Days · Solo

Nantucket (off-season), Massachusetts

Roses, Fog, and Salt Air: A Solo Escape to Off-Season Nantucket

4 stops

Salt Air & Cobblestones: A Solo Weekend on Nantucket

2 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Cobblestones: A Solo Weekend on Nantucket

4 stops

Dune Light & Quiet Tides: A Solo Weekend in Provincetown

2 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: A Solo Weekend in Provincetown

5 stops

Clay, Light, and Salt Wind: Two Days Alone at Aquinnah

2 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Clay, Light, and Salt Wind: Two Days Alone at Aquinnah

4 stops

Salt Air & Old Secrets: Two Days Alone in Salem

2 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Old Secrets: Two Days Alone in Salem

3 stops

Brick, Blade, and Berbere: A Solo Wander Through Worcester

3 Days · Solo

Worcester, Massachusetts, Massachusetts

Brick, Blade, and Berbere: A Solo Wander Through Worcester

8 stops

Whimsy and Wonder: A Solo Springfield Weekend

3 Days · Solo

Springfield area, Massachusetts

Whimsy and Wonder: A Solo Springfield Weekend

3 stops

Brick, Blade, and Berbere: Three Days Alone in Worcester

3 Days · Solo

Worcester, Massachusetts, Massachusetts

Brick, Blade, and Berbere: Three Days Alone in Worcester

10 stops

Stone, Salt, and Slate: 3 Days Alone in Plymouth

3 Days · Solo

Plymouth, Massachusetts

Stone, Salt, and Slate: 3 Days Alone in Plymouth

8 stops

Pond Light & Parlor Doors: 3 Days Alone in Concord

3 Days · Solo

Concord, Massachusetts

Pond Light & Parlor Doors: 3 Days Alone in Concord

5 stops

Whimsy and Wonder: A Solo Journey Through Springfield's Quadrangle

3 Days · Solo

Springfield area, Massachusetts

Whimsy and Wonder: A Solo Journey Through Springfield's Quadrangle

6 stops

Stone, Sail & Slate: 3 Days Alone in Plymouth

3 Days · Solo

Plymouth, Massachusetts

Stone, Sail & Slate: 3 Days Alone in Plymouth

8 stops

Fallen Leaves & Transcendent Ground: 3 Days in Concord

3 Days · Solo

Concord, Massachusetts

Fallen Leaves & Transcendent Ground: 3 Days in Concord

8 stops

Fermented Leaves & Long Tables: Two Fall Days in Pioneer Valley

2 Days · Solo

Pioneer Valley, Massachusetts

Fermented Leaves & Long Tables: Two Fall Days in Pioneer Valley

4 stops

Still Water, Deep Woods: 3 Days Solo at Quabbin Reservoir

3 Days · Solo

Quabbin Reservoir area, Massachusetts

Still Water, Deep Woods: 3 Days Solo at Quabbin Reservoir

6 stops

Still Water, Quiet Company: 3 Days Alone at Quabbin

3 Days · Solo

Quabbin Reservoir area, Massachusetts

Still Water, Quiet Company: 3 Days Alone at Quabbin

6 stops

Salt Air & Empty Shores: 3 Days Alone on Off-Season Nantucket

3 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Empty Shores: 3 Days Alone on Off-Season Nantucket

6 stops

Dune Light & Quiet Company: 3 Days Solo on the Outer Cape

3 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Company: 3 Days Solo on the Outer Cape

5 stops

Cliff Light & Quiet Roads: A Solo Off-Season Escape to Martha's Vineyard

3 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliff Light & Quiet Roads: A Solo Off-Season Escape to Martha's Vineyard

5 stops

Salt Air & Shadowed Streets: Three Days Solo on the North Shore

3 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Shadowed Streets: Three Days Solo on the North Shore

6 stops

Sand, Silence & Salt Air: 3 Days Alone on the Outer Cape

3 Days · Solo

Cape Cod (off-season), Massachusetts

Sand, Silence & Salt Air: 3 Days Alone on the Outer Cape

6 stops

Cliffside Solitude: 3 Days Alone with Martha's Vineyard's Western Light

3 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliffside Solitude: 3 Days Alone with Martha's Vineyard's Western Light

4 stops

Salt Air & Solitude: 3 Days Alone on Nantucket

3 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Solitude: 3 Days Alone on Nantucket

4 stops

Salt Air & Old Secrets: Three Days Solo on Salem's Shore

3 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Old Secrets: Three Days Solo on Salem's Shore

4 stops

Brick, Steel, and Spice: Two Days in Worcester's Cultural Core

2 Days · Solo

Worcester, Massachusetts, Massachusetts

Brick, Steel, and Spice: Two Days in Worcester's Cultural Core

6 stops

Falling Leaves & Quiet Rooms: Two Days Alone in Concord

2 Days · Solo

Concord, Massachusetts

Falling Leaves & Quiet Rooms: Two Days Alone in Concord

5 stops

Stone, Sail & Salt Air: A Solo Pilgrimage to Plymouth

2 Days · Solo

Plymouth, Massachusetts

Stone, Sail & Salt Air: A Solo Pilgrimage to Plymouth

7 stops

Table & Trail: A Solo Culinary Amble Through Pioneer Valley

2 Days · Solo

Pioneer Valley, Massachusetts

Table & Trail: A Solo Culinary Amble Through Pioneer Valley

5 stops

Whimsy & Wonder: Two Days in the Springfield Quadrangle

2 Days · Solo

Springfield area, Massachusetts

Whimsy & Wonder: Two Days in the Springfield Quadrangle

4 stops

Falls, Farm Tables & Footlights: Two Days Savoring the Berkshires

2 Days · Solo

Berkshires (North/South), Massachusetts

Falls, Farm Tables & Footlights: Two Days Savoring the Berkshires

4 stops

Cobblestones & Copper Steeples: 3 Days Solo in Boston

3 Days · Solo

Boston Metro, Massachusetts

Cobblestones & Copper Steeples: 3 Days Solo in Boston

8 stops

Red Brick & Revolution: Two Days Walking Boston's Freedom Trail

2 Days · Solo

Boston Metro, Massachusetts

Red Brick & Revolution: Two Days Walking Boston's Freedom Trail

6 stops

Cobblestones & Candlelight: Two Days on Boston's Freedom Trail

2 Days · Solo

Boston Metro, Massachusetts

Cobblestones & Candlelight: Two Days on Boston's Freedom Trail

6 stops

Cobblestones & Candlelight: 3 Days Alone on the Freedom Trail

3 Days · Solo

Boston Metro, Massachusetts

Cobblestones & Candlelight: 3 Days Alone on the Freedom Trail

10 stops

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