Solo Travelers Itineraries in Massachusetts

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

7 itineraries

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 & 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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