Active Retirees Itineraries in Massachusetts

Comfortable pacing with real substance: scenic drives, guided moments, and time to actually linger.

17 itineraries

Dune Light & Gallery Quiet: 3 Days at the Cape's Outer Edge

3 Days · Active Retirees

Cape Cod (off-season), Massachusetts

Dune Light & Gallery Quiet: 3 Days at the Cape's Outer Edge

4 stops

Rose Lanes & Salt Air: 3 Days in Nantucket

3 Days · Active Retirees

Nantucket (off-season), Massachusetts

Rose Lanes & Salt Air: 3 Days in Nantucket

6 stops

Salt Air & Old Stories: Three Days on Salem's Cobblestones

3 Days · Active Retirees

North Shore (Salem area), Massachusetts

Salt Air & Old Stories: Three Days on Salem's Cobblestones

3 stops

Clay Cliffs & Quiet Light: A Slow Western Escape on Martha's Vineyard

3 Days · Active Retirees

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Light: A Slow Western Escape on Martha's Vineyard

4 stops

Still Waters: Three Days Beside the Quabbin

3 Days · Active Retirees

Quabbin Reservoir area, Massachusetts

Still Waters: Three Days Beside the Quabbin

5 stops

Slow Light and Long Tables: 3 Days in the Berkshires

3 Days · Active Retirees

Berkshires (North/South), Massachusetts

Slow Light and Long Tables: 3 Days in the Berkshires

3 stops

Slow Mornings & Long Tables: Two Days of Pioneer Valley Flavor

2 Days · Active Retirees

Pioneer Valley, Massachusetts

Slow Mornings & Long Tables: Two Days of Pioneer Valley Flavor

3 stops

Brick, Bronze & Blossoms: A Gentle Worcester Wander

3 Days · Active Retirees

Worcester, Massachusetts, Massachusetts

Brick, Bronze & Blossoms: A Gentle Worcester Wander

6 stops

Whimsy and Wonder: Three Unhurried Days in Springfield's Quadrangle

3 Days · Active Retirees

Springfield area, Massachusetts

Whimsy and Wonder: Three Unhurried Days in Springfield's Quadrangle

4 stops

Gables, Ghosts & Harbor Light: 3 Days on Salem's Historic Shore

3 Days · Active Retirees

North Shore (Salem area), Massachusetts

Gables, Ghosts & Harbor Light: 3 Days on Salem's Historic Shore

5 stops

Stone, Sail, and Salt Air: 3 Days in Historic Plymouth

3 Days · Active Retirees

Plymouth, Massachusetts

Stone, Sail, and Salt Air: 3 Days in Historic Plymouth

7 stops

Sea Roses & Whale Bone: Three Slow Days in Off-Season Nantucket

3 Days · Active Retirees

Nantucket (off-season), Massachusetts

Sea Roses & Whale Bone: Three Slow Days in Off-Season Nantucket

4 stops

Still Water, Long Light: 3 Days at Quabbin Reservoir

3 Days · Active Retirees

Quabbin Reservoir area, Massachusetts

Still Water, Long Light: 3 Days at Quabbin Reservoir

8 stops

Dunes, Light, and Quiet Rooms: 3 Days on the Outer Cape

3 Days · Active Retirees

Cape Cod (off-season), Massachusetts

Dunes, Light, and Quiet Rooms: 3 Days on the Outer Cape

5 stops

Clay, Light, and Quiet Tides: 3 Days on the Vineyard's Wild West End

3 Days · Active Retirees

Martha’s Vineyard (off-season), Massachusetts

Clay, Light, and Quiet Tides: 3 Days on the Vineyard's Wild West End

4 stops

Quiet Steps Through Concord: Literary Homes and a Glacial Pond

3 Days · Active Retirees

Concord, Massachusetts

Quiet Steps Through Concord: Literary Homes and a Glacial Pond

5 stops

Cobblestones & Quiet Mornings: 4 Days Along Boston's Freedom Trail

4 Days · Active Retirees

Boston Metro, Massachusetts

Cobblestones & Quiet Mornings: 4 Days Along Boston's Freedom Trail

9 stops

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