Active Retirees Itineraries in Massachusetts

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

38 itineraries

Whimsy and Wonder: A Gentle Two Days in the Springfield Quadrangle

2 Days · Active Retirees

Springfield area, Massachusetts

Whimsy and Wonder: A Gentle Two Days in the Springfield Quadrangle

3 stops

Brick, Bronze & Blossoms: A Gentle Two Days in Worcester

2 Days · Active Retirees

Worcester, Massachusetts, Massachusetts

Brick, Bronze & Blossoms: A Gentle Two Days in Worcester

4 stops

Falling Leaves & Quiet Pages: Two Days in Concord

2 Days · Active Retirees

Concord, Massachusetts

Falling Leaves & Quiet Pages: Two Days in Concord

4 stops

Stone, Sail & Slate: Two Autumn Days in Plymouth

2 Days · Active Retirees

Plymouth, Massachusetts

Stone, Sail & Slate: Two Autumn Days in Plymouth

5 stops

Brick, Bronze, and Autumn Light: Two Days in Worcester

2 Days · Active Retirees

Worcester, Massachusetts, Massachusetts

Brick, Bronze, and Autumn Light: Two Days in Worcester

5 stops

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

2 Days · Active Retirees

Springfield area, Massachusetts

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

3 stops

Stone, Sail & Slate: Three Autumn Days in Plymouth

3 Days · Active Retirees

Plymouth, Massachusetts

Stone, Sail & Slate: Three Autumn Days in Plymouth

8 stops

Cobblestones & Quiet Mornings: 3 Days Along Boston's Freedom Trail

3 Days · Active Retirees

Boston Metro, Massachusetts

Cobblestones & Quiet Mornings: 3 Days Along Boston's Freedom Trail

6 stops

Museum Light and Quiet Streets: Three Days in Springfield

3 Days · Active Retirees

Springfield area, Massachusetts

Museum Light and Quiet Streets: Three Days in Springfield

5 stops

Brick, Bronze, and Autumn Light: 3 Days in Worcester

3 Days · Active Retirees

Worcester, Massachusetts, Massachusetts

Brick, Bronze, and Autumn Light: 3 Days in Worcester

6 stops

Autumn Light on Author's Ridge: 3 Days in Concord

3 Days · Active Retirees

Concord, Massachusetts

Autumn Light on Author's Ridge: 3 Days in Concord

5 stops

Amber Light & Harvest Tables: 2 Days in Pioneer Valley

2 Days · Active Retirees

Pioneer Valley, Massachusetts

Amber Light & Harvest Tables: 2 Days in Pioneer Valley

3 stops

Still Water, Slow Days: Two Mornings at Quabbin Reservoir

2 Days · Active Retirees

Quabbin Reservoir area, Massachusetts

Still Water, Slow Days: Two Mornings at Quabbin Reservoir

4 stops

Dune Light and Gallery Quiet: Two Days on the Outer Cape

2 Days · Active Retirees

Cape Cod (off-season), Massachusetts

Dune Light and Gallery Quiet: Two Days on the Outer Cape

3 stops

Salt Air & Slow Roses: Two Days in Off-Season Nantucket

2 Days · Active Retirees

Nantucket (off-season), Massachusetts

Salt Air & Slow Roses: Two Days in Off-Season Nantucket

3 stops

Salt Air & Storied Streets: Two Days in Salem

2 Days · Active Retirees

North Shore (Salem area), Massachusetts

Salt Air & Storied Streets: Two Days in Salem

3 stops

Cliffside Light: Two Slow Days at Martha's Vineyard's Western Edge

2 Days · Active Retirees

Martha’s Vineyard (off-season), Massachusetts

Cliffside Light: Two Slow Days at Martha's Vineyard's Western Edge

4 stops

Dune Light & Gallery Quiet: Two Days on the Outer Cape

2 Days · Active Retirees

Cape Cod (off-season), Massachusetts

Dune Light & Gallery Quiet: Two Days on the Outer Cape

3 stops

Salted Gables: Two Slow Days in Historic Salem

2 Days · Active Retirees

North Shore (Salem area), Massachusetts

Salted Gables: Two Slow Days in Historic Salem

3 stops

Roses, Whales, and Slow Tides: Two Days in Nantucket

2 Days · Active Retirees

Nantucket (off-season), Massachusetts

Roses, Whales, and Slow Tides: Two Days in Nantucket

4 stops

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: 3 Days on Boston's Freedom Trail

3 Days · Active Retirees

Boston Metro, Massachusetts

Cobblestones & Quiet Mornings: 3 Days on Boston's Freedom Trail

6 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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