
3 Days · Active Retirees
Cape Cod (off-season), Massachusetts
Dune Light & Gallery Quiet: 3 Days at the Cape's Outer Edge
4 stops

3 Days · Active Retirees
Nantucket (off-season), Massachusetts
Rose Lanes & Salt Air: 3 Days in Nantucket
6 stops

3 Days · Active Retirees
North Shore (Salem area), Massachusetts
Salt Air & Old Stories: Three Days on Salem's Cobblestones
3 stops

3 Days · Active Retirees
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Light: A Slow Western Escape on Martha's Vineyard
4 stops

3 Days · Young Families
Martha’s Vineyard (off-season), Massachusetts
Cliffside Quiet: 3 Days of Wildflowers and Sea Wind on Martha's Vineyard
4 stops

3 Days · Young Families
North Shore (Salem area), Massachusetts
Gables, Gulls, and Gentle Museum Hours: 3 Days in Salem with Little Ones
3 stops

3 Days · Young Families
Cape Cod (off-season), Massachusetts
Dunes, Tide Pools & Quiet Galleries: 3 Days in Off-Season Cape Cod
4 stops

3 Days · Young Families
Nantucket (off-season), Massachusetts
Rose Lanes & Quiet Tides: 3 Days in Off-Season Nantucket
6 stops

3 Days · Couples
North Shore (Salem area), Massachusetts
Salted Air & Old Doorways: 3 Days on the North Shore
5 stops

3 Days · Couples
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Light: 3 Days in Off-Season Martha's Vineyard
4 stops

3 Days · Couples
Cape Cod (off-season), Massachusetts
Dune Light & Quiet Tides: 3 Days in Off-Season Provincetown
5 stops

3 Days · Couples
Nantucket (off-season), Massachusetts
Salt Air & Slow Light: 3 Days in Off-Season Nantucket
6 stops

3 Days · Couples
North Shore (Salem area), Massachusetts
Salt Air & Seven Gables: A North Shore Romance
5 stops

3 Days · Young Families
Cape Cod (off-season), Massachusetts
Sandy Toes & Slow Mornings: 3 Days in Off-Season Cape Cod
5 stops

3 Days · Couples
Cape Cod (off-season), Massachusetts
Dune Light & Quiet Tides: 3 Days in Provincetown
6 stops

3 Days · Couples
Nantucket (off-season), Massachusetts
Salt Air & Slow Light: 3 Days in Nantucket for Two
5 stops

3 Days · Young Families
Martha’s Vineyard (off-season), Massachusetts
Cliffside Hours: A Gentle Family Escape to Aquinnah
4 stops

3 Days · Young Families
Nantucket (off-season), Massachusetts
Sand Between Their Toes: 3 Days in Nantucket for Little Explorers
5 stops

3 Days · Couples
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Light: 3 Days in Martha's Vineyard
4 stops

3 Days · Young Families
North Shore (Salem area), Massachusetts
Gables, Gulls & Gentle History: 3 Days in Salem with Little Ones
3 stops

3 Days · Active Retirees
Quabbin Reservoir area, Massachusetts
Still Waters: Three Days Beside the Quabbin
5 stops

3 Days · Couples
Quabbin Reservoir area, Massachusetts
Still Water, Slow Light: 3 Days at Quabbin Reservoir
7 stops

3 Days · Young Families
Quabbin Reservoir area, Massachusetts
Still Water Days: A Family Weekend at Quabbin Reservoir
4 stops

3 Days · Active Retirees
Berkshires (North/South), Massachusetts
Slow Light and Long Tables: 3 Days in the Berkshires
3 stops

3 Days · Young Families
Worcester, Massachusetts, Massachusetts
Brick, Park & Piri-Piri: 3 Slow Days in Worcester with Little Ones
4 stops

3 Days · Active Retirees
Worcester, Massachusetts, Massachusetts
Brick, Bronze & Blossoms: A Gentle Worcester Wander
6 stops

3 Days · Couples
Worcester, Massachusetts, Massachusetts
Brick, Steel & Spice: A Slow Worcester Weekend
9 stops

3 Days · Couples
Springfield area, Massachusetts
Whimsy and Wonder: A Quadrangle Escape in Springfield
3 stops

3 Days · Couples
Plymouth, Massachusetts
Salt Air & Slate Stones: A Plymouth Weekend for Two
10 stops

3 Days · Active Retirees
Springfield area, Massachusetts
Whimsy and Wonder: Three Unhurried Days in Springfield's Quadrangle
4 stops

3 Days · Active Retirees
North Shore (Salem area), Massachusetts
Gables, Ghosts & Harbor Light: 3 Days on Salem's Historic Shore
5 stops

3 Days · Young Families
Plymouth, Massachusetts
Rock, Rope & Grindstone: 3 Slow Days in Plymouth with Little Ones
6 stops

3 Days · Active Retirees
Plymouth, Massachusetts
Stone, Sail, and Salt Air: 3 Days in Historic Plymouth
7 stops

3 Days · Active Retirees
Nantucket (off-season), Massachusetts
Sea Roses & Whale Bone: Three Slow Days in Off-Season Nantucket
4 stops

3 Days · Active Retirees
Quabbin Reservoir area, Massachusetts
Still Water, Long Light: 3 Days at Quabbin Reservoir
8 stops

3 Days · Young Families
Springfield area, Massachusetts
Whimsy on Chestnut Street: A Family Weekend in Springfield's Quadrangle
4 stops

3 Days · Couples
Concord, Massachusetts
Wildflowers & Wood Smoke: 3 Days of Romance in Concord
6 stops

3 Days · Active Retirees
Cape Cod (off-season), Massachusetts
Dunes, Light, and Quiet Rooms: 3 Days on the Outer Cape
5 stops

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

3 Days · Young Families
Concord, Massachusetts
Little Women & Big Woods: A Family Wander Through Concord
4 stops

3 Days · Couples
Quabbin Reservoir area, Massachusetts
Still Water, Slow Days: A Quabbin Reservoir Escape for Two
6 stops

3 Days · Active Retirees
Concord, Massachusetts
Quiet Steps Through Concord: Literary Homes and a Glacial Pond
5 stops

3 Days · Teen Families
Boston Metro, Massachusetts
Cobblestones, Tea Parties & Midnight Rides: 3 Days on Boston's Freedom Trail
8 stops

3 Days · Couples
Boston Metro, Massachusetts
Cobblestones & Candlelight: A Boston Autumn for Two
9 stops

3 Days · Solo
Boston Metro, Massachusetts
Cobblestones & Candlelight: 3 Days Alone on the Freedom Trail
10 stops
More Collections
Or see 3-Day Itineraries nationwide or browse every Massachusetts destination.