Spring Itineraries in Massachusetts

4 Days · Young Families

Cape Cod (off-season), Massachusetts

Dunes, Driftwood & Downtime: 4 Days in Off-Season Provincetown

5 stops

4 Days · Young Families

Nantucket (off-season), Massachusetts

Rose Lanes & Quiet Tides: 4 Days in Off-Season Nantucket

6 stops

4 Days · Young Families

Martha’s Vineyard (off-season), Massachusetts

Cliffside Quiet: A Family Slow-Down on Martha's Vineyard

5 stops

4 Days · Couples

Nantucket (off-season), Massachusetts

Salt Air & Winter Light: 4 Days of Off-Season Nantucket for Two

6 stops

4 Days · Couples

North Shore (Salem area), Massachusetts

Salt Air & Storied Streets: Four Days on Salem's North Shore

4 stops

4 Days · Couples

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: 4 Days in Off-Season Provincetown

7 stops

4 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

Cliff Light & Quiet Tides: 4 Days on Martha's Vineyard

6 stops

2 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Tides: Two Days Off-Season in Aquinnah

4 stops

2 Days · Solo

North Shore (Salem area), Massachusetts

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

5 stops

2 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

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

4 stops

2 Days · Solo

Cape Cod (off-season), Massachusetts

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

5 stops

2 Days · Teen Families

North Shore (Salem area), Massachusetts

Salt Air & Séance Bells: 2 Days in Salem

3 stops

2 Days · Solo

Nantucket (off-season), Massachusetts

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

4 stops

2 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dunes, Gray Light & Wild Shore: 2 Days in Off-Season Provincetown

4 stops

2 Days · Teen Families

Nantucket (off-season), Massachusetts

Roses, Wind, and Whale Bones: 2 Days in Off-Season Nantucket

4 stops

3 Days · Teen Families

Worcester, Massachusetts, Massachusetts

Brick, Blade & Berbere: Three Days in Worcester

9 stops

3 Days · Solo

Worcester, Massachusetts, Massachusetts

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

8 stops

3 Days · Teen Families

Springfield area, Massachusetts

Whimsy & Wonder: A Springfield Family Weekend in the Quadrangle

6 stops

2 Days · Active Retirees

Springfield area, Massachusetts

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

3 stops

3 Days · Solo

Springfield area, Massachusetts

Whimsy and Wonder: A Solo Springfield Weekend

3 stops

2 Days · Active Retirees

Worcester, Massachusetts, Massachusetts

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

4 stops

3 Days · Teen Families

Plymouth, Massachusetts

Rock, Rope & Rising Tide: 3 Days in Plymouth

10 stops

3 Days · Solo

Plymouth, Massachusetts

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

8 stops

3 Days · Solo

Concord, Massachusetts

Pond Light & Parlor Doors: 3 Days Alone in Concord

5 stops

3 Days · Teen Families

Concord, Massachusetts

Little Women, Big Ideas: A Concord Family Weekend

8 stops

2 Days · Young Families

Springfield area, Massachusetts

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

4 stops

2 Days · Couples

Plymouth, Massachusetts

Rock, Sail & Harbor Light: Two Days in Plymouth

6 stops

2 Days · Couples

Springfield area, Massachusetts

Whimsy & Wonder: A Springfield Weekend for Two

4 stops

2 Days · Couples

Worcester, Massachusetts, Massachusetts

Brick, Steel & Spice: A Worcester Weekend for Two

6 stops

2 Days · Young Families

Plymouth, Massachusetts

Rock, Ship & Sunlit Harbor: A Family Weekend in Plymouth

5 stops

2 Days · Young Families

Worcester, Massachusetts, Massachusetts

Brick, Blossoms, and Elm Park Afternoons: 2 Days in Worcester with Little Ones

4 stops

2 Days · Couples

Concord, Massachusetts

Wildflowers & Wood Smoke: Two Days of Concord's Quiet Romance

6 stops

2 Days · Young Families

Concord, Massachusetts

Little Women, Big Woods: A Family Weekend in Concord

3 stops

2 Days · Teen Families

Pioneer Valley, Massachusetts

Farm Tables & Ivy Halls: A Pioneer Valley Weekend for Food-Curious Families

5 stops

3 Days · Young Families

Boston Metro, Massachusetts

Cobblestones & Small Steps: 3 Days of Revolutionary Boston for Little Legs

6 stops

2 Days · Young Families

Pioneer Valley, Massachusetts

Farm Tables & Riverbank Wanderings: A Slow Family Weekend in the Pioneer Valley

4 stops

2 Days · Couples

Pioneer Valley, Massachusetts

Vines, Views & Valley Light: A Pioneer Valley Escape for Two

4 stops

3 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

Cliffside Light: A Slow Coastal Escape on Martha's Vineyard

4 stops

3 Days · Teen Families

Nantucket (off-season), Massachusetts

Wind, Roses, and Whale Bones: 3 Days in Off-Season Nantucket

4 stops

2 Days · Active Retirees

Cape Cod (off-season), Massachusetts

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

3 stops

3 Days · Teen Families

North Shore (Salem area), Massachusetts

Salted Air & Old Secrets: 3 Days on Salem's Historic Shoreline

5 stops

3 Days · Solo

Nantucket (off-season), Massachusetts

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

6 stops

2 Days · Active Retirees

Nantucket (off-season), Massachusetts

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

3 stops

3 Days · Solo

Cape Cod (off-season), Massachusetts

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

5 stops

3 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

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

5 stops

2 Days · Active Retirees

North Shore (Salem area), Massachusetts

Salt Air & Storied Streets: Two Days in Salem

3 stops

3 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Shores: 3 Days in Off-Season Provincetown

6 stops

3 Days · Solo

North Shore (Salem area), Massachusetts

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

6 stops

2 Days · Young Families

Cape Cod (off-season), Massachusetts

Sand, Sky, and Small Steps: A Family Weekend on the Outer Cape

4 stops

2 Days · Young Families

North Shore (Salem area), Massachusetts

Gables, Ghost Stories & Harbor Light: 2 Days in Salem for Young Families

3 stops

2 Days · Couples

North Shore (Salem area), Massachusetts

Salt Air & Seven Gables: A Slow Salem Weekend for Two

3 stops

2 Days · Young Families

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Coves: 2 Days in Off-Season Martha's Vineyard

3 stops

2 Days · Couples

Nantucket (off-season), Massachusetts

Salt Air & Rose Lanes: A Quiet Nantucket for Two

4 stops

2 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Light: Two Days in Off-Season Aquinnah

3 stops

2 Days · Young Families

Nantucket (off-season), Massachusetts

Rose Lanes & Quiet Shores: A Spring Weekend in Nantucket with Kids

3 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

Showing 60 of 86 — explore all of Massachusetts.