Families with Teens Itineraries in Massachusetts

Faster pacing, bigger thrills, and enough independence built in to keep teenagers engaged from breakfast to lights-out.

50 itineraries

Still Water, Deep Woods: 4 Days at the Quabbin Reservoir

4 Days · Teen Families

Quabbin Reservoir area, Massachusetts

Still Water, Deep Woods: 4 Days at the Quabbin Reservoir

9 stops

Drowned Valleys & Still Water: 4 Days at Quabbin Reservoir

4 Days · Teen Families

Quabbin Reservoir area, Massachusetts

Drowned Valleys & Still Water: 4 Days at Quabbin Reservoir

9 stops

Rock, Rope, and Rising Tide: Two Days in Plymouth

2 Days · Teen Families

Plymouth, Massachusetts

Rock, Rope, and Rising Tide: Two Days in Plymouth

7 stops

Whimsy and Wonder in the Quadrangle: Two Days in Springfield

2 Days · Teen Families

Springfield area, Massachusetts

Whimsy and Wonder in the Quadrangle: Two Days in Springfield

5 stops

Brick, Steel & Spice: Two Days in Worcester's Creative Heart

2 Days · Teen Families

Worcester, Massachusetts, Massachusetts

Brick, Steel & Spice: Two Days in Worcester's Creative Heart

6 stops

Minutemen, Manuscripts & Mirror Ponds: 2 Days in Concord

2 Days · Teen Families

Concord, Massachusetts

Minutemen, Manuscripts & Mirror Ponds: 2 Days in Concord

5 stops

Whimsy and Wonder in the Quadrangle: 2 Days in Springfield

2 Days · Teen Families

Springfield area, Massachusetts

Whimsy and Wonder in the Quadrangle: 2 Days in Springfield

4 stops

Brick, Steel & Spice: Two Fall Days in Worcester

2 Days · Teen Families

Worcester, Massachusetts, Massachusetts

Brick, Steel & Spice: Two Fall Days in Worcester

6 stops

Stone, Sail & Shoreline: 2 Days in Pilgrim Plymouth

2 Days · Teen Families

Plymouth, Massachusetts

Stone, Sail & Shoreline: 2 Days in Pilgrim Plymouth

7 stops

Pages and Ponds: Two Days in Concord

2 Days · Teen Families

Concord, Massachusetts

Pages and Ponds: Two Days in Concord

5 stops

Salt Air & Widow's Walks: 4 Days in Off-Season Nantucket

4 Days · Teen Families

Nantucket (off-season), Massachusetts

Salt Air & Widow's Walks: 4 Days in Off-Season Nantucket

8 stops

Salt Air & Shadowed Streets: 4 Days on Salem's North Shore

4 Days · Teen Families

North Shore (Salem area), Massachusetts

Salt Air & Shadowed Streets: 4 Days on Salem's North Shore

6 stops

Dune Light & Salt Wind: 4 Days in Off-Season Provincetown

4 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dune Light & Salt Wind: 4 Days in Off-Season Provincetown

6 stops

Still Water, Wide Sky: A Fall Weekend at Quabbin Reservoir

2 Days · Teen Families

Quabbin Reservoir area, Massachusetts

Still Water, Wide Sky: A Fall Weekend at Quabbin Reservoir

6 stops

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

2 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

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

4 stops

Salt Air & Séance Bells: 2 Days in Salem

2 Days · Teen Families

North Shore (Salem area), Massachusetts

Salt Air & Séance Bells: 2 Days in Salem

3 stops

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

2 Days · Teen Families

Cape Cod (off-season), Massachusetts

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

4 stops

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

2 Days · Teen Families

Nantucket (off-season), Massachusetts

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

4 stops

Roses, Sand, and Salt Air: 2 Days in Nantucket for Families

2 Days · Teen Families

Nantucket (off-season), Massachusetts

Roses, Sand, and Salt Air: 2 Days in Nantucket for Families

4 stops

Dunes, Light, and Salt Wind: 2 Days on the Outer Cape

2 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dunes, Light, and Salt Wind: 2 Days on the Outer Cape

5 stops

Clay Cliffs & Salt Wind: 2 Days in Aquinnah with Teens

2 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Salt Wind: 2 Days in Aquinnah with Teens

4 stops

Salt Air & Old Secrets: Two Days on Salem's Historic North Shore

2 Days · Teen Families

North Shore (Salem area), Massachusetts

Salt Air & Old Secrets: Two Days on Salem's Historic North Shore

3 stops

Brick, Blade & Berbere: Three Days in Worcester

3 Days · Teen Families

Worcester, Massachusetts, Massachusetts

Brick, Blade & Berbere: Three Days in Worcester

9 stops

Whimsy & Wonder: A Springfield Family Weekend in the Quadrangle

3 Days · Teen Families

Springfield area, Massachusetts

Whimsy & Wonder: A Springfield Family Weekend in the Quadrangle

6 stops

Brick, Blade & Berbere: A Worcester Weekend for the Whole Family

3 Days · Teen Families

Worcester, Massachusetts, Massachusetts

Brick, Blade & Berbere: A Worcester Weekend for the Whole Family

8 stops

Rock, Rope & Rising Tide: 3 Days in Plymouth

3 Days · Teen Families

Plymouth, Massachusetts

Rock, Rope & Rising Tide: 3 Days in Plymouth

10 stops

Little Women, Big Ideas: A Concord Family Weekend

3 Days · Teen Families

Concord, Massachusetts

Little Women, Big Ideas: A Concord Family Weekend

8 stops

Whimsy and Wonder: 3 Days in Springfield's Quadrangle

3 Days · Teen Families

Springfield area, Massachusetts

Whimsy and Wonder: 3 Days in Springfield's Quadrangle

4 stops

Revolution, Reflection & Red Leaves: 3 Days in Concord

3 Days · Teen Families

Concord, Massachusetts

Revolution, Reflection & Red Leaves: 3 Days in Concord

6 stops

Rock, Rope, and Harbor Light: 3 Days in Plymouth

3 Days · Teen Families

Plymouth, Massachusetts

Rock, Rope, and Harbor Light: 3 Days in Plymouth

8 stops

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

2 Days · Teen Families

Pioneer Valley, Massachusetts

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

5 stops

Harvest Table & Ridgeline Light: 2 Days in Pioneer Valley

2 Days · Teen Families

Pioneer Valley, Massachusetts

Harvest Table & Ridgeline Light: 2 Days in Pioneer Valley

4 stops

Water, Woods, and Wide-Open Sky: 3 Days at Quabbin Reservoir

3 Days · Teen Families

Quabbin Reservoir area, Massachusetts

Water, Woods, and Wide-Open Sky: 3 Days at Quabbin Reservoir

6 stops

Deep Water, Old Towns: Three Days at Quabbin

3 Days · Teen Families

Quabbin Reservoir area, Massachusetts

Deep Water, Old Towns: Three Days at Quabbin

7 stops

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

3 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

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

4 stops

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

3 Days · Teen Families

Nantucket (off-season), Massachusetts

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

4 stops

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

3 Days · Teen Families

North Shore (Salem area), Massachusetts

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

5 stops

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

3 Days · Teen Families

Cape Cod (off-season), Massachusetts

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

6 stops

Rose Lanes & Restless Tides: 3 Days in Nantucket for Families

3 Days · Teen Families

Nantucket (off-season), Massachusetts

Rose Lanes & Restless Tides: 3 Days in Nantucket for Families

4 stops

Cliffs, Light, and Salt Air: 3 Days on Martha's Vineyard

3 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

Cliffs, Light, and Salt Air: 3 Days on Martha's Vineyard

5 stops

Dune Light and Salt Air: 3 Days on the Outer Cape

3 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dune Light and Salt Air: 3 Days on the Outer Cape

8 stops

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

3 Days · Teen Families

North Shore (Salem area), Massachusetts

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

5 stops

Dunes, Light & Salt Air: A Family Escape to Provincetown

4 Days · Teen Families

Cape Cod (off-season), Massachusetts

Dunes, Light & Salt Air: A Family Escape to Provincetown

8 stops

Clay Cliffs & Coastal Light: 4 Days in Martha's Vineyard

4 Days · Teen Families

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Coastal Light: 4 Days in Martha's Vineyard

6 stops

Salt Air & Shadowed History: 4 Days on the North Shore

4 Days · Teen Families

North Shore (Salem area), Massachusetts

Salt Air & Shadowed History: 4 Days on the North Shore

6 stops

Salt Air & Rose Lanes: 4 Days in Nantucket for Teen Families

4 Days · Teen Families

Nantucket (off-season), Massachusetts

Salt Air & Rose Lanes: 4 Days in Nantucket for Teen Families

8 stops

Cobblestones, Tea Parties & Midnight Rides: 3 Days on Boston's Freedom Trail

3 Days · Teen Families

Boston Metro, Massachusetts

Cobblestones, Tea Parties & Midnight Rides: 3 Days on Boston's Freedom Trail

8 stops

Cobblestones & Revolution: 2 Days Through Boston's Freedom Trail

2 Days · Teen Families

Boston Metro, Massachusetts

Cobblestones & Revolution: 2 Days Through Boston's Freedom Trail

6 stops

Cobblestones & Candlelight: Two Days on Boston's Freedom Trail

2 Days · Teen Families

Boston Metro, Massachusetts

Cobblestones & Candlelight: Two Days on Boston's Freedom Trail

6 stops

Cobblestones & Candlelight: 3 Days of Revolution in Boston

3 Days · Teen Families

Boston Metro, Massachusetts

Cobblestones & Candlelight: 3 Days of Revolution in Boston

9 stops

More Collections

We use cookies to improve your experience and analyze site usage. Essential cookies are always active. You can customize your preferences or accept all cookies. Cookie Policy