Summer Itineraries in Massachusetts

Long daylight hours and peak-season energy — plans built for the busiest, brightest stretch of the year.

76 itineraries

Still Waters: Four Slow Days at the Quabbin Reservoir

4 Days · Active Retirees

Quabbin Reservoir area, Massachusetts

Still Waters: Four Slow Days at the Quabbin Reservoir

6 stops

Still Water, Slow Light: 4 Days at Quabbin Reservoir

4 Days · Couples

Quabbin Reservoir area, Massachusetts

Still Water, Slow Light: 4 Days at Quabbin Reservoir

7 stops

Salt Air & Solitude: 4 Days Alone on Nantucket

4 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Solitude: 4 Days Alone on Nantucket

7 stops

Dune Light & Quiet Tides: A Solo Escape to Provincetown

4 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: A Solo Escape to Provincetown

8 stops

Cliffside Solitude: 4 Days Adrift on Martha's Vineyard

4 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliffside Solitude: 4 Days Adrift on Martha's Vineyard

6 stops

Salt Air & Storied Streets: Four Days on Salem's Historic Waterfront

4 Days · Active Retirees

North Shore (Salem area), Massachusetts

Salt Air & Storied Streets: Four Days on Salem's Historic Waterfront

4 stops

Salt Air & Slow Light: 4 Days in Nantucket

4 Days · Active Retirees

Nantucket (off-season), Massachusetts

Salt Air & Slow Light: 4 Days in Nantucket

5 stops

Dune Light & Gallery Quiet: A Provincetown Retreat

4 Days · Active Retirees

Cape Cod (off-season), Massachusetts

Dune Light & Gallery Quiet: A Provincetown Retreat

6 stops

Cliff Light & Salt Wind: 4 Days on Martha's Vineyard

4 Days · Active Retirees

Martha’s Vineyard (off-season), Massachusetts

Cliff Light & Salt Wind: 4 Days on Martha's Vineyard

6 stops

Rose Lanes & Low Tide: 4 Days in Nantucket with Little Ones

4 Days · Young Families

Nantucket (off-season), Massachusetts

Rose Lanes & Low Tide: 4 Days in Nantucket with Little Ones

6 stops

Dune Light and Little Footprints: 4 Days on the Outer Cape

4 Days · Young Families

Cape Cod (off-season), Massachusetts

Dune Light and Little Footprints: 4 Days on the Outer Cape

6 stops

Gables, Ghosts & Gentle Tides: 4 Days in Salem with Little Ones

4 Days · Young Families

North Shore (Salem area), Massachusetts

Gables, Ghosts & Gentle Tides: 4 Days in Salem with Little Ones

6 stops

Cliffside Wonder: A Slow Family Escape to Aquinnah

4 Days · Young Families

Martha’s Vineyard (off-season), Massachusetts

Cliffside Wonder: A Slow Family Escape to Aquinnah

4 stops

Salt Air & Cobblestones: A Solo Weekend on Nantucket

2 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Cobblestones: A Solo Weekend on 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

Dune Light & Quiet Tides: A Solo Weekend in Provincetown

2 Days · Solo

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: A Solo Weekend in Provincetown

5 stops

Clay, Light, and Salt Wind: Two Days Alone at Aquinnah

2 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Clay, Light, and Salt Wind: Two Days Alone at Aquinnah

4 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 Alone in Salem

2 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Old Secrets: Two Days Alone in Salem

3 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

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

Still Water, Quiet Company: 3 Days Alone at Quabbin

3 Days · Solo

Quabbin Reservoir area, Massachusetts

Still Water, Quiet Company: 3 Days Alone at Quabbin

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

Still Water, Small Feet: Two Days at Quabbin Reservoir

2 Days · Young Families

Quabbin Reservoir area, Massachusetts

Still Water, Small Feet: Two Days at Quabbin Reservoir

4 stops

Water and Silence: A Quabbin Reservoir Escape for Two

2 Days · Couples

Quabbin Reservoir area, Massachusetts

Water and Silence: A Quabbin Reservoir Escape for Two

6 stops

Sand, Silence & Salt Air: 3 Days Alone on the Outer Cape

3 Days · Solo

Cape Cod (off-season), Massachusetts

Sand, Silence & Salt Air: 3 Days Alone on the Outer Cape

6 stops

Cliffside Solitude: 3 Days Alone with Martha's Vineyard's Western Light

3 Days · Solo

Martha’s Vineyard (off-season), Massachusetts

Cliffside Solitude: 3 Days Alone with Martha's Vineyard's Western Light

4 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

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

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

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

Salt Air & Solitude: 3 Days Alone on Nantucket

3 Days · Solo

Nantucket (off-season), Massachusetts

Salt Air & Solitude: 3 Days Alone on Nantucket

4 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

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

Salt Air & Old Secrets: Three Days Solo on Salem's Shore

3 Days · Solo

North Shore (Salem area), Massachusetts

Salt Air & Old Secrets: Three Days Solo on Salem's Shore

4 stops

Sand, Salt & Small Footprints: 2 Days in Provincetown

2 Days · Young Families

Cape Cod (off-season), Massachusetts

Sand, Salt & Small Footprints: 2 Days in Provincetown

4 stops

Roses, Whales, and Salt Air: Two Days in Nantucket

2 Days · Couples

Nantucket (off-season), Massachusetts

Roses, Whales, and Salt Air: Two Days in Nantucket

4 stops

Dunes, Light, and Quiet Tides: Two Days in Provincetown

2 Days · Couples

Cape Cod (off-season), Massachusetts

Dunes, Light, and Quiet Tides: Two Days in Provincetown

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

Salted Air & Gabled Secrets: Two Days on Salem's Historic Shore

2 Days · Couples

North Shore (Salem area), Massachusetts

Salted Air & Gabled Secrets: Two Days on Salem's Historic Shore

3 stops

Clay Cliffs & Quiet Tides: A Family Weekend in Aquinnah

2 Days · Young Families

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Tides: A Family Weekend in Aquinnah

3 stops

Salem, Slowed Down: Gables, Ghosts, and Gentle Days for Little Explorers

2 Days · Young Families

North Shore (Salem area), Massachusetts

Salem, Slowed Down: Gables, Ghosts, and Gentle Days for Little Explorers

3 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

Sandy Toes & Rose Lanes: 2 Summer Days in Nantucket with Little Ones

2 Days · Young Families

Nantucket (off-season), Massachusetts

Sandy Toes & Rose Lanes: 2 Summer Days in Nantucket with Little Ones

4 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 Tides: Two Days in Aquinnah

2 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Tides: Two Days in Aquinnah

4 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

Salt Air & Seven Gables: A North Shore Romance

3 Days · Couples

North Shore (Salem area), Massachusetts

Salt Air & Seven Gables: A North Shore Romance

5 stops

Sandy Toes & Slow Mornings: 3 Days in Off-Season Cape Cod

3 Days · Young Families

Cape Cod (off-season), Massachusetts

Sandy Toes & Slow Mornings: 3 Days in Off-Season Cape Cod

5 stops

Dune Light & Quiet Tides: 3 Days in Provincetown

3 Days · Couples

Cape Cod (off-season), Massachusetts

Dune Light & Quiet Tides: 3 Days in Provincetown

6 stops

Salt Air & Slow Light: 3 Days in Nantucket for Two

3 Days · Couples

Nantucket (off-season), Massachusetts

Salt Air & Slow Light: 3 Days in Nantucket for Two

5 stops

Cliffside Hours: A Gentle Family Escape to Aquinnah

3 Days · Young Families

Martha’s Vineyard (off-season), Massachusetts

Cliffside Hours: A Gentle Family Escape to Aquinnah

4 stops

Sand Between Their Toes: 3 Days in Nantucket for Little Explorers

3 Days · Young Families

Nantucket (off-season), Massachusetts

Sand Between Their Toes: 3 Days in Nantucket for Little Explorers

5 stops

Clay Cliffs & Quiet Light: 3 Days in Martha's Vineyard

3 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Light: 3 Days in Martha's Vineyard

4 stops

Gables, Gulls & Gentle History: 3 Days in Salem with Little Ones

3 Days · Young Families

North Shore (Salem area), Massachusetts

Gables, Gulls & Gentle History: 3 Days in Salem with Little Ones

3 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

Still Water Days: A Family Weekend at Quabbin Reservoir

3 Days · Young Families

Quabbin Reservoir area, Massachusetts

Still Water Days: A Family Weekend at Quabbin Reservoir

4 stops

Showing 60 of 76 — explore all of Massachusetts.

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