Summer Itineraries in Massachusetts

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

38 itineraries

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

Brick, Park & Piri-Piri: 3 Slow Days in Worcester with Little Ones

3 Days · Young Families

Worcester, Massachusetts, Massachusetts

Brick, Park & Piri-Piri: 3 Slow Days in Worcester with Little Ones

4 stops

Still Water, Small Hands: 4 Days at the Quabbin

4 Days · Young Families

Quabbin Reservoir area, Massachusetts

Still Water, Small Hands: 4 Days at the Quabbin

6 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 & Gabled Shadows: 4 Days on Salem's Historic Shore

4 Days · Couples

North Shore (Salem area), Massachusetts

Salt Air & Gabled Shadows: 4 Days on Salem's Historic Shore

8 stops

Rock, Rope & Grindstone: 3 Slow Days in Plymouth with Little Ones

3 Days · Young Families

Plymouth, Massachusetts

Rock, Rope & Grindstone: 3 Slow Days in Plymouth with Little Ones

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

Cliffside Hours: A Slow Escape to Aquinnah

4 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

Cliffside Hours: A Slow Escape to Aquinnah

5 stops

Salt Air & Slow Hours: 4 Days in Nantucket for Two

4 Days · Couples

Nantucket (off-season), Massachusetts

Salt Air & Slow Hours: 4 Days in Nantucket for Two

6 stops

Dune Light & Salt Air: Four Days Adrift on the Outer Cape

4 Days · Couples

Cape Cod (off-season), Massachusetts

Dune Light & Salt Air: Four Days Adrift on the Outer Cape

8 stops

Whimsy on Chestnut Street: A Family Weekend in Springfield's Quadrangle

3 Days · Young Families

Springfield area, Massachusetts

Whimsy on Chestnut Street: A Family Weekend in Springfield's Quadrangle

4 stops

Little Women & Big Woods: A Family Wander Through Concord

3 Days · Young Families

Concord, Massachusetts

Little Women & Big Woods: A Family Wander Through Concord

4 stops

Still Water, Slow Days: A Quabbin Reservoir Escape for Two

3 Days · Couples

Quabbin Reservoir area, Massachusetts

Still Water, Slow Days: A Quabbin Reservoir Escape for Two

6 stops

Cobblestones & Ice Cream: 4 Days of Little Feet on the Freedom Trail

4 Days · Young Families

Boston Metro, Massachusetts

Cobblestones & Ice Cream: 4 Days of Little Feet on the Freedom Trail

9 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

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