Couples Itineraries in Massachusetts

Slow mornings, golden-hour views, and evenings worth dressing up for — trips paced for two.

27 itineraries

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

2 Days · Couples

North Shore (Salem area), Massachusetts

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

3 stops

Salt Air & Rose Lanes: A Quiet Nantucket for Two

2 Days · Couples

Nantucket (off-season), Massachusetts

Salt Air & Rose Lanes: A Quiet Nantucket for Two

4 stops

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

2 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

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

3 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

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: Two Days in Aquinnah

2 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

Clay Cliffs & Quiet Tides: Two Days in Aquinnah

4 stops

Salted Air & Old Doorways: 3 Days on the North Shore

3 Days · Couples

North Shore (Salem area), Massachusetts

Salted Air & Old Doorways: 3 Days on the North Shore

5 stops

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

3 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

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

4 stops

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

3 Days · Couples

Cape Cod (off-season), Massachusetts

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

5 stops

Salt Air & Slow Light: 3 Days in Off-Season Nantucket

3 Days · Couples

Nantucket (off-season), Massachusetts

Salt Air & Slow Light: 3 Days in Off-Season Nantucket

6 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

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

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

Still Water, Slow Light: 3 Days at Quabbin Reservoir

3 Days · Couples

Quabbin Reservoir area, Massachusetts

Still Water, Slow Light: 3 Days at Quabbin Reservoir

7 stops

Amber Leaves & Long Tables: Two Slow Days in the Pioneer Valley

2 Days · Couples

Pioneer Valley, Massachusetts

Amber Leaves & Long Tables: Two Slow Days in the Pioneer Valley

4 stops

Brick, Steel & Spice: A Slow Worcester Weekend

3 Days · Couples

Worcester, Massachusetts, Massachusetts

Brick, Steel & Spice: A Slow Worcester Weekend

9 stops

Whimsy and Wonder: A Quadrangle Escape in Springfield

3 Days · Couples

Springfield area, Massachusetts

Whimsy and Wonder: A Quadrangle Escape in Springfield

3 stops

Salt Air & Slate Stones: A Plymouth Weekend for Two

3 Days · Couples

Plymouth, Massachusetts

Salt Air & Slate Stones: A Plymouth Weekend for Two

10 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

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

Wildflowers & Wood Smoke: 3 Days of Romance in Concord

3 Days · Couples

Concord, Massachusetts

Wildflowers & Wood Smoke: 3 Days of Romance in Concord

6 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 & Candlelight: A Boston Autumn for Two

3 Days · Couples

Boston Metro, Massachusetts

Cobblestones & Candlelight: A Boston Autumn for Two

9 stops

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