Couples Itineraries in Massachusetts

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

54 itineraries

Still Water, Turning Leaves: Four Days at Quabbin Reservoir

4 Days · Couples

Quabbin Reservoir area, Massachusetts

Still Water, Turning Leaves: Four Days at Quabbin Reservoir

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

4 Days · Couples

Nantucket (off-season), Massachusetts

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

6 stops

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

4 Days · Couples

North Shore (Salem area), Massachusetts

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

4 stops

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

4 Days · Couples

Cape Cod (off-season), Massachusetts

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

7 stops

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

4 Days · Couples

Martha’s Vineyard (off-season), Massachusetts

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

6 stops

Rock, Sail & Harbor Light: Two Days in Plymouth

2 Days · Couples

Plymouth, Massachusetts

Rock, Sail & Harbor Light: Two Days in Plymouth

6 stops

Whimsy & Wonder: A Springfield Weekend for Two

2 Days · Couples

Springfield area, Massachusetts

Whimsy & Wonder: A Springfield Weekend for Two

4 stops

Brick, Steel & Spice: A Worcester Weekend for Two

2 Days · Couples

Worcester, Massachusetts, Massachusetts

Brick, Steel & Spice: A Worcester Weekend for Two

6 stops

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

2 Days · Couples

Concord, Massachusetts

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

6 stops

Brick, Steel & Slow Suppers: A Worcester Weekend for Two

2 Days · Couples

Worcester, Massachusetts, Massachusetts

Brick, Steel & Slow Suppers: A Worcester Weekend for Two

6 stops

Whimsy and Wonder: A Slow Fall Weekend in Springfield

2 Days · Couples

Springfield area, Massachusetts

Whimsy and Wonder: A Slow Fall Weekend in Springfield

4 stops

Rock, Rope & Harbor Light: Two Days in Plymouth

2 Days · Couples

Plymouth, Massachusetts

Rock, Rope & Harbor Light: Two Days in Plymouth

6 stops

Falling Leaves & Transcendent Thoughts: Two Days in Concord

2 Days · Couples

Concord, Massachusetts

Falling Leaves & Transcendent Thoughts: Two Days in Concord

5 stops

Brick, Bronze & Autumn Light: Three Days in Worcester

3 Days · Couples

Worcester, Massachusetts, Massachusetts

Brick, Bronze & Autumn Light: Three Days in Worcester

8 stops

Whimsy & Wonder: A Springfield Weekend for Two

3 Days · Couples

Springfield area, Massachusetts

Whimsy & Wonder: A Springfield Weekend for Two

7 stops

Rock, Rope Rigging & Harbor Light: 3 Days in Plymouth

3 Days · Couples

Plymouth, Massachusetts

Rock, Rope Rigging & Harbor Light: 3 Days in Plymouth

9 stops

Falling Leaves & Transcendental Light: 3 Days in Concord

3 Days · Couples

Concord, Massachusetts

Falling Leaves & Transcendental Light: 3 Days in Concord

9 stops

Water and Silence: A Quabbin Weekend for Two

2 Days · Couples

Quabbin Reservoir area, Massachusetts

Water and Silence: A Quabbin Weekend for Two

5 stops

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

2 Days · Couples

Pioneer Valley, Massachusetts

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

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

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: 4 Days Along Boston's Freedom Trail

4 Days · Couples

Boston Metro, Massachusetts

Cobblestones & Candlelight: 4 Days Along Boston's Freedom Trail

9 stops

Cobblestones & Candlelight: 4 Days in Revolutionary Boston

4 Days · Couples

Boston Metro, Massachusetts

Cobblestones & Candlelight: 4 Days in Revolutionary Boston

11 stops

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

2 Days · Couples

Boston Metro, Massachusetts

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

7 stops

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

2 Days · Couples

Boston Metro, Massachusetts

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

7 stops

Cobblestones & Candlelight: A Boston Revolution for Two

3 Days · Couples

Boston Metro, Massachusetts

Cobblestones & Candlelight: A Boston Revolution for Two

8 stops

Cobblestones & Candlelight: A Boston Autumn for Two

3 Days · Couples

Boston Metro, Massachusetts

Cobblestones & Candlelight: A Boston Autumn for Two

9 stops

Cobblestones & Candlelight: 5 Days of Revolutionary Romance in Boston

5 Days · Couples

Boston Metro, Massachusetts

Cobblestones & Candlelight: 5 Days of Revolutionary Romance in Boston

11 stops

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