4 Days · Active Retirees
Cape Cod (off-season), Massachusetts
Dune Light & Gallery Quiet: A Provincetown Retreat
6 stops
4 Days · Active Retirees
Martha’s Vineyard (off-season), Massachusetts
Cliff Light & Salt Wind: 4 Days on Martha's Vineyard
6 stops
4 Days · Young Families
Cape Cod (off-season), Massachusetts
Dunes, Driftwood & Downtime: 4 Days in Off-Season Provincetown
5 stops
4 Days · Young Families
Nantucket (off-season), Massachusetts
Rose Lanes & Quiet Tides: 4 Days in Off-Season Nantucket
6 stops
4 Days · Young Families
Martha’s Vineyard (off-season), Massachusetts
Cliffside Quiet: A Family Slow-Down on Martha's Vineyard
5 stops
4 Days · Couples
Nantucket (off-season), Massachusetts
Salt Air & Winter Light: 4 Days of Off-Season Nantucket for Two
6 stops
4 Days · Couples
North Shore (Salem area), Massachusetts
Salt Air & Storied Streets: Four Days on Salem's North Shore
4 stops
4 Days · Young Families
Nantucket (off-season), Massachusetts
Rose Lanes & Low Tide: 4 Days in Nantucket with Little Ones
6 stops
4 Days · Young Families
Cape Cod (off-season), Massachusetts
Dune Light and Little Footprints: 4 Days on the Outer Cape
6 stops
4 Days · Young Families
North Shore (Salem area), Massachusetts
Gables, Ghosts & Gentle Tides: 4 Days in Salem with Little Ones
6 stops
4 Days · Couples
Cape Cod (off-season), Massachusetts
Dune Light & Quiet Tides: 4 Days in Off-Season Provincetown
7 stops
4 Days · Couples
Martha’s Vineyard (off-season), Massachusetts
Cliff Light & Quiet Tides: 4 Days on Martha's Vineyard
6 stops
4 Days · Young Families
Martha’s Vineyard (off-season), Massachusetts
Cliffside Wonder: A Slow Family Escape to Aquinnah
4 stops
2 Days · Teen Families
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Tides: Two Days Off-Season in Aquinnah
4 stops
2 Days · Solo
North Shore (Salem area), Massachusetts
Salt Air & Shadowed Streets: Two Days on Salem's Cobblestones
5 stops
2 Days · Solo
Martha’s Vineyard (off-season), Massachusetts
Cliffs, Quiet, and Clay-Red Light: 2 Days Alone on Martha's Vineyard
4 stops
2 Days · Solo
Cape Cod (off-season), Massachusetts
Dune Light & Quiet Tides: Two Days Alone on the Outer Cape
5 stops
2 Days · Teen Families
North Shore (Salem area), Massachusetts
Salt Air & Séance Bells: 2 Days in Salem
3 stops
2 Days · Solo
Nantucket (off-season), Massachusetts
Roses, Fog, and Salt Air: A Solo Escape to Off-Season Nantucket
4 stops
2 Days · Teen Families
Cape Cod (off-season), Massachusetts
Dunes, Gray Light & Wild Shore: 2 Days in Off-Season Provincetown
4 stops
2 Days · Teen Families
Nantucket (off-season), Massachusetts
Roses, Wind, and Whale Bones: 2 Days in Off-Season Nantucket
4 stops
2 Days · Solo
Nantucket (off-season), Massachusetts
Salt Air & Cobblestones: A Solo Weekend on Nantucket
4 stops
2 Days · Teen Families
Nantucket (off-season), Massachusetts
Roses, Sand, and Salt Air: 2 Days in Nantucket for Families
4 stops
2 Days · Teen Families
Cape Cod (off-season), Massachusetts
Dunes, Light, and Salt Wind: 2 Days on the Outer Cape
5 stops
2 Days · Solo
Cape Cod (off-season), Massachusetts
Dune Light & Quiet Tides: A Solo Weekend in Provincetown
5 stops
2 Days · Solo
Martha’s Vineyard (off-season), Massachusetts
Clay, Light, and Salt Wind: Two Days Alone at Aquinnah
4 stops
2 Days · Teen Families
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Salt Wind: 2 Days in Aquinnah with Teens
4 stops
2 Days · Solo
North Shore (Salem area), Massachusetts
Salt Air & Old Secrets: Two Days Alone in Salem
3 stops
2 Days · Teen Families
North Shore (Salem area), Massachusetts
Salt Air & Old Secrets: Two Days on Salem's Historic North Shore
3 stops
3 Days · Teen Families
Martha’s Vineyard (off-season), Massachusetts
Cliffside Light: A Slow Coastal Escape on Martha's Vineyard
4 stops
3 Days · Teen Families
Nantucket (off-season), Massachusetts
Wind, Roses, and Whale Bones: 3 Days in Off-Season Nantucket
4 stops
2 Days · Active Retirees
Cape Cod (off-season), Massachusetts
Dune Light and Gallery Quiet: Two Days on the Outer Cape
3 stops
3 Days · Teen Families
North Shore (Salem area), Massachusetts
Salted Air & Old Secrets: 3 Days on Salem's Historic Shoreline
5 stops
3 Days · Solo
Nantucket (off-season), Massachusetts
Salt Air & Empty Shores: 3 Days Alone on Off-Season Nantucket
6 stops
2 Days · Active Retirees
Nantucket (off-season), Massachusetts
Salt Air & Slow Roses: Two Days in Off-Season Nantucket
3 stops
3 Days · Solo
Cape Cod (off-season), Massachusetts
Dune Light & Quiet Company: 3 Days Solo on the Outer Cape
5 stops
3 Days · Solo
Martha’s Vineyard (off-season), Massachusetts
Cliff Light & Quiet Roads: A Solo Off-Season Escape to Martha's Vineyard
5 stops
2 Days · Active Retirees
North Shore (Salem area), Massachusetts
Salt Air & Storied Streets: Two Days in Salem
3 stops
3 Days · Teen Families
Cape Cod (off-season), Massachusetts
Dune Light & Quiet Shores: 3 Days in Off-Season Provincetown
6 stops
3 Days · Solo
North Shore (Salem area), Massachusetts
Salt Air & Shadowed Streets: Three Days Solo on the North Shore
6 stops
3 Days · Solo
Cape Cod (off-season), Massachusetts
Sand, Silence & Salt Air: 3 Days Alone on the Outer Cape
6 stops
3 Days · Solo
Martha’s Vineyard (off-season), Massachusetts
Cliffside Solitude: 3 Days Alone with Martha's Vineyard's Western Light
4 stops
2 Days · Active Retirees
Martha’s Vineyard (off-season), Massachusetts
Cliffside Light: Two Slow Days at Martha's Vineyard's Western Edge
4 stops
3 Days · Teen Families
Nantucket (off-season), Massachusetts
Rose Lanes & Restless Tides: 3 Days in Nantucket for Families
4 stops
2 Days · Active Retirees
Cape Cod (off-season), Massachusetts
Dune Light & Gallery Quiet: Two Days on the Outer Cape
3 stops
2 Days · Active Retirees
North Shore (Salem area), Massachusetts
Salted Gables: Two Slow Days in Historic Salem
3 stops
3 Days · Teen Families
Martha’s Vineyard (off-season), Massachusetts
Cliffs, Light, and Salt Air: 3 Days on Martha's Vineyard
5 stops
3 Days · Solo
Nantucket (off-season), Massachusetts
Salt Air & Solitude: 3 Days Alone on Nantucket
4 stops
3 Days · Teen Families
Cape Cod (off-season), Massachusetts
Dune Light and Salt Air: 3 Days on the Outer Cape
8 stops
3 Days · Teen Families
North Shore (Salem area), Massachusetts
Salted Air & Old Secrets: 3 Days on Salem's Historic Shore
5 stops
2 Days · Active Retirees
Nantucket (off-season), Massachusetts
Roses, Whales, and Slow Tides: Two Days in Nantucket
4 stops
3 Days · Solo
North Shore (Salem area), Massachusetts
Salt Air & Old Secrets: Three Days Solo on Salem's Shore
4 stops
2 Days · Young Families
Cape Cod (off-season), Massachusetts
Sand, Sky, and Small Steps: A Family Weekend on the Outer Cape
4 stops
2 Days · Young Families
North Shore (Salem area), Massachusetts
Gables, Ghost Stories & Harbor Light: 2 Days in Salem for Young Families
3 stops
2 Days · Couples
North Shore (Salem area), Massachusetts
Salt Air & Seven Gables: A Slow Salem Weekend for Two
3 stops
2 Days · Young Families
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Coves: 2 Days in Off-Season Martha's Vineyard
3 stops
2 Days · Couples
Nantucket (off-season), Massachusetts
Salt Air & Rose Lanes: A Quiet Nantucket for Two
4 stops
2 Days · Couples
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Light: Two Days in Off-Season Aquinnah
3 stops
2 Days · Young Families
Nantucket (off-season), Massachusetts
Rose Lanes & Quiet Shores: A Spring Weekend in Nantucket with Kids
3 stops
2 Days · Young Families
Cape Cod (off-season), Massachusetts
Sand, Salt & Small Footprints: 2 Days in Provincetown
4 stops
Showing 60 of 97 — explore all of Massachusetts.
Massachusetts coastal destinations offer rich possibilities for beach getaways, whether traveling during off-season months or planning a quiet escape. This collection features 12 itineraries across four prime locations: Cape Cod, Martha's Vineyard, Nantucket, and the North Shore near Salem. Visitors can choose from 4-day immersive experiences and shorter 3-day trips tailored to different travelers—families with children, teenagers, couples, and those seeking solitude. Each itinerary weaves together the region's signature elements: windswept dunes, historic architecture, coastal light, and the restorative rhythm of salt air and unhurried hours.
Frequently Asked Questions
What length itineraries are available on this page?
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The page offers both 4-day and 3-day itineraries, allowing travelers to choose based on their schedule and travel style.
Which destinations are covered in these itineraries?
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Four destinations are featured: Cape Cod, Martha's Vineyard, Nantucket, and the North Shore (Salem area), with itineraries designed for off-season travel.
Are there itineraries designed for specific types of travelers?
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Yes. The collection includes itineraries tailored for family groups, teen families, couples, and solo or slow-travel seekers exploring these coastal regions.
What themes appear across these itineraries?
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Common themes include dunes and coastal light, historic architecture and local history, salt air, whales and wildlife, and unhurried time in quieter settings.
More Collections
Or see Beach Getaways nationwide or browse every Massachusetts destination.