Where to Go in Massachusetts
Wine Culinary
Berkshires (North/South)
Nestled between two river valleys in western Massachusetts, the Berkshires evoke a timeless New England charm where rolling forested hills meet vibrant cultural institutions and pristine natural wonde
2 itineraries
Wine Culinary
Pioneer Valley
Nestled along the Connecticut River in western Massachusetts, the Pioneer Valley is a region where New England's intellectual heritage meets pastoral beauty and small-town charm. Historic college town
10 itineraries
Lake Cabin
Quabbin Reservoir area
Nestled in central Massachusetts, the Quabbin Reservoir is a sprawling inland sea that feels worlds away from the urban bustle it quietly sustains. This massive body of water, formed by the damming of
17 itineraries
Beach Coastal
North Shore (Salem area)
The North Shore of Massachusetts is where American history whispers from every weathered doorway and cobblestone street. Salem's dark chapters of witch trials and maritime mystique blend seamlessly wi
24 itineraries
Beach Coastal
Cape Cod (off-season)
Cape Cod in the off-season reveals a quieter, more authentic New England character—windswept dunes meet moody Atlantic skies, and the crowds that choke summer beaches have vanished. Provincetown Dunes
24 itineraries
Beach Coastal
Martha’s Vineyard (off-season)
Martha's Vineyard in the off-season is a quietly magical escape where windswept moors meet dramatic coastal cliffs and the summer crowds dissolve into memory. The island transforms into a contemplativ
24 itineraries
Beach Coastal
Nantucket (off-season)
Nantucket in the off-season is a place of windswept beauty and quiet contemplation—a small New England island that sheds its summer crowds and reveals its true character. Siasconset Beach, with its we
25 itineraries
Metro
Boston Metro
Boston is a living museum where American history breathes on every cobblestone street and in every brick facade. This compact, walkable city pulses with the energy of world-class universities, innovat
16 itineraries
Character City
Springfield area
Springfield, Massachusetts, is a vibrant cultural hub in the heart of Western Massachusetts, where American literary history comes alive through whimsical museums and thoughtfully curated collections.
17 itineraries
Character City
Concord
Concord is where American history breathes through tree-lined streets and well-preserved Colonial architecture. This Massachusetts town cradled the spark of Revolution on April 19, 1775, and today inv
16 itineraries
Character City
Plymouth
Plymouth is where American history crystallizes into tangible experience—a waterfront town where the Mayflower's arrival in 1620 feels both distant and intimately present. Walking these colonial stree
16 itineraries
Character City
Worcester, Massachusetts
Worcester, the beating heart of Massachusetts, pulses with creative energy and industrial heritage wrapped in genuine New England character. This often-overlooked city offers visitors a refreshing alt
17 itineraries
Massachusetts Itineraries
2 Days · Active Retirees
Quabbin Reservoir area, Massachusetts
Still Waters: A Fall Weekend at Quabbin Reservoir
4 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