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
3 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
6 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
10 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
10 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
10 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
10 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
5 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.
4 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
4 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
4 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
4 itineraries
Massachusetts Itineraries
2 Days · Young Families
Cape Cod (off-season), Massachusetts
Sand, Salt & Small Footprints: 2 Days in Provincetown
4 stops
2 Days · Couples
Nantucket (off-season), Massachusetts
Roses, Whales, and Salt Air: Two Days in Nantucket
4 stops
2 Days · Couples
Cape Cod (off-season), Massachusetts
Dunes, Light, and Quiet Tides: Two Days in Provincetown
4 stops
3 Days · Active Retirees
Cape Cod (off-season), Massachusetts
Dune Light & Gallery Quiet: 3 Days at the Cape's Outer Edge
4 stops
2 Days · Couples
North Shore (Salem area), Massachusetts
Salted Air & Gabled Secrets: Two Days on Salem's Historic Shore
3 stops
2 Days · Young Families
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Tides: A Family Weekend in Aquinnah
3 stops
2 Days · Young Families
North Shore (Salem area), Massachusetts
Salem, Slowed Down: Gables, Ghosts, and Gentle Days for Little Explorers
3 stops
3 Days · Active Retirees
Nantucket (off-season), Massachusetts
Rose Lanes & Salt Air: 3 Days in Nantucket
6 stops
2 Days · Young Families
Nantucket (off-season), Massachusetts
Sandy Toes & Rose Lanes: 2 Summer Days in Nantucket with Little Ones
4 stops
3 Days · Active Retirees
North Shore (Salem area), Massachusetts
Salt Air & Old Stories: Three Days on Salem's Cobblestones
3 stops
2 Days · Couples
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Tides: Two Days in Aquinnah
4 stops
3 Days · Active Retirees
Martha’s Vineyard (off-season), Massachusetts
Clay Cliffs & Quiet Light: A Slow Western Escape on Martha's Vineyard
4 stops