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
24 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
28 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
29 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
26 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
30 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
22 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.
20 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
20 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
20 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
20 itineraries
Massachusetts Itineraries
2 Days · Teen Families
Plymouth, Massachusetts
Rock, Rope, and Rising Tide: Two Days in Plymouth
7 stops
2 Days · Teen Families
Springfield area, Massachusetts
Whimsy and Wonder in the Quadrangle: Two Days in Springfield
5 stops
2 Days · Teen Families
Worcester, Massachusetts, Massachusetts
Brick, Steel & Spice: Two Days in Worcester's Creative Heart
6 stops
2 Days · Teen Families
Concord, Massachusetts
Minutemen, Manuscripts & Mirror Ponds: 2 Days in Concord
5 stops
2 Days · Teen Families
Springfield area, Massachusetts
Whimsy and Wonder in the Quadrangle: 2 Days in Springfield
4 stops
2 Days · Teen Families
Worcester, Massachusetts, Massachusetts
Brick, Steel & Spice: Two Fall Days in Worcester
6 stops
2 Days · Solo
Worcester, Massachusetts, Massachusetts
Brick, Steel & Spice: Two Days Solo in Worcester
6 stops
2 Days · Teen Families
Plymouth, Massachusetts
Stone, Sail & Shoreline: 2 Days in Pilgrim Plymouth
7 stops
2 Days · Solo
Springfield area, Massachusetts
Whimsy and Wonder: Two Days in Springfield's Quadrangle
4 stops
2 Days · Solo
Plymouth, Massachusetts
Stone, Ship, and Sea: Two Days Solo in Plymouth
7 stops
2 Days · Solo
Concord, Massachusetts
Pages and Ponds: A Solo Wander Through Concord
5 stops
2 Days · Teen Families
Concord, Massachusetts
Pages and Ponds: Two Days in Concord
5 stops