Sample Itineraries

Massachusetts is a fun place to explore. Whether you’re here for a week, a day or even 1/2 a day. Click the links below to see 1 day and 1/2 day itineraries for the major regions of the state.

When visiting Massachusetts be sure the towns of the Berkshires are on your itinerary or else you will miss out on a chance to experience the rich culture of museums, historic sites, performing arts and outdoor adventures.

Berkshires/Western Mass – Full Day

Berkshires/Western Mass – Half Day

A city steeped in old-world ambience or a bustling, cosmopolitan urban center? Boston is both. A strikingly contemporary suspension bridge at the entrance to the city symbolizes the new; the nearby Paul Revere House stands as a testament to Boston’s revolutionary past. Add to the mix: great art museums, lively sidewalk cafes; and sophisticated dining and shopping.

Boston – Full Day

Boston – Half Day

From the exciting city of Boston, head south to beautiful Cape Cod, known for its stunning seascapes, cultural attractions and tranquil lifestyle.

Cape Cod – Full Day

Cape Cod – Half Day

Central Massachusetts has it all, from quaint country villages to old brick factory towns, and from rolling hills to sprawling farms and meadows, and from folk art to dramatic natural views to world-class outdoor museums. Everyone is sure to find something to pique their interest here

Central Mass – Full Day

Central Mass – Half Day

Just thirty-minutes north and west of Boston lies the Greater Merrimack Valley, a region rich in history and natural beauty and home to the historic communities of Lowell, Lexington and Concord. Visit the region where freedom began.

Merrimack Valley/North Central Mass – Full Day

Merrimack Valley/North Central Mass – Half Day

If you want to experience picture-book New England, all you need to do is travel along the Mohawk Trail, Route 2 running east to west in the far northwestern part of the state. The Trail connects quaint little villages that dot the northwestern border of Massachusetts.

Mohawk Trail – Full Day

Mohawk Trail – Half Day

Where else can you visit a living-history museum that recreates life in 1627, go on a whale-watching cruise and taste some of the region’s best wine? It has to be south of Boston, where Massachusetts is alive with history, beaches and quirky little surprises.

Plymouth County/Southeastern Mass – Full Day

Plymouth County/Southeastern Mass – Half Day

In the Pioneer Valley, you can explore the vibrant nightlife of big cities like Springfield, the lively college towns of Northampton and Amherst and traditional New England towns and historic villages. Along the way, you’ll discover fun-filled attractions and distinctive distractions so varied, so enticing, that one visit here just won’t be enough.

Springfield/Pioneer Valley – Full Day

Springfield/Pioneer Valley – Half Day