See Massachusetts’s main highlights while learning about its whale-related history. Travel inland to the beautiful Berkshires where Moby Dick author Herman Melville lived, and learn about the legacy of the rightly abandoned whaling industry. You can spot whales on boat trips, and maybe even from the shore.
Suggested route & duration
Suggested route 9 nights from Boston
• Boston: 2 nights
• Falmouth: 3 nights
• Stockbridge: 2 nights
• Gloucester: 2 nights
About this independent tour
Why you’ll love this self-drive
• Catch a cruise from coastal towns on Cape Cod and Gloucester for the chance to spot whales
• Stroll around the leafy parks and red-brick streets of charming Boston
• Unwind on Falmouth’s white-sand beaches and catch the ferry over to Martha’s Vineyard
• Pop into shops and cafés along the historic main street of Stockbridge
• This itinerary can also be done in a motorhome.
Suggested self-drive details
Day 1: Boston Soak up the city’s heritage and sights on the famous Freedom Trail. Stay 2 nights at DoubleTree by Hilton Boston - Downtown.
Day 3: Falmouth Relax in one of Cape Cod’s best seaside towns. Stay 3 nights at Inn on the Square.
Day 6: Stockbridge See picturesque backdrops in this small town in the Berkshires. Stay 2 nights at The Red Lion Inn.
Day 8: Gloucester See lighthouses and discover fascinating fishing history in this coastal town on Cape Ann. Stay 2 nights at Ocean House Hotel at Bass Rocks.
Enjoy a day-hike across a section of this scenic hilly route in the Berkshires
Join in the celebrations of the 400-year anniversary of the ship’s arrival into Plymouth
Hop on a ferry from Falmouth to explore this exclusive island for the day
New Bedford Whaling Museum
Learn about the history of whaling, 45 minutes’ drive from Falmouth
Tailor your tour
Make it your own
We’ve crafted this self-drive based on our own experiences and customers’ feedback. It’s fully flexible, so talk to us and we can create your perfect trip.
Where to stay
There are plenty of good chain hotels available, but we’ve handpicked a great selection of mostly boutique, independent hotels which give a real flavour of Massachusetts. We love Ocean House Hotel at Bass Rocks – it has a lovely outdoor pool and an immaculate front lawn overlooking the ocean.
Massachusetts is full of lesser-visited gems. Explore Gloucester, a historic fishing port and the setting for The Perfect Storm, or head to MASS MoCA (Massachusetts Museum of Contemporary Art) in North Adams – this converted factory complex has galleries and performing arts spaces.
Falmouth is a great base for seeing more of Massachusetts, so we recommend spending extra time here. Drive to Plymouth or Hyannis, or catch the ferry to the chic islands of Martha’s Vineyard and Nantucket. Extend your stay in the Berkshires to hike some of the famous Appalachian Trail.
The rest of Massachusetts is easily accessible from each stop on this itinerary, so you don’t necessarily need to add more. If you’re a sports fan, visit Springfield for the basketball hall of fame. It’s also easy to take the train, drive or fly to other cities like New York.
Good to know
When to go
• Visit from May to October when whales can be spotted off the coast
• The most popular time to visit Boston, Massachusetts and the Berkshires is during the autumn ‘leaf-peeping’ season
• Summers can get very busy along the whole New England coast but especially in Cape Cod
• We don’t recommend visiting in the winter