8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

Created using Inspirock Massachusetts planner

Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Provincetown
— 3 nights
— 3 nights
— 1 night
Drive to Bradley International Airport, Fly to Lester B. Pearson International Airport



— 3 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Take a break from the city and head to Cape Cod National Seashore and Race Point Beach. Attractions like Nauset Beach and Pilgrim Monument & Provincetown Museum make great kid-friendly stops. Explore Provincetown's surroundings by going to Cape Cod Canal (in Buzzards Bay) and Coast Guard Beach (in Eastham). Next up on the itinerary: tour the pleasant surroundings at Herring Cove Beach, take in the waterfront at MacMillan Wharf, get lost in a book at Provincetown Library, and enjoy the sand and surf at Marconi Beach.

Discover how to plan a Provincetown trip in just a few steps with Inspirock's itinerary builder.

Toronto, Canada to Provincetown is an approximately 6.5-hour combination of ferry and flight. You can also drive; or take a bus. In August in Provincetown, expect temperatures between 30°C during the day and 19°C at night. Wrap up your sightseeing on the 7th (Wed) early enough to travel to Boston.

Things to do in Provincetown

Parks · Beaches · Outdoors · Museums

Side Trips


— 3 nights


Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Kids will enjoy Boston Public Garden and New England Aquarium. Go for a jaunt from Boston to Gloucester to see Dolphin & Whale Watching about 50 minutes away. And it doesn't end there: explore the world behind art at Museum of Fine Arts, get a taste of the local shopping with Faneuil Hall Marketplace, stroll around Rose Kennedy Greenway, and engage your brain at Museum of Science.

To see traveler tips, photos, where to stay, and more tourist information, you can read our Boston travel itinerary planner.

You can fly from Provincetown to Boston in 2 hours. Other options are to ride a ferry; or drive. In August, daily temperatures in Boston can reach 32°C, while at night they dip to 21°C. Finish your sightseeing early on the 10th (Sat) to allow enough time to travel to Hancock.

Things to do in Boston

Museums · Tours · Wildlife · Parks

Side Trip


— 1 night
Hancock is a town in Berkshire County, Massachusetts, United States. On the 11th (Sun), experience rural life at Ioka Valley Farm and then take your sightseeing to a higher altitude at Mount Greylock.

For ratings, reviews, photos, and tourist information, read our Hancock online trip maker.

Traveling by car from Boston to Hancock takes 3 hours. Traveling from Boston in August, expect a bit cooler with lows of 15°C in Hancock. Wrap up your sightseeing on the 11th (Sun) early enough to travel back home.

Things to do in Hancock

Nature · Parks

Side Trip

Massachusetts travel guide

History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.