8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner

Make it your trip
Fly
1
Boston
— 3 nights
Fly
2
Provincetown
— 2 nights
Drive
3
Sandwich
— 2 nights
Drive

S M T W T F S
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10
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16
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19

Boston

— 3 nights

Beantown

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.
When in Boston, make a side trip to see Dolphin & Whale Watching in Gloucester, approximately Gloucester away. Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, take an in-depth tour of USS Constitution Museum, get lost in a book at John F. Kennedy Presidential Museum & Library, and traverse land and water with a duck tour.

To see photos, other places to visit, ratings, and more tourist information, refer to the Boston trip planning app.

New York City to Boston is an approximately 3.5-hour flight. You can also drive; or take a train. Traveling from New York City in October, things will get a bit cooler in Boston: highs are around 64°F and lows about 50°F. Wrap up your sightseeing on the 14th (Mon) early enough to travel to Provincetown.

Things to do in Boston

Museums · Parks · Tours · Wildlife

Side Trip

Provincetown

— 2 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.
Start off your visit on the 15th (Tue): take a leisurely stroll along MacMillan Wharf, then ponder the world of politics at Provincetown Town Hall, and then enjoy the sand and surf at Cape Cod National Seashore. Here are some ideas for day two: browse the collection at Provincetown Library, then enjoy the sand and surf at Herring Cove Beach, then pause for some photo ops at Pilgrim Monument & Provincetown Museum, and finally tour the pleasant surroundings at Race Point Beach.

For where to stay, maps, reviews, and other tourist information, you can read our Provincetown trip itinerary site.

Getting from Boston to Provincetown by flight takes about 2 hours. Other options: ride a ferry; or drive. In October in Provincetown, expect temperatures between 63°F during the day and 49°F at night. Finish your sightseeing early on the 16th (Wed) so you can drive to Sandwich.

Things to do in Provincetown

Parks · Beaches · Outdoors · Museums

Side Trip

Sandwich

— 2 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Kick off your visit on the 17th (Thu): contemplate the long history of Mayflower II, appreciate the history behind Plymouth Rock, get engrossed in the history at Plimoth Patuxet, then admire the masterpieces at Sandwich Glass Museum, and finally admire the majestic nature at National Monument to the Forefathers. Get ready for a full day of sightseeing on the next day: examine the collection at Heritage Museums & Gardens, then explore the landscape on two wheels at Shining Sea Bikeway, and then tour the pleasant surroundings at Chatham Lighthouse Beach.

For photos and more tourist information, go to the Sandwich online tour itinerary builder.

Drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. In October in Sandwich, expect temperatures between 64°F during the day and 46°F at night. Finish your sightseeing early on the 18th (Fri) so you can drive back home.

Things to do in Sandwich

Museums · Parks · Outdoors · Trails

Side Trips

Massachusetts travel guide

4.3
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.