22 days in Massachusetts Itinerary

22 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner

Make it your trip
Fly
1
Boston
— 6 nights
Fly
2
Provincetown
— 4 nights
Drive
3
Hyannis
— 5 nights
Ferry
4
Nantucket
— 3 nights
Ferry
5
Oak Bluffs, Martha's Vineyard
— 3 nights
Unknown

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Boston

— 6 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.
Change things up with a short trip to Dolphin & Whale Watching in Gloucester (about 50 minutes away). There's still lots to do: admire the masterpieces at Museum of Fine Arts, observe the fascinating underwater world at New England Aquarium, stroll around Boston Common, and don't miss a visit to Boston Public Library.

To find traveler tips, more things to do, photos, and other tourist information, read our Boston trip itinerary planner.

Lisbon, Portugal to Boston is an approximately 10.5-hour flight. Traveling from Lisbon to Boston, you'll gain 5 hours due to the time zone difference. Expect little chillier weather when traveling from Lisbon in June: highs in Boston hover around 28°C, while lows dip to 18°C. Finish your sightseeing early on the 13th (Sat) so you can travel to Provincetown.

Things to do in Boston

Museums · Parks · Historic Sites · Nature

Side Trips

Provincetown

— 4 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.
Change things up with these side-trips from Provincetown: Eastham (Salt Pond Visitor Center, Coast Guard Beach, &more). There's still lots to do: pause for some photo ops at Pilgrim Monument & Provincetown Museum, stroll through Herring Cove Beach, enjoy the sand and surf at Long Point, and browse the collection at Provincetown Library.

To find where to stay, ratings, other places to visit, and tourist information, refer to the Provincetown day trip site.

Traveling by flight from Boston to Provincetown takes 2 hours. Alternatively, you can ride a ferry; or drive. June in Provincetown sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 17th (Wed) so you can drive to Hyannis.

Things to do in Provincetown

Outdoors · Beaches · Parks · Museums

Side Trips

Hyannis

— 5 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Venture out of the city with trips to Chatham (Monomoy National Wildlife Refuge, Chatham Lighthouse Beach, &more), Shining Sea Bikeway (in Falmouth) and Myles Standish Monument State Reservation (in Duxbury). There's lots more to do: see the interesting displays at Heritage Museums & Gardens, kick back and relax at Nauset Beach, admire the majestic nature at Nickerson State Park, and hike along Cape Cod Rail Trail.

To find photos, traveler tips, reviews, and other tourist information, refer to the Hyannis online tour planner.

Getting from Provincetown to Hyannis by car takes about 1.5 hours. Other options: take a bus. In June, daily temperatures in Hyannis can reach 26°C, while at night they dip to 17°C. Finish your sightseeing early on the 22nd (Mon) so you can ride a ferry to Nantucket.

Things to do in Hyannis

Parks · Outdoors · Trails · Beaches

Side Trips

Nantucket

— 3 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your plan includes some of its best attractions: see the interesting displays at Whaling Museum, get to know the fascinating history of Milestone Bog, get engrossed in the history at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum, and tee off at Miacomet Golf Club.

To find maps, traveler tips, where to stay, and other tourist information, read Nantucket trip site.

Ride a ferry from Hyannis to Nantucket in 2 hours. Alternatively, you can fly. June in Nantucket sees daily highs of 24°C and lows of 16°C at night. Cap off your sightseeing on the 25th (Thu) early enough to catch the ferry to Oak Bluffs.

Things to do in Nantucket

Outdoors · Historic Sites · Museums · Parks

Oak Bluffs, Martha's Vineyard

— 3 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 26th (Fri): take in nature's colorful creations at Mytoi, stop by Stefanie Wolf Designs, then visit a coastal fixture at Edgartown Lighthouse, then stroll through Katama Beach/ South Beach, and finally explore the striking landscape at Aquinnah Cliffs. On the next day, admire the striking features of Trinity Park Tabernacle, then make a trip to Flying Horses Carousel, then stop by Martha's Vineyard Camp meeting Association (MVCMA), and finally tee off at Farm Neck Golf Club.

To find where to stay, photos, reviews, and tourist information, read our Oak Bluffs day trip planner.

Ride a ferry from Nantucket to Oak Bluffs in 2 hours. Expect a daytime high around 26°C in June, and nighttime lows around 14°C. Cap off your sightseeing on the 28th (Sun) early enough to travel back home.

Things to do in Oak Bluffs

Historic Sites · Parks · Outdoors · Nature

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.