34 days in Massachusetts Itinerary

34 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner
Make it your trip
Fly
1
Provincetown
— 6 nights
Drive
2
Hyannis
— 6 nights
Ferry
3
Nantucket
— 6 nights
Ferry
4
Oak Bluffs, Martha's Vineyard
— 5 nights
Fly
5
Boston
— 10 nights

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Provincetown — 6 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). Spend the 13th (Sat) exploring nature at Cape Cod National Seashore. There's much more to do: kick back and relax at Long Point, tour the pleasant surroundings at Race Point Beach, make a trip to Commercial Street, and see majestic marine mammals with a dolphin and whale watching tour.

To find where to stay, more things to do, traveler tips, and tourist information, read Provincetown route planner.

Boston to Provincetown is an approximately 2-hour flight. You can also ride a ferry; or drive. In August, daily temperatures in Provincetown can reach 78°F, while at night they dip to 62°F. Cap off your sightseeing on the 18th (Thu) early enough to go by car to Hyannis.
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Outdoors · Beaches · Parks · Nature
Side Trips
Find places to stay Aug 12 — 18:
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Hyannis — 6 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Explore the numerous day-trip ideas around Hyannis: Orleans (Nauset Beach & Skaket Beach), Brewster (Crosby Landing Beach & Nickerson State Park) and Falmouth (Wood Neck Beach, Old Silver Beach, &more). The adventure continues: enjoy the sand and surf at Craigville Beach, tour the pleasant surroundings at Mayflower Beach, examine the collection at Heritage Museums & Gardens, and get up close to creatures of the deep with Hyannis Whale Watcher Cruises.

For traveler tips, ratings, photos, and tourist information, read our Hyannis tour itinerary app.

Getting from Provincetown to Hyannis by car takes about 1.5 hours. Other options: take a bus. In August in Hyannis, expect temperatures between 79°F during the day and 63°F at night. Wrap up your sightseeing on the 24th (Wed) early enough to ride a ferry to Nantucket.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Aug 18 — 24:
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Nantucket — 6 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 trip includes some of its best attractions: enjoy the sand and surf at Jetties Beach, tee off at Miacomet Golf Club, tour the pleasant surroundings at Surfside Beach, and do a tasting at Cisco Brewers.

To find more things to do, ratings, maps, and other tourist information, go to the Nantucket trip planner.

Traveling by ferry from Hyannis to Nantucket takes 2 hours. Alternatively, you can fly. In August, daily temperatures in Nantucket can reach 76°F, while at night they dip to 63°F. Finish up your sightseeing early on the 30th (Tue) so you can catch the ferry to Oak Bluffs.
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Outdoors · Parks · Beaches · Wildlife
Find places to stay Aug 24 — 30:
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Oak Bluffs, Martha's Vineyard — 5 nights

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Venture out of the city with trips to Lucy Vincent Beach (in Chilmark) and Menemsha Public Beach (in Menemsha). There's still lots to do: tee off at Farm Neck Golf Club, make a trip to Flying Horses Carousel, stroll through Bend in the Road Beach, and enjoy the sand and surf at Norton Point Beach.

To see where to stay, other places to visit, more things to do, and more tourist information, read our Oak Bluffs trip maker tool.

Ride a ferry from Nantucket to Oak Bluffs in 2 hours. In August in Oak Bluffs, expect temperatures between 79°F during the day and 59°F at night. Finish up your sightseeing early on the 4th (Sun) so you can catch the flight to Boston.
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Outdoors · Parks · Beaches · Historic Sites
Side Trips
Find places to stay Aug 30 — Sep 4:
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Boston — 10 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 these side-trips from Boston: Gloucester (Long Beach, Wingaersheek Beach, &more), Crane Beach (in Ipswich) and Salem (Salem Witch Museum, Salem Food Tours, &more). The adventure continues: take a stroll through North End, make a trip to Newbury Street, take in nature's colorful creations at Boston Public Garden, and walk around Boston Common.

For other places to visit, reviews, and more tourist information, go to the Boston trip planning website.

Fly from Oak Bluffs to Boston in 2.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Expect a daytime high around 75°F in September, and nighttime lows around 59°F. Cap off your sightseeing on the 14th (Wed) early enough to travel back home.
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Museums · Parks · Outdoors · Neighborhoods
Side Trips
Find places to stay Sep 4 — 14:
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Massachusetts travel guide

4.3
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.
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