7 days in Massachusetts Itinerary
Created using Klarna Trips Massachusetts trip planner
Start: Boston
Drive
1
Plymouth
— 1 night
Drive
2
Hyannis
— 1 night
Drive
3
Provincetown
— 2 nights
Taxi to Hyannis, MA, Ferry to Oak Bluffs
4
Oak Bluffs
— 2 nights
Ferry
5
Nantucket
— 1 day
Fly
End: New York City
Wed, Jun 14 - Tue, Jun 20
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Plymouth — 1 night
America's Hometown
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.Start off your visit on the 14th (Wed): take an in-depth tour of Pilgrim Hall Museum, then take an in-depth tour of Plimoth Patuxet Museums, and then view the masterpieces at Richard Sparrow House. Here are some ideas for day two: pause for some photo ops at Plymouth Rock, steep yourself in history at Mayflower II, examine the collection at The Jenney, then walk around Ellisville Harbor State Park, and finally see the interesting displays at Heritage Museums & Gardens.
To find traveler tips, more things to do, reviews, and other tourist information, use the Plymouth travel route planner.
Boston to Plymouth is an approximately 1-hour car ride. You can also take a train; or take a bus. June in Plymouth sees daily highs of 28°C and lows of 15°C at night. Finish up your sightseeing early on the 15th (Thu) so you can go by car to Hyannis.
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Hyannis — 1 night

Capital of Cape Cod
"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.Kick off your visit on the 15th (Thu): make a trip to Gallery Artrio.
To see other places to visit, maps, photos, and more tourist information, read our Hyannis route planner.
Getting from Plymouth to Hyannis by car takes about an hour. Other options: take a bus. In June, plan for daily highs up to 26°C, and evening lows to 17°C. Finish your sightseeing early on the 16th (Fri) to allow enough time to drive to Provincetown.
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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.On the 17th (Sat), get a new perspective on things with Dolphin Fleet Whale Watch, then take a leisurely stroll along MacMillan Wharf, then don't miss a visit to Commercial Street, and finally pause for some photo ops at Pilgrim Monument & Provincetown Museum. Here are some ideas for day two: kick back and relax at Race Point Beach and then kick back and relax at Herring Cove Beach.
To see more things to do, traveler tips, photos, and more tourist information, you can read our Provincetown trip itinerary maker website.
Traveling by car from Hyannis to Provincetown takes 1.5 hours. Alternatively, you can drive; or take a bus. June in Provincetown sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 18th (Sun) to allow enough time to travel to Oak Bluffs.
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Oak Bluffs — 2 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 19th (Mon): take in the dramatic natural features at Aquinnah Cliffs, then enjoy the sand and surf at Katama Beach/ South Beach, then make a trip to Flying Horses Carousel, and finally stop by Martha's Vineyard Camp meeting Association (MVCMA).
To find where to stay, more things to do, ratings, and other tourist information, refer to the Oak Bluffs trip planning tool.
Getting from Provincetown to Oak Bluffs by combination of taxi and ferry takes about 3 hours. Other options: do a combination of car and ferry; or do a combination of bus and ferry. Expect a daytime high around 26°C in June, and nighttime lows around 14°C. Finish your sightseeing early on the 20th (Tue) so you can ride a ferry to Nantucket.
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To find where to stay, more things to do, ratings, and other tourist information, refer to the Oak Bluffs trip planning tool.
Getting from Provincetown to Oak Bluffs by combination of taxi and ferry takes about 3 hours. Other options: do a combination of car and ferry; or do a combination of bus and ferry. Expect a daytime high around 26°C in June, and nighttime lows around 14°C. Finish your sightseeing early on the 20th (Tue) so you can ride a ferry to Nantucket.
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Nantucket — 1 day
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. On the 20th (Tue), tour the pleasant surroundings at Madaket Beach, then kick back and relax at Jetties Beach, and then examine the collection at Whaling Museum.
For where to stay, more things to do, and more tourist information, you can read our Nantucket trip itinerary tool.
Getting from Oak Bluffs to Nantucket by ferry takes about 2 hours. In June, plan for daily highs up to 24°C, and evening lows to 16°C. Finish up your sightseeing early on the 20th (Tue) so you can catch the flight back home.
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For where to stay, more things to do, and more tourist information, you can read our Nantucket trip itinerary tool.
Getting from Oak Bluffs to Nantucket by ferry takes about 2 hours. In June, plan for daily highs up to 24°C, and evening lows to 16°C. Finish up your sightseeing early on the 20th (Tue) so you can catch the flight back home.
Find places to stay Jun 20 — 21:
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Massachusetts travel guide
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.
Cape Cod travel guide
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.
Martha's Vineyard travel guide
Martha's Vineyard is an island located south of Cape Cod in Massachusetts that is known for being an affluent summer colony. It includes the smaller Chappaquiddick Island which is usually connected to the Vineyard, though storms and hurricanes have been known to separate the two. The last such separation of the islands was in 2007 and the two islands are again connected as of April 2, 2015.It is the 58th largest island in the United States, with a land area of 100sqmi, and the third largest on the East Coast of the United States, after Long Island and Mount Desert Island. The island constitutes the bulk of Dukes County, Massachusetts, which also includes the Elizabeth Islands and the island of Nomans Land.The Vineyard was home to one of the earliest known deaf communities in the United States; consequently, a special sign language developed on the island called Martha's Vineyard Sign Language (MVSL).The 2010 census reported a year-round population of 16,535 residents, although the summer population can swell to more than 100,000 people. About 56% of the Vineyard's 14,621 homes are seasonally occupied.
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