14 days in Massachusetts Itinerary

14 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour itinerary maker
Make it your trip
Fly
1
Boston
— 1 night
Fly
2
Edgartown
— 2 nights
Bus to Oak Bluffs, Martha's Vineyard, MA, Ferry to Nantucket
3
Nantucket
— 3 nights
Ferry to Harwich Port, Harwich, MA, Taxi to Chatham
4
Chatham
— 3 nights
Drive
5
Provincetown
— 4 nights
Fly

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Boston — 1 night

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.
Start off your visit on the 21st (Thu): admire the masterpieces at Museum of Fine Arts and then stroll around Boston Public Garden. On the 22nd (Fri), you'll have a packed day of sightseeing: get up close to creatures of the deep with a dolphin and whale watching tour and then kick back and relax at Good Harbor Beach.

To find traveler tips, maps, other places to visit, and more tourist information, use the Boston online tour planner.

London, UK to Boston is an approximately 10.5-hour flight. Traveling from London to Boston, you'll gain 5 hours due to the time zone difference. Traveling from London in July, things will get a bit warmer in Boston: highs are around 33°C and lows about 22°C. Cap off your sightseeing on the 22nd (Fri) early enough to catch the flight to Edgartown.
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Outdoors · Parks · Tours · Wildlife
Side Trip

Edgartown — 2 nights

Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 23rd (Sat): visit Martha's Vineyard Camp meeting Association (MVCMA), make a trip to Flying Horses Carousel, then stroll around Ocean Park, and finally take in nature's colorful creations at Mytoi. Keep things going the next day: enjoy the sea views from Edgartown Lighthouse, then kick back and relax at Katama Beach/ South Beach, then admire the natural beauty at Polly Hill Arboretum, and finally don't miss a visit to Aquinnah Cliffs.

For maps, more things to do, photos, and tourist information, go to the Edgartown holiday planner.

Traveling by flight from Boston to Edgartown takes 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In July, plan for daily highs up to 30°C, and evening lows to 20°C. Wrap up your sightseeing on the 24th (Sun) early enough to travel to Nantucket.
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Parks · Historic Sites · Beaches · Nature
Side Trips

Nantucket — 3 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Explore hidden gems such as Great Point Light and Madaket Beach. And it doesn't end there: see what you can catch with a fishing tour, kick back and relax at Surfside Beach, examine the collection at Nantucket Lightship Basket Museum, and stroll through Nobadeer.

To see other places to visit, reviews, traveler tips, and more tourist information, use the Nantucket trip planner.

You can do a combination of bus and ferry from Edgartown to Nantucket in 2.5 hours. In July, plan for daily highs up to 28°C, and evening lows to 20°C. Finish your sightseeing early on the 27th (Wed) so you can travel to Chatham.
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Outdoors · Beaches · Parks · Historic Sites

Chatham — 3 nights

Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Discover out-of-the-way places like Chatham Marconi Maritime Center and Atwood Museum. There's still lots to do: see majestic marine mammals with a dolphin and whale watching tour, enjoy the sand and surf at Crosby Landing Beach, browse for treasures at Harwich Antiques Center, and tour the pleasant surroundings at Nauset Beach.

For maps, ratings, other places to visit, and other tourist information, go to the Chatham trip itinerary maker tool.

Getting from Nantucket to Chatham by combination of ferry and taxi takes about 2.5 hours. Other options: do a combination of ferry and bus. In July, plan for daily highs up to 30°C, and evening lows to 21°C. Finish up your sightseeing early on the 30th (Sat) so you can go by car to Provincetown.
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Outdoors · Beaches · Parks · Tours
Side Trips

Provincetown — 4 nights

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.
Step off the beaten path and head to Cape Cod Provincelands Trail and Head of the Meadow Beach. You'll find plenty of places to visit near Provincetown: Eastham (Fort Hill Rural Historic District & Captain Penniman House) and Skaket Beach (in Orleans). There's still lots to do: get a new perspective on things with Boat Tours & Water Sports, explore the world behind art at Provincetown Town Hall, stroll through Marconi Beach, and appreciate the history behind Pilgrim Monument & Provincetown Museum.

For other places to visit, ratings, where to stay, and more tourist information, read our Provincetown tour planning website.

Traveling by car from Chatham to Provincetown takes an hour. Alternatively, you can take a bus. In July, daytime highs in Provincetown are 30°C, while nighttime lows are 20°C. Finish your sightseeing early on the 3rd (Wed) so you can fly back home.
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Outdoors · Parks · Beaches · Historic Sites
Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Nightlife
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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Martha's Vineyard travel guide

4.3
Beaches · Lighthouses · Landmarks
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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