6 days in Boston, Martha's Vineyard & Nantucket Itinerary

Created using Inspirock Massachusetts route maker
Make it your trip
Fly
1
Boston
— 2 nights
Drive
2
West Tisbury
— 1 night
Unknown
3
Nantucket
— 1 night
Fly

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Boston — 2 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year.
Kick off your visit on the 14th (Thu): ponder the world of politics at Massachusetts State House, walk around Boston Common, then visit North End, and finally get to know the fascinating history of Freedom Trail. Get ready for a full day of sightseeing on the 15th (Fri): contemplate the long history of Granary Burying Ground, then admire the masterpieces at Museum of Fine Arts, then admire the natural beauty at Boston Public Garden, and finally browse the different shops at Faneuil Hall Marketplace.

To see more things to do, photos, other places to visit, and more tourist information, use the Boston tour itinerary planner.

Pittsburgh to Boston is an approximately 3.5-hour flight. You can also drive; or take a bus. In September, daytime highs in Boston are 75°F, while nighttime lows are 59°F. Finish up your sightseeing early on the 16th (Sat) so you can go by car to West Tisbury.
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Parks · Museums · Historic Sites · Neighborhoods

West Tisbury — 1 night

West Tisbury is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 16th (Sat): take a stroll through West Chop, then enjoy the sea views from Edgartown Lighthouse, and then stroll through Katama Beach/ South Beach. Get ready for a full day of sightseeing on the 17th (Sun): look for gifts at Stefanie Wolf Designs, then make a trip to Flying Horses Carousel, then visit Martha's Vineyard Camp meeting Association (MVCMA), and finally take in nature's colorful creations at Polly Hill Arboretum.

To see traveler tips, maps, photos, and other tourist information, use the West Tisbury travel planner.

Drive from Boston to West Tisbury in 2.5 hours. Alternatively, you can drive. Traveling from Boston in September, West Tisbury is slightly colder at night with lows of 54°F. Finish up your sightseeing early on the 17th (Sun) so you can travel to Nantucket.
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Neighborhoods · Parks · Beaches · Outdoors
Side Trips

Nantucket — 1 night

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. On the 18th (Mon), examine the collection at Whaling Museum, then enjoy the sea views from Brant Point Lighthouse, and then enjoy the sea views from Sankaty Head Lighthouse.

For traveler tips, maps, other places to visit, and other tourist information, you can read our Nantucket trip itinerary website.

Travel from West Tisbury to Nantucket in 3 hours. In September, daytime highs in Nantucket are 71°F, while nighttime lows are 59°F. Wrap up your sightseeing on the 18th (Mon) early enough to fly back home.
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Historic Sites · Museums

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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