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

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

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— 2 nights
West Tisbury
— 2 nights
— 2 nights


Boston — 2 nights

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.
On the 18th (Wed), explore the different monuments and memorials at Mount Auburn Cemetery, stroll around Boston Common, then buy something for everyone on your list at Faneuil Hall Marketplace, and finally appreciate the extensive heritage of Freedom Trail. Keep things going the next day: stroll the grounds of Granary Burying Ground, then admire the natural beauty at Boston Public Garden, then admire the masterpieces at Museum of Fine Arts, and finally admire the striking features of Massachusetts State House.

To find where to stay, photos, ratings, and other tourist information, read our Boston trip itinerary builder tool.

Saint Louis to Boston is an approximately 4.5-hour flight. You can also drive; or take a train. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In May, Boston is little chillier than Saint Louis - with highs of 67°F and lows of 50°F. Finish your sightseeing early on the 20th (Fri) so you can travel to West Tisbury.
Historic Sites · Museums · Parks · Shopping
Side Trip

West Tisbury — 2 nights

West Tisbury is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 20th (Fri), take a stroll through Martha's Vineyard Camp meeting Association (MVCMA), make a trip to Flying Horses Carousel, then visit West Chop, and finally admire the natural beauty at Mytoi. Keep things going the next day: admire the natural beauty at Polly Hill Arboretum, then stroll through Long Point Wildlife Refuge, then visit a coastal fixture at Edgartown Lighthouse, and finally explore the striking landscape at Aquinnah Cliffs.

To see ratings, traveler tips, other places to visit, and other tourist information, read our West Tisbury trip itinerary maker tool.

Drive from Boston to West Tisbury in 2.5 hours. Alternatively, you can drive. May in West Tisbury sees daily highs of 65°F and lows of 47°F at night. Finish up your sightseeing early on the 22nd (Sun) so you can travel to Nantucket.
Parks · Neighborhoods · Historic Sites · Nature
Side Trips

Nantucket — 2 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 22nd (Sun): see the interesting displays at Nantucket Lightship Basket Museum, then enjoy the sand and surf at Madaket Beach, and then kick back and relax at Jetties Beach. On the 23rd (Mon), you'll have a packed day of sightseeing: examine the collection at Whaling Museum, visit a coastal fixture at Brant Point Lighthouse, and then visit a coastal fixture at Sankaty Head Lighthouse.

To see ratings, traveler tips, photos, and other tourist information, you can read our Nantucket attractions planner.

Travel from West Tisbury to Nantucket in 3 hours. In May, daily temperatures in Nantucket can reach 62°F, while at night they dip to 49°F. You will leave for home on the 24th (Tue).
Parks · Beaches · Outdoors · Historic Sites

Martha's Vineyard travel guide

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.