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

Created using Klarna Trips Massachusetts tour planner
Make it your trip
— 2 nights
West Tisbury
— 2 nights
— 3 nights


Boston — 2 nights


Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year.
Start off your visit on the 29th (Thu): take an in-depth tour of John F. Kennedy Presidential Museum & Library, get to know the fascinating history of Freedom Trail, and then browse the different shops at Faneuil Hall Marketplace. Get ready for a full day of sightseeing on the next day: admire the masterpieces at Museum of Fine Arts, then stroll around Boston Public Garden, and then stroll around Boston Common.

To see other places to visit, ratings, and more tourist information, go to the Boston driving holiday planner.

Saint Louis to Boston is an approximately 4.5-hour flight. You can also drive; or take a bus. The time zone difference when traveling from Saint Louis to Boston is 1 hour. In June, Boston is little chillier than Saint Louis - with highs of 76°F and lows of 60°F. Wrap up your sightseeing on the 1st (Sat) early enough to drive to West Tisbury.
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West Tisbury — 2 nights

West Tisbury is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 1st (Sat), admire the natural beauty at Polly Hill Arboretum, then admire the natural beauty at Mytoi, then look for all kinds of wild species at Long Point Wildlife Refuge, and finally take in the dramatic natural features at Aquinnah Cliffs. Keep things going the next day: walk around Ocean Park, don't miss a visit to Flying Horses Carousel, then wander the streets of Martha's Vineyard Camp meeting Association (MVCMA), and finally take a stroll through West Chop.

To see maps, traveler tips, reviews, and more tourist information, you can read our West Tisbury day trip planner.

You can drive from Boston to West Tisbury in 2.5 hours. Another option is to drive. In July, daily temperatures in West Tisbury can reach 79°F, while at night they dip to 63°F. Wrap up your sightseeing on the 3rd (Mon) early enough to travel to Nantucket.
Parks · Neighborhoods · Wildlife · Historic Sites
Side Trips
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Nantucket — 3 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: see the interesting displays at Whaling Museum, make a trip to Nantucket Preservation Trust, see what you can catch with a fishing tour, and get engrossed in the history at Nantucket Shipwreck & Lifesaving Museum.

To find reviews, where to stay, traveler tips, and more tourist information, read our Nantucket trip itinerary maker site.

Traveling by journey from West Tisbury to Nantucket takes 3 hours. July in Nantucket sees daily highs of 76°F and lows of 64°F at night. You will have some time to spend on the 6th (Thu) before leaving for home.
Outdoors · Parks · Beaches · Museums
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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.