4 days in Massachusetts Itinerary

4 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip maker

Make it your trip
— 1 night
West Tisbury, Martha's Vineyard
— 1 night
— 1 night
Drive to General Edward Lawrence Logan International Airport, Fly to Los Angeles



— 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.
On the 25th (Sun), explore the world behind art at Museum of Fine Arts and then walk around Rose Kennedy Greenway. Get ready for a full day of sightseeing on the next day: browse the different shops at Faneuil Hall Marketplace, then meet the residents at New England Aquarium, then walk around Boston Public Garden, and finally traverse land and water with a duck tour.

To see other places to visit, maps, more things to do, and tourist information, read our Boston trip planner.

Los Angeles to Boston is an approximately 7-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll lose 3 hours traveling from Los Angeles to Boston. July in Boston sees daily highs of 83°F and lows of 67°F at night. Wrap up your sightseeing on the 26th (Mon) early enough to travel to West Tisbury.

Things to do in Boston

Parks · Museums · Zoos & Aquariums · Tours

West Tisbury, Martha's Vineyard

— 1 night
West Tisbury is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 27th (Tue): play a few rounds at Farm Neck Golf Club, contemplate the long history of Trinity Park Tabernacle, then don't miss a visit to Flying Horses Carousel, and finally enjoy the sand and surf at Joseph Sylvia State Beach.

For reviews, where to stay, ratings, and more tourist information, you can read our West Tisbury tour itinerary 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. Finish your sightseeing early on the 27th (Tue) so you can travel to Foxborough.

Things to do in West Tisbury

Outdoors · Beaches · Parks · Golf

Side Trip


— 1 night
Foxborough is a town in Norfolk County, Massachusetts, United States, about 22mi southwest of Boston and 18mi northeast of Providence, Rhode Island. Gillette Stadium has been added to your itinerary. Start off your visit on the 28th (Wed): trek along The Nature Trail And Cranberry Bog and then enjoy some diversion at Gillette Stadium.

For where to stay, traveler tips, other places to visit, and more tourist information, read our Foxborough driving holiday tool.

Traveling by car from West Tisbury to Foxborough takes 2.5 hours. Alternatively, you can drive. July in Foxborough sees daily highs of 84°F and lows of 62°F at night. Cap off your sightseeing on the 28th (Wed) early enough to travel back home.

Things to do in Foxborough

Trails · Parks · Outdoors · Fun & Games

Massachusetts travel guide

History Museums · Art Museums · Historic Walking Areas
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.

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.