4 days in Boston & Martha's Vineyard Itinerary

4 days in Boston & Martha's Vineyard Itinerary

Created using Inspirock Massachusetts trip planner

Make it your trip
— 1 night
Vineyard Haven
— 1 night
Drive to General Edward Lawrence Logan International Airport, Fly to Bradley International Airport, Drive to Albany



— 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 12th (Thu): explore the world behind art at Museum of Fine Arts, then get engrossed in the history at Boston Tea Party Ships & Museum, and then meet the residents at New England Aquarium. On the 13th (Fri), you'll have a packed day of sightseeing: buy something for everyone on your list at Faneuil Hall Marketplace, walk around Boston Public Garden, then walk around Boston Common, then take in the architecture and atmosphere at King's Chapel, and finally wander the streets of North End.

To see more things to do, maps, ratings, and more tourist information, go to the Boston road trip planning website.

Albany to Boston is an approximately 3-hour car ride. You can also drive; or take a bus; or take a train. Traveling from Albany in November, Boston is somewhat warmer at night with lows of 37°F. Cap off your sightseeing on the 13th (Fri) early enough to go by car to Vineyard Haven.

Things to do in Boston

Museums · Parks · Zoos & Aquariums · Neighborhoods

Vineyard Haven

— 1 night
Vineyard Haven is a community within the town of Tisbury on Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 14th (Sat): take a tour by water with Boat Tours & Water Sports, tee off at Farm Neck Golf Club, then visit a coastal fixture at Edgartown Lighthouse, and finally admire the landmark architecture of Trinity Park Tabernacle.

Ask Inspirock to suggest an itinerary and make planning a trip to Vineyard Haven fast, fun, and easy.

Travel from Boston to Vineyard Haven in 2.5 hours. Alternatively, you can drive. In November, daytime highs in Vineyard Haven are 53°F, while nighttime lows are 37°F. Cap off your sightseeing on the 14th (Sat) early enough to travel back home.

Things to do in Vineyard Haven

Outdoors · Historic Sites · Golf · Tours

Side Trips

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.