11 days in Martha's Vineyard, Salem & Boston Itinerary

11 days in Martha's Vineyard, Salem & Boston Itinerary

Created using Inspirock Massachusetts route planner
Make it your trip
Fly
1
Oak Bluffs
— 2 nights
Fly
2
Salem
— 2 nights
Drive
3
Boston
— 6 nights
Fly

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Oak Bluffs — 2 nights

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. On the 18th (Sat), see the interesting displays at Cottage Museum and then take in nature's colorful creations at Mytoi.

To see maps, reviews, where to stay, and other tourist information, go to the Oak Bluffs online trip itinerary planner.

Tampa to Oak Bluffs is an approximately 6-hour flight. You can also do a combination of bus and ferry; or do a combination of train, taxi, and ferry. While traveling from Tampa, expect a bit cooler days and much colder nights in Oak Bluffs, ranging from highs of 73°F to lows of 54°F. Finish your sightseeing early on the 20th (Mon) so you can fly to Salem.
Parks · Beaches · Outdoors · Historic Sites
Side Trips

Salem — 2 nights

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Take a break from the city and head to Long Sands Beach and Crane Beach. Get a sense of the local culture at The House of the Seven Gables and Salem Witch Museum. Explore the numerous day-trip ideas around Salem: Gloucester (Fishermen's Memorial Monument & Beauport, the Sleeper-McCann House) and Wallis Sands State Beach (in Rye). There's more to do: admire the masterpieces at Peabody Essex Museum and stroll through Pickering Wharf.

To see traveler tips, maps, reviews, and more tourist information, you can read our Salem itinerary builder site.

Traveling by flight from Oak Bluffs to Salem takes 2.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, bus, and train. In June, daytime highs in Salem are 76°F, while nighttime lows are 56°F. Cap off your sightseeing on the 22nd (Wed) early enough to go by car to Boston.
Parks · Beaches · Outdoors · Museums
Side Trips

Boston — 6 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.
Relax by the water at Race Point Beach and Long Point. Your cultural itinerary includes sights like Freedom Trail and Heritage Museums & Gardens. Explore Boston's surroundings by going to Provincetown (Pilgrim Monument & Provincetown Museum & Herring Cove Beach), Sandwich Glass Museum (in Sandwich) and Plymouth Rock (in Plymouth). There's still lots to do: see where the action happens at Fenway Park, admire the masterpieces at Museum of Fine Arts, examine the collection at The Breakers, and explore the galleries of Louisa May Alcott's Orchard House.

For maps, photos, and tourist information, go to the Boston trip planning site.

Getting from Salem to Boston by car takes about an hour. Other options: take a train; or take a bus. In June, daytime highs in Boston are 76°F, while nighttime lows are 60°F. Finish your sightseeing early on the 28th (Tue) so you can fly back home.
Parks · Museums · Historic Sites · Outdoors
Side Trips

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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