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

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

Created using Inspirock Massachusetts route builder
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. Start off your visit on the 30th (Fri): examine the collection at Cottage Museum and then admire the natural beauty at Mytoi.

To find traveler tips, other places to visit, ratings, and tourist information, read our Oak Bluffs 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. Prepare for little chillier weather when traveling from Tampa in July: high temperatures in Oak Bluffs hover around 79°F and lows are around 63°F. Wrap up your sightseeing on the 1st (Sun) early enough to 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.
You'll visit kid-friendly attractions like The House of the Seven Gables and Beauport, the Sleeper-McCann House. You'll get in some beach time at Long Sands Beach and Crane Beach. Explore the numerous day-trip ideas around Salem: Wallis Sands State Beach (in Rye) and Fishermen's Memorial Monument (in Gloucester). There's lots more to do: admire the masterpieces at Peabody Essex Museum, go for a stroll along the water at Pickering Wharf, and take an in-depth tour of Salem Witch Museum.

To find reviews, traveler tips, ratings, and more tourist information, read Salem trip itinerary planning site.

You can fly from Oak Bluffs to Salem in 2.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, bus, and train. In August, daytime highs in Salem are 80°F, while nighttime lows are 61°F. Finish up your sightseeing early on the 3rd (Tue) so you can 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.
Get a sense of the local culture at Freedom Trail and John F. Kennedy Presidential Museum & Library. Attractions like Museum of Fine Arts and Fenway Park make great kid-friendly stops. Explore Boston's surroundings by going to Provincetown (Race Point Beach, Pilgrim Monument & Provincetown Museum, &more), Sandwich (Sandwich Glass Museum & Heritage Museums & Gardens) and Plymouth Rock (in Plymouth). And it doesn't end there: stop by North End, get to know the fascinating history of Cliff Walk, take an in-depth tour of Louisa May Alcott's Orchard House, and examine the collection at The Breakers.

For other places to visit, traveler tips, where to stay, and other tourist information, go to the Boston trip itinerary app.

Traveling by car from Salem to Boston takes an hour. Alternatively, you can take a train; or take a bus. In August, daily temperatures in Boston can reach 81°F, while at night they dip to 65°F. Wrap up your sightseeing on the 9th (Mon) early enough to 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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