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

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

Created using Inspirock Massachusetts trip itinerary builder

Plan created by another user. Make it yours
1
Oak Bluffs
— 2 nights
2
Salem
— 2 nights
3
Boston
— 6 nights

S M T W T F S
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17

2
nights
Oak Bluffs

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 4th (Sun): examine the collection at Cottage Museum and then admire the natural beauty at Mytoi.

To see ratings, other places to visit, more things to do, and other tourist information, refer to the Oak Bluffs day trip planning app.

Tampa to Oak Bluffs is an approximately 8-hour flight. You can also do a combination of bus and ferry; or do a combination of train, taxi, and ferry. Plan for cooler temperatures traveling from Tampa in October, with highs in Oak Bluffs at 65°F and lows at 46°F. Cap off your sightseeing on the 6th (Tue) early enough to travel to Salem.

Things to do in Oak Bluffs

Parks · Beaches · Outdoors · Historic Sites

Side Trips

Highlights from your plan
Lambert's Cove Beach ©
Lambert's Cove Beach
Edgartown Lighthouse ©
Edgartown Lighthouse
Trinity Park Tabernacle ©
Trinity Park Tabernacle

2
nights
Salem

Salem ©

Witch City

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 explore and learn at The House of the Seven Gables and Peabody Essex Museum. Escape the urban bustle at Long Sands Beach and Crane Beach. Get out of town with these interesting Salem side-trips: Gloucester (Fishermen's Memorial Monument & Beauport, the Sleeper-McCann House) and Wallis Sands State Beach (in Rye). It doesn't end there: take an in-depth tour of Salem Witch Museum and take in the waterfront activity at Pickering Wharf.

For maps, ratings, reviews, and tourist information, you can read our Salem sightseeing planner.

Do a combination of ferry and car from Oak Bluffs to Salem in 3.5 hours. Alternatively, you can fly; or do a combination of ferry and bus. In October, plan for daily highs up to 64°F, and evening lows to 45°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to drive to Boston.

Things to do in Salem

Parks · Beaches · Outdoors · Museums

Side Trips

Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Peabody Essex Museum ©
Peabody Essex Museum
Salem Witch Museum ©
Salem Witch Museum

6
nights
Boston

Boston ©

Beantown

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 John F. Kennedy Presidential Museum & Library and Louisa May Alcott's Orchard House. Visit Race Point Beach and Herring Cove Beach for some beach relaxation. Explore the numerous day-trip ideas around Boston: Plymouth Rock (in Plymouth), Sandwich (Sandwich Glass Museum & Heritage Museums & Gardens) and Provincetown (Pilgrim Monument & Provincetown Museum & Long Point). There's lots more to do: get to know the fascinating history of Freedom Trail, wander the streets of North End, hike along Cliff Walk, and see where the action happens at Fenway Park.

To see where to stay, photos, traveler tips, and more tourist information, go to the Boston trip builder tool.

Traveling by car from Salem to Boston takes an hour. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Boston can reach 64°F, while at night they dip to 50°F. Finish your sightseeing early on the 14th (Wed) so you can travel back home.

Things to do in Boston

Side Trips

Highlights from your plan
John F. Kennedy Presidential Museum & Library ©
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

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