8 days in Martha's Vineyard, Boston & Portland Itinerary

8 days in Martha's Vineyard, Boston & Portland Itinerary

Created using Inspirock United States trip planner

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Oak Bluffs
— 1 night
— 4 nights
— 2 nights


Oak Bluffs

— 1 night
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. On the 18th (Sat), enjoy the sand and surf at Katama Beach/ South Beach, stop by Stefanie Wolf Designs, then tee off at Farm Neck Golf Club, and finally take a stroll through Martha's Vineyard Camp meeting Association (MVCMA). Keep things going the next day: admire the natural beauty at Mytoi, take in the architecture and atmosphere at Old Whaling Church, enjoy the sea views from Edgartown Lighthouse, then don't miss a visit to Flying Horses Carousel, and finally admire the striking features of Trinity Park Tabernacle.

To see traveler tips, reviews, ratings, and tourist information, read our Oak Bluffs online route maker.

Charlotte to Oak Bluffs is an approximately 4-hour flight. You can also do a combination of car and ferry; or do a combination of train, taxi, and ferry. Expect a bit cooler temperatures when traveling from Charlotte in September; daily highs in Oak Bluffs reach 74°F and lows reach 54°F. Wrap up your sightseeing on the 19th (Sun) to allow time to fly to Boston.

Things to do in Oak Bluffs

Historic Sites · Outdoors · Parks · Neighborhoods

Side Trip


— 4 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.
Change things up with these side-trips from Boston: Sandwich (Sandwich Glass Museum & Heritage Museums & Gardens), Plymouth Rock (in Plymouth) and Dolphin & Whale Watching (in Gloucester). There's lots more to do: admire the natural beauty at Boston Public Garden, browse the collection at John F. Kennedy Presidential Museum & Library, take a stroll through North End, and get engrossed in the history at Boston Tea Party Ships & Museum.

To see reviews, maps, other places to visit, and other tourist information, refer to the Boston trip planner.

Traveling by flight from Oak Bluffs to Boston takes 2.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. In September, daytime highs in Boston are 75°F, while nighttime lows are 59°F. Wrap up your sightseeing on the 23rd (Thu) early enough to drive to Portland.

Things to do in Boston

Museums · Outdoors · Wildlife · Tours

Side Trips


— 2 nights

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Start off your visit on the 24th (Fri): visit a coastal fixture at Nubble Lighthouse, then get to know the fascinating history of Marginal Way Walkway, and then explore the striking landscape at Perkins Cove. Get ready for a full day of sightseeing on the 25th (Sat): visit a coastal fixture at Portland Head Light, then indulge your thirst for a good beer at Allagash Brewing Company, and then head outdoors with Outdoor Activities.

Plan my day in Portland using traveler tips and tourist information provided by Inspirock.

Getting from Boston to Portland by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from Boston in September, Portland is little chillier at night with lows of 52°F. Wrap up your sightseeing on the 25th (Sat) early enough to fly back home.

Things to do in Portland

Historic Sites · Parks · Nature · Breweries & Distilleries

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.