6 days in Massachusetts Itinerary

6 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

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Fly to Providence, Ferry to Oak Bluffs
Oak Bluffs, Martha's Vineyard
— 1 night
— 2 nights
— 2 nights


Oak Bluffs, Martha's Vineyard

— 1 night
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 16th (Sat): explore the striking landscape at Aquinnah Cliffs, then visit a coastal fixture at Edgartown Lighthouse, then don't miss a visit to Flying Horses Carousel, and finally visit Martha's Vineyard Camp meeting Association (MVCMA).

To find photos, other places to visit, traveler tips, and other tourist information, go to the Oak Bluffs online itinerary planner.

Orlando to Oak Bluffs is an approximately 7.5-hour combination of flight and ferry. You can also do a combination of car and ferry; or do a combination of train, taxi, and ferry. Plan for much colder temperatures traveling from Orlando in November, with highs in Oak Bluffs at 53°F and lows at 37°F. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Chatham.

Things to do in Oak Bluffs

Historic Sites · Neighborhoods · Nature · Parks

Side Trips


— 2 nights
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Start off your visit on the 17th (Sun): tour the pleasant surroundings at Coast Guard Beach, tour the pleasant surroundings at Herring Cove Beach, and then browse the collection at Provincetown Library. On the 18th (Mon), you'll have a packed day of sightseeing: take an in-depth tour of Salt Pond Visitor Center, enjoy the sand and surf at Nauset Beach, and then take in the waterfront at Chatham Pier and Fish Market.

Plan a Chatham trip in moments using our itinerary builder.

You can drive from Oak Bluffs to Chatham in 2.5 hours. In November, daily temperatures in Chatham can reach 52°F, while at night they dip to 39°F. Finish your sightseeing early on the 18th (Mon) so you can drive to Boston.

Things to do in Chatham

Parks · Beaches · Outdoors · Shopping

Side Trips


— 2 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.
Kick off your visit on the 19th (Tue): ponder the world of politics at Old State House, then explore the world behind art at Museum of Fine Arts, and then walk around Boston Public Garden. Get ready for a full day of sightseeing on the next day: get to know the fascinating history of Freedom Trail, then buy something for everyone on your list at Faneuil Hall Marketplace, and then stroll around Boston Common.

To see traveler tips, where to stay, maps, and other tourist information, read Boston sightseeing planner.

Traveling by car from Chatham to Boston takes 2 hours. Alternatively, you can take a bus. In November, daily temperatures in Boston can reach 52°F, while at night they dip to 37°F. Finish up your sightseeing early on the 20th (Wed) so you can travel back home.

Things to do in Boston

Museums · Parks · Historic Sites · Shopping

Massachusetts travel guide

History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.