6 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner
Make it your trip
— 2 nights
— 1 night
— 1 night
Oak Bluffs
— 1 night


Boston — 2 nights


Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year.
Take a break from Boston with a short trip to Dolphin & Whale Watching in Gloucester, about 50 minutes away. There's lots more to do: admire the natural beauty at Boston Public Garden, take a tour of Boston Tea Party Ships & Museum, stroll around Boston Common, and admire the masterpieces at Museum of Fine Arts.

To find reviews, where to stay, maps, and other tourist information, read Boston holiday planning website.

Kansas City to Boston is an approximately 5-hour flight. You can also drive; or do a combination of tram and train. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. September in Boston sees daily highs of 75°F and lows of 59°F at night. Cap off your sightseeing on the 12th (Tue) early enough to go by car to Hyannis.
Museums · Tours · Outdoors · Wildlife
Side Trip

Hyannis — 1 night

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
On the 13th (Wed), contemplate the long history of Hoxie House, see the interesting displays at Heritage Museums & Gardens, then engage your brain at Sandwich Glass Museum, and finally don't miss a visit to Old King's Hwy.

To see maps, traveler tips, other places to visit, and other tourist information, refer to the Hyannis day trip app.

You can drive from Boston to Hyannis in 1.5 hours. Alternatively, you can take a bus; or fly. September in Hyannis sees daily highs of 73°F and lows of 57°F at night. Finish your sightseeing early on the 13th (Wed) so you can ride a ferry to Nantucket.
Museums · Childrens Museums · Historic Sites
Side Trip

Nantucket — 1 night

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 14th (Thu): examine the collection at Whaling Museum, then visit a coastal fixture at Great Point Light, and then enjoy the sea views from Sankaty Head Lighthouse.

To see traveler tips, where to stay, more things to do, and tourist information, read our Nantucket trip planner.

Traveling by ferry from Hyannis to Nantucket takes 2 hours. Alternatively, you can fly. September in Nantucket sees daily highs of 71°F and lows of 59°F at night. Finish your sightseeing early on the 14th (Thu) to allow enough time to ride a ferry to Oak Bluffs.
Historic Sites · Museums

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 15th (Fri), look for all kinds of wild species at Sheriff's Meadow Sanctuary, take in the architecture and atmosphere at Old Whaling Church, and then admire the landmark architecture of Trinity Park Tabernacle.

To see ratings, maps, and tourist information, refer to the Oak Bluffs trip planner.

Getting from Nantucket to Oak Bluffs by ferry takes about 2 hours. Traveling from Nantucket in September, plan for slightly colder nights in Oak Bluffs, with lows around 54°F. Finish your sightseeing early on the 15th (Fri) so you can fly back home.
Historic Sites · Parks · Wildlife
Side Trip
Highlights from your trip

Massachusetts travel guide

History Museums · Nightlife · Art Museums
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.

Cape Cod travel guide

Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.

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.