28 days in Massachusetts Itinerary

28 days in Massachusetts Itinerary

Created using Inspirock Massachusetts holiday planner

Make it your trip
Drive
1
Attleboro
— 4 nights
Drive
2
Boston
— 7 nights
Fly
3
Provincetown
— 4 nights
Drive
4
Hyannis
— 4 nights
Ferry
5
Oak Bluffs, Martha's Vineyard
— 3 nights
Ferry
6
Nantucket
— 5 nights
Fly

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Attleboro

— 4 nights
Attleboro is a city in Bristol County, Massachusetts, United States. Your day by day itinerary now includes Capron Park Zoo. Kids will appreciate attractions like Roger Williams Park Zoo and New Bedford Whaling Museum. You'll find plenty of places to visit near Attleboro: Lizzie Borden House (in Fall River), Indian Head Farm (in Berlin) and Colt State Park (in Bristol). And it doesn't end there: get your game on at Davis Farmland, get lost in a book at Seekonk Public Library, get a taste of life in the country at Harvard Alpaca Ranch, and test your problem-solving skills at popular escape rooms.

For where to stay, more things to do, reviews, and other tourist information, go to the Attleboro trip itinerary planning site.

New York City to Attleboro is an approximately 3.5-hour car ride. Prepare for slightly colder weather when traveling from New York City in October: high temperatures in Attleboro hover around 63°F and lows are around 44°F. Wrap up your sightseeing on the 30th (Wed) to allow time to drive to Boston.

Things to do in Attleboro

Parks · Museums · Zoos & Aquariums · Fun & Games

Side Trips

Boston

— 7 nights

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.
Kids will appreciate attractions like Museum of Fine Arts and Freedom Trail. Explore Boston's surroundings by going to Dolphin & Whale Watching (in Gloucester), Salem (Salem Witch Museum, Grace Episcopal Church, &more) and Concord (Minuteman National Park - Old North Bridge, Louisa May Alcott's Orchard House, &more). The adventure continues: admire the natural beauty at Boston Public Garden, wander the streets of North End, browse the collection at John F. Kennedy Presidential Museum & Library, and take a tour by water with Boat Tours & Water Sports.

Take the guesswork out of planning a Boston vacation by using our trip itinerary maker.

Traveling by car from Attleboro to Boston takes an hour. Traveling from Attleboro in October, you can expect nighttime temperatures to be somewhat warmer in Boston, with lows of 50°F. Cap off your sightseeing on the 6th (Wed) early enough to travel to Provincetown.

Things to do in Boston

Museums · Historic Sites · Parks · Tours

Side Trips

Provincetown

— 4 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Family-friendly places like Cape Cod National Seashore and Nauset Beach will thrill your kids. Get out of town with these interesting Provincetown side-trips: Eastham (Nauset Light Beach & Coast Guard Beach). There's lots more to do: kick back and relax at Race Point Beach, learn about winemaking at Truro Vineyards of Cape Cod, tour the pleasant surroundings at Long Point, and make a trip to Commercial Street.

For traveler tips, photos, maps, and other tourist information, read Provincetown vacation maker.

You can fly from Boston to Provincetown in 2 hours. Other options are to ride a ferry; or drive. Expect a daytime high around 51°F in November, and nighttime lows around 39°F. Finish up your sightseeing early on the 10th (Sun) so you can go by car to Hyannis.

Things to do in Provincetown

Parks · Beaches · Outdoors · Museums

Side Trips

Hyannis

— 4 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Bring the kids along to Sandwich Glass Museum and Old King's Hwy. Change things up with these side-trips from Hyannis: Plymouth (Mayflower II, Plymouth Rock, &more), Falmouth (Shining Sea Bikeway & Old Silver Beach) and Woods Hole (Woods Hole Science Aquarium & Nobska Point Lighthouse). And it doesn't end there: look for all kinds of wild species at Monomoy National Wildlife Refuge, see the interesting displays at Heritage Museums & Gardens, deepen your understanding at Cape Cod Children's Museum, and steep yourself in history at Hoxie House.

Plan my trip to Hyannis with suggested itineraries provided by Inspirock.

Traveling by car from Provincetown to Hyannis takes 1.5 hours. Alternatively, you can take a bus. In November, daytime highs in Hyannis are 53°F, while nighttime lows are 37°F. Finish your sightseeing early on the 14th (Thu) to allow enough time to ride a ferry to Oak Bluffs.

Things to do in Hyannis

Museums · Parks · Outdoors · Wildlife

Side Trips

Oak Bluffs, Martha's Vineyard

— 3 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Family-friendly places like Trinity Park Tabernacle and Edgartown Lighthouse will thrill your kids. Step out of Oak Bluffs to go to Menemsha and see Menemsha Public Beach, which is approximately 32 minutes away. There's still lots to do: tee off at Farm Neck Golf Club, take a stroll through Martha's Vineyard Camp meeting Association (MVCMA), don't miss a visit to Edgartown Books, and stop by Stefanie Wolf Designs.

To find reviews, where to stay, more things to do, and other tourist information, read Oak Bluffs trip tool.

Traveling by ferry from Hyannis to Oak Bluffs takes 1.5 hours. Alternatively, you can do a combination of taxi and ferry; or do a combination of bus and ferry. In November, daily temperatures in Oak Bluffs can reach 53°F, while at night they dip to 37°F. Wrap up your sightseeing on the 17th (Sun) early enough to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Parks · Outdoors · Neighborhoods · Beaches

Side Trips

Nantucket

— 5 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kids will enjoy Whaling Museum and Great Point Light. There's still lots to do: play a few rounds at Miacomet Golf Club, see the interesting displays at Nantucket Lightship Basket Museum, steep yourself in history at Oldest House (Jethro Coffin House) and Kitchen Garden, and enjoy the sea views from Brant Point Lighthouse.

For maps, other places to visit, where to stay, and more tourist information, read our Nantucket trip planning website.

Traveling by ferry from Oak Bluffs to Nantucket takes 2 hours. In November in Nantucket, expect temperatures between 53°F during the day and 41°F at night. Cap off your sightseeing on the 22nd (Fri) early enough to travel back home.

Things to do in Nantucket

Historic Sites · Parks · Outdoors · Museums

Massachusetts travel guide

4.3
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.