44 days in Massachusetts Itinerary

44 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner
Make it your trip
Drive
1
Agawam
— 1 night
Drive
2
Boston
— 9 nights
Fly
3
Nantucket
— 8 nights
Ferry
4
Oak Bluffs, Martha's Vineyard
— 8 nights
Ferry
5
Hyannis
— 8 nights
Drive
6
Provincetown
— 9 nights
Fly

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Agawam — 1 night

Agawam is a city in Hampden County, Massachusetts, United States. Six Flags New England has been added to your itinerary. Kick off your visit on the 20th (Mon): stroll through Redstone Rail Trail and then stroll around Heritage Park. Get ready for a full day of sightseeing on the 21st (Tue): admire the majestic nature at Robinson State Park, find something for the whole family at Six Flags New England, and then play a few rounds at Crestview Country Club.

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

Boston to Agawam is an approximately 2-hour car ride. In April, plan for daily highs up to 59°F, and evening lows to 36°F. Cap off your sightseeing on the 21st (Tue) early enough to go by car to Boston.
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Parks · Outdoors · Trails · Golf
Side Trip

Boston — 9 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.
Get out of town with these interesting Boston side-trips: Concord (Walden Pond State Reservation & Louisa May Alcott's Orchard House) and Salem (Grace Episcopal Church, Peabody Essex Museum, &more). There's still lots to do: explore the world behind art at Museum of Fine Arts, get lost in a book at John F. Kennedy Presidential Museum & Library, buy something for everyone on your list at Faneuil Hall Marketplace, and wander the streets of North End.

To find more things to do, photos, where to stay, and other tourist information, read our Boston trip builder site.

Traveling by car from Agawam to Boston takes 2 hours. In April, daily temperatures in Boston can reach 56°F, while at night they dip to 40°F. Finish your sightseeing early on the 30th (Thu) to allow enough time to fly to Nantucket.
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Museums · Parks · Historic Sites · Tours
Side Trips

Nantucket — 8 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your trip includes some of its best attractions: examine the collection at Whaling Museum, engage your brain at Maria Mitchell Association, make a trip to Nantucket Founders Burial Ground, and identify plant and animal life at Coskata-Coatue Wildlife Refuge.

For maps, other places to visit, reviews, and tourist information, go to the Nantucket trip itinerary planner.

Getting from Boston to Nantucket by flight takes about 2.5 hours. Other options: do a combination of car and ferry; or do a combination of bus and ferry. In April in Nantucket, expect temperatures between 52°F during the day and 39°F at night. Wrap up your sightseeing on the 8th (Fri) to allow time to ride a ferry to Oak Bluffs.
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Historic Sites · Parks · Outdoors · Beaches

Oak Bluffs, Martha's Vineyard — 8 nights

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Get out of town with these interesting Oak Bluffs side-trips: Gay Head Lighthouse (in Aquinnah) and Menemsha Public Beach (in Menemsha). Next up on the itinerary: enjoy the sea views from Edgartown Lighthouse, look for all kinds of wild species at Cedar Tree Neck Sanctuary, pause for some serene contemplation at St. Elizabeth Catholic Church, and admire the landmark architecture of Trinity Park Tabernacle.

To see ratings, traveler tips, more things to do, and more tourist information, read our Oak Bluffs trip planner.

You can ride a ferry from Nantucket to Oak Bluffs in 2 hours. In May, daytime highs in Oak Bluffs are 65°F, while nighttime lows are 47°F. Finish your sightseeing early on the 16th (Sat) so you can ride a ferry to Hyannis.
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Parks · Outdoors · Wildlife · Beaches
Side Trips

Hyannis — 8 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Explore Hyannis' surroundings by going to Falmouth (Old Silver Beach, Spohr Gardens, &more), Cape Cod Canal (in Buzzards Bay) and Plymouth (Plimoth Patuxet Museums, Plymouth Rock, &more). The adventure continues: take an in-depth tour of Sandwich Glass Museum, tee off at Cranberry Valley Golf Course, have fun and explore at Cape Cod Children's Museum, and don't miss a visit to Old King's Hwy.

To see more things to do, ratings, reviews, and other tourist information, refer to the Hyannis travel tool.

Traveling by ferry from Oak Bluffs to Hyannis takes 1.5 hours. Alternatively, you can do a combination of ferry and taxi; or do a combination of ferry and bus. In May, daily temperatures in Hyannis can reach 65°F, while at night they dip to 49°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Provincetown.
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Parks · Outdoors · Museums · Beaches
Side Trips

Provincetown — 9 nights

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.
Explore the numerous day-trip ideas around Provincetown: Eastham (Captain Penniman House, Salt Pond Visitor Center, &more). Next up on the itinerary: explore the wealth of natural beauty at Cape Cod National Seashore, enjoy the sand and surf at Marconi Beach, browse the collection at Provincetown Library, and hike along Cape Cod Provincelands Trail.

For photos, maps, where to stay, and tourist information, you can read our Provincetown road trip planning site.

You can drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. In May, daytime highs in Provincetown are 63°F, while nighttime lows are 48°F. Wrap up your sightseeing by early afternoon on the 2nd (Tue) to allow enough time to fly back home.
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Parks · Outdoors · Beaches · Nature
Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Nightlife
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.
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