38 days in Massachusetts Itinerary

38 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip builder

Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Boston
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Boston
— 13 nights
Fly
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Provincetown
— 7 nights
Drive
3
Sandwich
— 6 nights
Drive
4
Oak Bluffs, Martha's Vineyard
— 4 nights
Ferry
5
Nantucket
— 7 nights
Fly to Billy Bishop Toronto City, Ferry to Toronto

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Boston

— 13 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.
Venture out of the city with trips to Salem (The House of the Seven Gables, Salem Witch Trials Memorial, &more), Independence Park (in Beverly) and Essex River (in Essex). There's lots more to do: explore the world behind art at Museum of Fine Arts, take in nature's colorful creations at Boston Public Garden, appreciate the extensive heritage of Freedom Trail, and walk around Boston Common.

To find photos, ratings, reviews, and other tourist information, go to the Boston driving holiday planner.

Toronto, Canada to Boston is an approximately 4.5-hour combination of ferry and flight. You can also drive; or take a bus. In June, daily temperatures in Boston can reach 28°C, while at night they dip to 18°C. Cap off your sightseeing on the 7th (Wed) early enough to travel to Provincetown.

Things to do in Boston

Museums · Historic Sites · Parks · Shopping

Side Trips

Provincetown

— 7 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.
Venture out of the city with trips to Eastham (Captain Penniman House, Salt Pond Visitor Center, &more), Chatham (Chatham Railroad Museum, Atwood Museum, &more) and Orleans (Addison Art Gallery, Nauset Beach, &more). And it doesn't end there: appreciate the history behind Pilgrim Monument & Provincetown Museum, kick back and relax at Corn Hill Beach, tour the pleasant surroundings at Race Point Beach, and make a trip to Commercial Street.

For traveler tips, more things to do, and tourist information, use the Provincetown travel tool.

Traveling by flight from Boston to Provincetown takes 2 hours. Alternatively, you can ride a ferry; or drive. In July, plan for daily highs up to 30°C, and evening lows to 20°C. Finish your sightseeing early on the 14th (Wed) to allow enough time to drive to Sandwich.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Sandwich

— 6 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Explore the numerous day-trip ideas around Sandwich: New Bedford Whaling Museum (in New Bedford), Nobska Point Lighthouse (in Woods Hole) and Falmouth (Highfield Hall & Gardens & Falmouth Museums on the Green). There's still lots to do: see the interesting displays at Heritage Museums & Gardens, get engrossed in the history at Plimoth Patuxet, explore the engaging exhibits at Cape Cod Children's Museum, and engage your brain at Sandwich Glass Museum.

To find maps, other places to visit, traveler tips, and other tourist information, read Sandwich tour itinerary builder tool.

Getting from Provincetown to Sandwich by car takes about 1.5 hours. Other options: take a bus. In July in Sandwich, expect temperatures between 31°C during the day and 20°C at night. Finish your sightseeing early on the 20th (Tue) to allow enough time to drive to Oak Bluffs.

Things to do in Sandwich

Museums · Outdoors · Parks · Wildlife

Side Trips

Oak Bluffs, Martha's Vineyard

— 4 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Oak Bluffs is known for beaches, outdoors, and parks. Your plan includes some of its best attractions: don't miss a visit to Flying Horses Carousel, take in nature's colorful creations at Mytoi, stop by Chilmark Chocolates, and pause for some serene contemplation at Old Whaling Church.

For maps, other places to visit, traveler tips, and other tourist information, read our Oak Bluffs online route planner.

Getting from Sandwich to Oak Bluffs by car takes about 1.5 hours. Expect a daytime high around 30°C in July, and nighttime lows around 20°C. Finish your sightseeing early on the 24th (Sat) to allow enough time to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Historic Sites · Parks · Outdoors · Wildlife

Side Trips

Nantucket

— 7 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 plan includes some of its best attractions: see the interesting displays at Whaling Museum, take some stellar pictures from First Congregational Church, visit a coastal fixture at Great Point Light, and get engrossed in the history at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To see traveler tips, more things to do, and other tourist information, you can read our Nantucket holiday planner.

You can ride a ferry from Oak Bluffs to Nantucket in 2 hours. July in Nantucket sees daily highs of 28°C and lows of 20°C at night. Finish your sightseeing early on the 31st (Sat) to allow enough time to travel back home.

Things to do in Nantucket

Historic Sites · Outdoors · Parks · Beaches

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.