29 days in Massachusetts Itinerary

29 days in Massachusetts Itinerary

Created using Inspirock Massachusetts sightseeing planner

Plan created by another user. Make it yours

Route & dates

1
Boston
— 7 nights
2
Nantucket
— 5 nights
3
Provincetown
— 6 nights
4
Falmouth
— 6 nights
5
Westfield
— 4 nights

7
nights
Boston

Boston ©
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 (Peabody Essex Museum, Salem Witch Museum, &more) and Dolphin & Whale Watching (in Gloucester). There's lots more to do: admire the natural beauty at Boston Public Garden, take an in-depth tour of Boston Tea Party Ships & Museum, appreciate the extensive heritage of Freedom Trail, and admire nature's wide array of creatures at New England Aquarium.

To find maps, more things to do, reviews, and tourist information, read our Boston trip planner.

Washington DC to Boston is an approximately 3.5-hour flight. You can also take a train; or drive. Plan for a bit cooler temperatures traveling from Washington DC in April, with highs in Boston at °F and lows at °F. Wrap up your sightseeing on the 2nd (Sat) to allow time to travel to Nantucket.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Cambridge, The Plumbing Museum, sophia's greek pantry, Cutler Park
Highlights from your plan
Boston Public Garden ©
Boston Public Garden
Boston Common ©
Boston Common
Museum of Science ©
Museum of Science

5
nights
Nantucket

Nantucket ©
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, make a trip to Nantucket Founders Burial Ground, play a few rounds at Miacomet Golf Club, and get to know the fascinating history of Milestone Bog.

To find reviews, more things to do, other places to visit, and other tourist information, you can read our Nantucket online route builder.

Traveling by combination of from Boston to Nantucket takes 3 hours. Alternatively, you can do a combination of car and ferry; or take a bus. When traveling from Boston in May, plan for slightly colder days and about the same nights in Nantucket: temperatures range from °F by day to °F at night. Finish your sightseeing early on the 7th (Thu) to allow enough time to travel to Provincetown.

Things to do in Nantucket

Historic Sites Museums Childrens Museums
Highlights from your plan
Whaling Museum ©
Whaling Museum
Miacomet Golf Club ©
Miacomet Golf Club

6
nights
Provincetown

Provincetown ©
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 Provincetown's surroundings by going to Chatham (Atwood Museum & Chatham Railroad Museum) and Eastham (Salt Pond Visitor Center, Captain Penniman House, &more). Next up on the itinerary: stroll through Cape Cod National Seashore, browse the collection at Provincetown Library, enjoy the sand and surf at Herring Cove Beach, and see majestic marine mammals with a dolphin and whale watching tour.

To see more things to do, reviews, other places to visit, and other tourist information, go to the Provincetown journey maker.

Do a combination of ferry and taxi from Nantucket to Provincetown in 3 hours. Alternatively, you can fly; or do a combination of ferry and bus. May in Provincetown sees daily highs of °F and lows of °F at night. Wrap up your sightseeing on the 13th (Wed) early enough to drive to Falmouth.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Wellfleet, Eastham, Chatham, Truro Vineyards of Cape Cod, Cape Cod National Seashore
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©
Pilgrim Monument & Provincetown Museum
Race Point Beach ©
Race Point Beach

6
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Explore Falmouth's surroundings by going to Sandwich (Heritage Museums & Gardens & Old King's Hwy), The Cape Cod Canal Bikeway (in Bourne) and Cape Cod Canal (in Buzzards Bay). The adventure continues: engage your brain at Sandwich Glass Museum, grab your bike and head to Shining Sea Bikeway, visit a coastal fixture at Edgartown Lighthouse, and don't miss a visit to Mayflower II.

Find out how to plan Falmouth trip without stress by asking Inspirock to help create an itinerary.

You can drive from Provincetown to Falmouth in 2 hours. Another option is to take a bus. May in Falmouth sees daily highs of °F and lows of °F at night. Finish up your sightseeing early on the 19th (Tue) so you can travel to Westfield.

Things to do in Falmouth

Museums Parks Outdoors

Side Trips

Plymouth, Sandwich, Bourne, Edgartown, New Bedford Whaling Museum
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum
Plimoth Plantation ©
Plimoth Plantation

4
nights
Westfield

Westfield ©
Westfield is a city in Hampden County, in the Pioneer Valley of western Massachusetts, United States. Explore the numerous day-trip ideas around Westfield: Norman Rockwell Museum (in Stockbridge), Smith College Botanic Garden (in Northampton) and Chester Railway Station (in Chester). There's still lots to do: walk around Stanley park, sample the tasty concoctions at Iron Duke Brewing, browse the collection at Amherst Public Library, and explore the world behind art at The Clark Art Institute.

To see ratings, photos, maps, and more tourist information, refer to the Westfield trip itinerary app.

Drive from Falmouth to Westfield in 2.5 hours. When traveling from Falmouth in May, plan for a bit warmer days and about the same nights in Westfield: temperatures range from °F by day to °F at night. Finish your sightseeing early on the 23rd (Sat) so you can travel back home.

Things to do in Westfield

Museums Parks Fun & Games

Side Trips

Dr. Seuss National Memorial Sculpture Garden, Fenway Golf, Amherst Public Library, The Clark Art Institute, Iron Duke Brewing
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Stanley park ©
Stanley park
The Clark Art Institute ©
The Clark Art Institute

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