31 days in Massachusetts Itinerary

31 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner

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Route & dates

31 days in Massachusetts Itinerary

Start: Melbourne
Fly:  26 h
1
Boston
— 10 nights
Drive:  1 h 45 min
2
Westfield
— 3 nights
Drive:  2 h 30 min
3
Sandwich
— 8 nights
Drive:  1 h 15 min
4
Provincetown
— 7 nights
Fly:  27 h
End: Melbourne

10
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 Walden Pond State Reservation (in Concord). There's lots more to do: admire the natural beauty at Boston Public Garden, get up close and personal with brilliant marine life at New England Aquarium, examine the collection at John F. Kennedy Presidential Museum & Library, and appreciate the extensive heritage of Freedom Trail.

For more things to do, where to stay, traveler tips, and other tourist information, you can read our Boston route planning website .

Melbourne, Australia to Boston is an approximately 26-hour flight. You can also do a combination of bus and flight; or do a combination of flight and ferry. The time zone difference when traveling from Melbourne to Boston is minus 15 hours. In May, plan for daily highs up to 22°C, and evening lows to 11°C. Finish your sightseeing early on the 11th (Mon) so you can travel to Westfield.

Things to do in Boston

Museums Parks Historic Sites

Side Trips

Salem, Concord, Cambridge, Buckman Tavern, Brookline Booksmith
Find places to stay May 1 — 11:
Highlights from your plan
Boston Public Garden ©
Boston Public Garden
Museum of Science ©
Museum of Science
New England Aquarium ©
New England Aquarium

3
nights
Westfield

Westfield ©
Westfield is a city in Hampden County, in the Pioneer Valley of western Massachusetts, United States. Change things up with these side-trips from Westfield: Fenway Golf (in East Longmeadow), Village Bike Rentals (in Adams) and Norman Rockwell Museum (in Stockbridge). And it doesn't end there: walk around Stanley park, pause for some photo ops at Dr. Seuss National Memorial Sculpture Garden, see human ingenuity at work at Barre Falls Dam, and find something for the whole family at Six Flags New England.

For photos, traveler tips, ratings, and tourist information, go to the Westfield attractions planning app .

You can drive from Boston to Westfield in 2 hours. In May, plan for daily highs up to 26°C, and evening lows to 10°C. Finish your sightseeing early on the 14th (Thu) so you can travel to Sandwich.

Things to do in Westfield

Parks Outdoors Trails

Side Trips

Springfield, Barre Falls Dam, Mass Central Rail Trail, Swift River Reservation, Village Bike Rentals
Find places to stay May 11 — 14:
Highlights from your plan
Stanley park ©
Stanley park
Six Flags New England ©
Six Flags New England
Village Bike Rentals ©
Village Bike Rentals

8
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Venture out of the city with trips to New Bedford Whaling Museum (in New Bedford), Chatham (Monomoy National Wildlife Refuge & Chatham Lighthouse Beach) and Nickerson State Park (in Brewster). The adventure continues: explore the landscape on two wheels at Shining Sea Bikeway, hike along Cape Cod Rail Trail, enjoy the sand and surf at Craigville Beach, and have some family-friendly fun at Grand Slam Entertainment, Cape Cod Baseball & Bumper Boats.

To see reviews, other places to visit, and more tourist information, read our Sandwich travel planner.

Traveling by car from Westfield to Sandwich takes 2.5 hours. Traveling from Westfield in May, you will find days in Sandwich are little chillier (21°C), and nights are about the same (9°C). Finish up your sightseeing early on the 22nd (Fri) so you can go by car to Provincetown.

Things to do in Sandwich

Parks Outdoors Museums

Side Trips

Plymouth, Falmouth, Yarmouth Port, Chatham, Craigville Beach
Find places to stay May 14 — 22:
Highlights from your plan
Nickerson State Park ©
Nickerson State Park
Plimoth Plantation ©
Plimoth Plantation
Cape Cod Rail Trail ©
Cape Cod Rail Trail

7
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.
Get out of town with these interesting Provincetown side-trips: Nauset Inlet (in Orleans), Eastham (Salt Pond Visitor Center & Coast Guard Beach) and Chatham (Eldredge Public Library, Atwood Museum, &more). The adventure continues: enjoy the sand and surf at Cape Cod National Seashore, tour the pleasant surroundings at Herring Cove Beach, explore the world behind art at Provincetown Art Association and Museum, and appreciate the history behind Pilgrim Monument & Provincetown Museum.

For photos and tourist information, refer to the Provincetown online visit planner .

Traveling by car from Sandwich to Provincetown takes 1.5 hours. Alternatively, you can take a bus. In May, daily temperatures in Provincetown can reach 20°C, while at night they dip to 10°C. Cap off your sightseeing on the 29th (Fri) early enough to travel back home.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Chatham, Eastham, Wellfleet, Nauset Inlet, Cape Cod National Seashore
Find places to stay May 22 — 29:
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach
Herring Cove Beach ©
Herring Cove Beach

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