43 days in Massachusetts Itinerary

43 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

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Route & dates

43 days in Massachusetts Itinerary

Start: Fortaleza
Fly:  17​h
1
Provincetown
— 6 nights
Drive:  1​h 15​min
2
Sandwich
— 7 nights
Drive:  1​h 30​min
3
Oak Bluffs, Martha's Vineyard
— 6 nights
Drive:  2​h 30​min
4
Nantucket
— 6 nights
ferry + Drive:  4​h 30​min
5
Stockbridge
— 7 nights
Drive:  2​h 30​min
6
Boston
— 8 nights
Fly:  15​h 15​min
End: Fortaleza

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.
You'll find plenty of places to visit near Provincetown: Nauset Beach (in Orleans) and Eastham (Nauset Light Beach, Salt Pond Visitor Center, & more). Next up on the itinerary: appreciate the history behind Pilgrim Monument & Provincetown Museum, make a trip to Commercial Street, get lost in a book at Provincetown Library, and enjoy the sand and surf at Cape Cod National Seashore.

To see maps, where to stay, photos, and other tourist information, go to the Provincetown trip builder site .

Fortaleza, Brazil to Provincetown is an approximately 17-hour flight. You can also do a combination of flight and ferry; or do a combination of flight and bus. The time zone difference moving from Brasilia Time (BRT) to Eastern Standard Time (EST) is minus 2 hours. In September, Provincetown is a bit cooler than Fortaleza - with highs of 25°C and lows of 16°C. Wrap up your sightseeing on the 30th (Mon) to allow time to drive to Sandwich.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Eastham, Wellfleet, Truro, Cape Cod National Seashore, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach

7
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Venture out of the city with trips to Chatham Marconi Maritime Center (in North Chatham), Grand Slam Entertainment, Cape Cod Baseball & Bumper Boats (in Harwich Port) and Falmouth (Highfield Hall & Gardens & Cornelia Carey Sanctuary (The Knob)). The adventure continues: see the interesting displays at Heritage Museums & Gardens, stroll through Shining Sea Bikeway, trek along Cape Cod Rail Trail, and don't miss a visit to Old King's Hwy.

To find maps, where to stay, traveler tips, and tourist information, use the Sandwich itinerary builder app .

You can drive from Provincetown to Sandwich in 1.5 hours. Another option is to take a bus. In September in Sandwich, expect temperatures between 26°C during the day and 15°C at night. Cap off your sightseeing on the 7th (Mon) early enough to go by car to Oak Bluffs.

Things to do in Sandwich

Parks Museums Outdoors

Side Trips

Plymouth, Falmouth, Chatham, Hyannis, Yarmouth Port
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation

6
nights
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Change things up with these side-trips from Oak Bluffs: Menemsha Hills (in Chilmark) and Menemsha Public Beach (in Menemsha). And it doesn't end there: admire the striking features of Trinity Park Tabernacle, tee off at Farm Neck Golf Club, don't miss a visit to Flying Horses Carousel, and take a stroll through Martha's Vineyard Camp meeting Association (MVCMA).

For maps, other places to visit, reviews, and other tourist information, read Oak Bluffs sightseeing tool .

Drive from Sandwich to Oak Bluffs in 1.5 hours. In October, plan for daily highs up to 21°C, and evening lows to 9°C. Cap off your sightseeing on the 13th (Sun) early enough to go by car to Nantucket.

Things to do in Oak Bluffs

Parks Outdoors Beaches

Side Trips

Edgartown, West Tisbury, Chilmark, Menemsha Public Beach, Aquinnah Cliffs
Highlights from your plan
Mytoi ©
Mytoi
Trinity Park Tabernacle ©
Trinity Park Tabernacle
Farm Neck Golf Club ©
Farm Neck Golf Club

6
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, historic sites, breweries & distilleries, and outdoors. Your plan includes some of its best attractions: examine the collection at Whaling Museum, tee off at Miacomet Golf Club, kick back and relax at Jetties Beach, and appreciate the extensive heritage of Milestone Bog.

For traveler tips, where to stay, and other tourist information, read our Nantucket trip planner.

You can drive from Oak Bluffs to Nantucket in 2.5 hours. In October, daily temperatures in Nantucket can reach 20°C, while at night they dip to 12°C. Finish up your sightseeing early on the 19th (Sat) so you can travel to Stockbridge.

Things to do in Nantucket

Outdoors Parks Historic Sites
Highlights from your plan
Madaket Beach ©
Madaket Beach
Whaling Museum ©
Whaling Museum
Great Point Light ©
Great Point Light

7
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Get out of town with these interesting Stockbridge side-trips: Zipline (in Charlemont), Silvio O. Conte National Fish and Wildlife Refuge (in Hadley) and Bridge of Flowers (in Shelburne Falls). The adventure continues: admire the masterpieces at Norman Rockwell Museum, steep yourself in history at The Mount, Edith Wharton's Home, stroll around Stanley park, and admire the natural beauty at Grandmother's Garden.

For ratings, traveler tips, maps, and more tourist information, use the Stockbridge trip itinerary planner.

Do a combination of ferry and car from Nantucket to Stockbridge in 4.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of ferry and bus. Traveling from Nantucket in October, expect slightly colder with lows of 5°C in Stockbridge. Cap off your sightseeing on the 26th (Sat) early enough to go by car to Boston.

Things to do in Stockbridge

Parks Museums Outdoors

Side Trips

Westfield, Pittsfield, Williamstown, The Mount, Edith Wharton's Home, Pocumtuck Ridge
Highlights from your plan
Stanley park ©
Stanley park
Norman Rockwell Museum ©
Norman Rockwell Museum
The Clark Art Institute ©
The Clark Art Institute

8
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.
Explore the numerous day-trip ideas around Boston: Dolphin & Whale Watching (in Gloucester) and Salem (Salem Witch Museum, The House of the Seven Gables, & more). There's lots more to do: admire the masterpieces at Museum of Fine Arts, admire the natural beauty at Boston Public Garden, wander the streets of North End, and buy something for everyone on your list at Faneuil Hall Marketplace.

To see reviews, other places to visit, ratings, and other tourist information, refer to the Boston attractions planning tool .

You can drive from Stockbridge to Boston in 2.5 hours. Alternatively, you can take a bus; or take a train. Plan for somewhat warmer nights when traveling from Stockbridge in October since evenings lows in Boston dip to 11°C. Wrap up your sightseeing on the 3rd (Sun) to allow time to travel back home.

Things to do in Boston

Museums Historic Sites Tours

Side Trips

Salem, Cambridge, The Telephone Museum, Dolphin & Whale Watching, Louisa May Alcott's Orchard House
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Dolphin & Whale Watching

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