57 days in Massachusetts Itinerary

57 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

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Route & dates

57 days in Massachusetts Itinerary

Start: Rio de Janeiro
Fly:  15​h 30​min
1
Provincetown
— 9 nights
Drive:  1​h 15​min
2
Sandwich
— 9 nights
Drive:  1​h 30​min
3
Oak Bluffs, Martha's Vineyard
— 7 nights
Drive:  2​h 30​min
4
Nantucket
— 9 nights
ferry + Drive:  4​h 30​min
5
Stockbridge
— 9 nights
Drive:  2​h 30​min
6
Boston
— 12 nights
Fly:  16​h
End: Rio de Janeiro

9
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.
Family-friendly places like Cape Cod National Seashore and Race Point Beach will thrill your kids. Get out of town with these interesting Provincetown side-trips: Nauset Beach (in Orleans), Eastham (Coast Guard Beach, First Encounter Beach, & more) and Chatham's Godfrey Windmill (in Chatham). The adventure continues: appreciate the history behind Pilgrim Monument & Provincetown Museum, make a trip to Commercial Street, kick back and relax at Corn Hill Beach, and take a leisurely stroll along MacMillan Wharf.

For where to stay, more things to do, traveler tips, and other tourist information, refer to the Provincetown trip itinerary builder website .

Rio de Janeiro, Brazil to Provincetown is an approximately 15.5-hour flight. You can also do a combination of flight and ferry; or do a combination of flight and bus. The time zone difference when traveling from Rio de Janeiro to Provincetown is minus 2 hours. Prepare for slightly colder weather when traveling from Rio de Janeiro in September: high temperatures in Provincetown hover around 25°C and lows are around 16°C. Wrap up your sightseeing on the 16th (Mon) to allow time to drive to Sandwich.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Wellfleet, Eastham, Truro, Cape Cod National Seashore, Chatham's Godfrey Windmill
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Nauset Beach ©
Nauset Beach
Race Point Beach ©
Race Point Beach

9
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Kids will appreciate attractions like Sandwich Glass Museum and Plymouth Rock. Change things up with these side-trips from Sandwich: Woods Hole (Nobska Point Lighthouse & Woods Hole Science Aquarium), Falmouth (Cornelia Carey Sanctuary (The Knob) & Highfield Hall & Gardens) and Chatham (Chatham Lighthouse Beach & Monomoy National Wildlife Refuge). And it doesn't end there: take an in-depth tour of Plimoth Plantation, steep yourself in history at Mayflower II, make a trip to Old King's Hwy, and kick back and relax at Old Silver Beach.

For more things to do, traveler tips, photos, and more tourist information, refer to the Sandwich online tour planner .

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 26°C, and evening lows to 15°C. Wrap up your sightseeing on the 25th (Wed) early enough to drive to Oak Bluffs.

Things to do in Sandwich

Parks Museums Outdoors

Side Trips

Falmouth, Plymouth, Chatham, Yarmouth Port, South Yarmouth
Highlights from your plan
Old Silver Beach ©
Old Silver Beach
Plimoth Plantation ©
Plimoth Plantation
Sandwich Glass Museum ©
Sandwich Glass Museum

7
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. You'll visit kid-friendly attractions like Flying Horses Carousel and Norton Point Beach. You'll find plenty of places to visit near Oak Bluffs: Chilmark (Menemsha Hills & Lucy Vincent Beach), Gay Head Lighthouse (in Aquinnah) and Menemsha Public Beach (in Menemsha). There's lots more to do: contemplate the long history of Trinity Park Tabernacle, kick back and relax at Lighthouse Beach, tee off at Farm Neck Golf Club, and stroll through Joseph Sylvia State Beach.

To see where to stay, photos, ratings, and more tourist information, read our Oak Bluffs online trip planner .

Traveling by car from Sandwich to Oak Bluffs takes 1.5 hours. Expect a daytime high around 27°C in September, and nighttime lows around 14°C. Cap off your sightseeing on the 2nd (Wed) early enough to go by car to Nantucket.

Things to do in Oak Bluffs

Parks Outdoors Beaches

Side Trips

Edgartown, West Tisbury, Aquinnah, Chilmark, Menemsha Public Beach
Highlights from your plan
Menemsha Hills ©
Menemsha Hills
Flying Horses Carousel ©
Flying Horses Carousel
Menemsha Public Beach ©
Menemsha Public Beach

9
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Attractions like Jetties Beach and Surfside Beach make great kid-friendly stops. Next up on the itinerary: see the interesting displays at Whaling Museum, learn about winemaking at Cisco Brewers, enjoy the sea views from Great Point Light, and take an in-depth tour of Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

For traveler tips, reviews, more things to do, and more tourist information, refer to the Nantucket trip itinerary maker app .

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 your sightseeing early on the 11th (Fri) to allow enough time to travel to Stockbridge.

Things to do in Nantucket

Outdoors Parks Historic Sites
Highlights from your plan
Madaket Beach ©
Madaket Beach
Fishing Charters & Tours
Cisco Beach ©
Cisco Beach

9
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Kids will appreciate attractions like Stanley park and Holyoke Children's Museum. You'll find plenty of places to visit near Stockbridge: Springfield (Basketball Hall of Fame, MGM Springfield, & more), Grandmother's Garden (in Westfield) and Six Flags New England (in Agawam). There's much more to do: explore the world behind art at Norman Rockwell Museum, experience rural life at Hancock Shaker Village, get interesting insight from Tours, and admire the majestic nature at Mount Greylock State Reservation.

To see more things to do, ratings, and tourist information, you can read our Stockbridge trip planner .

Traveling by combination of ferry and car from Nantucket to Stockbridge takes 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. Wrap up your sightseeing on the 20th (Sun) early enough to drive to Boston.

Things to do in Stockbridge

Parks Museums Outdoors

Side Trips

Springfield, Pittsfield, Williamstown, Lee, Westfield
Highlights from your plan
Stanley park ©
Stanley park
Six Flags New England ©
Six Flags New England
Jiminy Peak Mountain Resort ©
Jiminy Peak Mountain Resort

12
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.
You'll visit kid-friendly attractions like Museum of Fine Arts and Faneuil Hall Marketplace. Get out of town with these interesting Boston side-trips: Front Beach (in Rockport), Salem (Peabody Essex Museum, Salem Witch Museum, & more) and Dolphin & Whale Watching (in Gloucester). The adventure continues: take in nature's colorful creations at Boston Public Garden, get curious at Museum of Science, get engrossed in the history at USS Constitution Museum, and admire nature's wide array of creatures at New England Aquarium.

To see traveler tips, reviews, other places to visit, and tourist information, read our Boston road trip planning website .

You can drive from Stockbridge to Boston in 2.5 hours. Other options are to 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. Finish your sightseeing early on the 1st (Fri) to allow enough time to travel back home.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Cambridge, Concord, Dolphin & Whale Watching, Front Beach
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
New England Aquarium ©
New England Aquarium

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