32 days in Massachusetts Itinerary

32 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour planner

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Route & dates

32 days in Massachusetts Itinerary

Start: Newark
+2
Fly + foot + bus:  4​h 30​min
1
Sandwich
— 6 nights
Drive:  1​h 15​min
2
Provincetown
— 5 nights
Drive:  2​h 45​min
3
Oak Bluffs, Martha's Vineyard
— 5 nights
Drive:  2​h 30​min
4
Nantucket
— 6 nights
ferry + Drive:  2​h 30​min
5
Boston
— 9 nights
Fly:  3​h
End: Newark

6
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Get out of town with these interesting Sandwich side-trips: Chatham Marconi Maritime Center (in North Chatham), Falmouth (Cornelia Carey Sanctuary (The Knob), Highfield Hall & Gardens, & more) and Yarmouth Port (Captain Bangs Hallet House Museum & Edward Gorey House). Next up on the itinerary: see the interesting displays at Heritage Museums & Gardens, explore the landscape on two wheels at Shining Sea Bikeway, don't miss a visit to Old King's Hwy, and kick back and relax at Chatham Lighthouse Beach.

To see maps, where to stay, and tourist information, go to the Sandwich online route planner .

Newark to Sandwich is an approximately 4.5-hour combination of flight and bus. You can also drive; or do a combination of train, flight, and bus. Traveling from Newark in September, expect Sandwich to be slightly colder, temps between 73°F and 55°F. Finish up your sightseeing early on the 3rd (Thu) so you can go by car to Provincetown.

Things to do in Sandwich

Parks Museums Outdoors

Side Trips

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

5
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: Eastham (Nauset Light Beach, Coast Guard Beach, & more) and Orleans (Nauset Beach & Addison Art Gallery). There's lots more to do: explore the galleries of Pilgrim Monument & Provincetown Museum, browse the collection at Provincetown Library, enjoy the sand and surf at Race Point Beach, and stroll through Herring Cove Beach.

To find ratings, other places to visit, and tourist information, use the Provincetown visit app .

You can drive from Sandwich to Provincetown in 1.5 hours. Another option is to take a bus. Expect a daytime high around 63°F in October, and nighttime lows around 49°F. Cap off your sightseeing on the 8th (Tue) early enough to go by car to Oak Bluffs.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

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

5
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. Explore Oak Bluffs' surroundings by going to Menemsha Hills (in Chilmark) and Gay Head Lighthouse (in Aquinnah). There's much more to do: admire the striking features of Trinity Park Tabernacle, enjoy the sea views from Edgartown Lighthouse, admire the natural beauty at Mytoi, and take in the dramatic natural features at Aquinnah Cliffs.

To see maps, reviews, where to stay, and tourist information, read Oak Bluffs journey builder .

Traveling by car from Provincetown to Oak Bluffs takes 3 hours. October in Oak Bluffs sees daily highs of 65°F and lows of 46°F at night. Finish your sightseeing early on the 13th (Sun) to allow enough time to drive to Nantucket.

Things to do in Oak Bluffs

Parks Outdoors Beaches

Side Trips

Edgartown, West Tisbury, Aquinnah, Chilmark
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, wineries, and outdoors. Your plan includes some of its best attractions: examine the collection at Whaling Museum, enjoy the sand and surf at Madaket Beach, visit a coastal fixture at Great Point Light, and take an in-depth tour of Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To find photos, ratings, reviews, and tourist information, you can read our Nantucket online driving holiday planner .

Drive from Oak Bluffs to Nantucket in 2.5 hours. October in Nantucket sees daily highs of 64°F and lows of 51°F at night. Wrap up your sightseeing on the 19th (Sat) early enough to travel to Boston.

Things to do in Nantucket

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

9
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: Gloucester (Cape Ann Museum & Dolphin & Whale Watching), Old First Parish Burying Ground (in Rockport) and Salem (Peabody Essex Museum, The House of the Seven Gables, & more). There's lots more to do: admire the masterpieces at Museum of Fine Arts, take a stroll through North End, get engrossed in the history at Boston Tea Party Ships & Museum, and get lost in a book at John F. Kennedy Presidential Museum & Library.

To find traveler tips, ratings, more things to do, and tourist information, you can read our Boston trip planner .

Getting from Nantucket to Boston by combination of ferry and car takes about 2.5 hours. Other options: fly; or do a combination of flight and bus. In October in Boston, expect temperatures between 64°F during the day and 50°F at night. Finish your sightseeing early on the 28th (Mon) so you can travel back home.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Cambridge, Gloucester, Old First Parish Burying Ground, 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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