60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts itinerary maker

Plan created by another user. Make it yours
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Boston
— 28 nights
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Provincetown
— 7 nights
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Sandwich
— 6 nights
4
Oak Bluffs, Martha's Vineyard
— 5 nights
5
Nantucket
— 7 nights
6
Lenox
— 6 nights

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28
nights
Boston

Boston ©

Beantown

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.
Change things up with these side-trips from Boston: Independence Park (in Beverly), Salem (Salem Witch Museum, The House of the Seven Gables, &more) and Codman Community Farms (in Lincoln). There's much more to do: explore the world behind art at Museum of Fine Arts, admire the natural beauty at Boston Public Garden, make a trip to Faneuil Hall Marketplace, and get to know the fascinating history of Freedom Trail.

To plan Boston vacation without wasting time, ask Inspirock to design an itinerary.

Use the Route module to see travel options from your home to Boston. In October, plan for daily highs up to 64°F, and evening lows to 50°F. Wrap up your sightseeing on the 29th (Thu) to allow time to ride a ferry to Provincetown.

Things to do in Boston

Side Trips

Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

7
nights
Provincetown

Provincetown ©

Birthplace of American Liberty

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.
Venture out of the city with trips to Orleans (Nauset Inlet, Addison Art Gallery, &more) and Eastham (Nauset Light Beach, Salt Pond Visitor Center, &more). There's lots more to do: kick back and relax at Cape Cod National Seashore, tour the pleasant surroundings at Race Point Beach, appreciate the history behind Pilgrim Monument & Provincetown Museum, and browse the collection at Provincetown Library.

To find maps, more things to do, other places to visit, and more tourist information, refer to the Provincetown road trip website.

You can ride a ferry from Boston to Provincetown in 2.5 hours. Alternatively, you can fly; or drive. October in Provincetown sees daily highs of 63°F and lows of 49°F at night. Wrap up your sightseeing on the 5th (Thu) early enough to drive to Sandwich.

Things to do in Provincetown

Parks · Outdoors · Beaches · Museums

Side Trips

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
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Get out of town with these interesting Sandwich side-trips: New Bedford (Hurricane Barrier Harbor Walk & New Bedford Whaling Museum), Mayflower Cranberries (in Plympton) and Stone Bridge Farm (in Acushnet). There's lots more to do: get curious at Sandwich Glass Museum, browse the exhibits of Highfield Hall & Gardens, see the interesting displays at Heritage Museums & Gardens, and visit a coastal fixture at Nobska Point Lighthouse.

For photos, ratings, maps, and other tourist information, use the Sandwich online vacation planner.

Drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 53°F in November, and nighttime lows around 35°F. Finish your sightseeing early on the 11th (Wed) to allow enough time to travel to Oak Bluffs.

Things to do in Sandwich

Museums · Historic Sites · Parks · Trails

Side Trips

Highlights from your plan
Sandwich Glass Museum ©
Sandwich Glass Museum
Old King's Hwy ©
Old King's Hwy
Plimoth Plantation ©
Plimoth Plantation

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 the numerous day-trip ideas around Oak Bluffs: Aquinnah (Gay Head Lighthouse & Aquinnah Lighthouse). Next up on the itinerary: steep yourself in history at Trinity Park Tabernacle, look for all kinds of wild species at Sheriff's Meadow Sanctuary, visit Martha's Vineyard Camp meeting Association (MVCMA), and walk around Ocean Park.

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

You can do a combination of taxi and ferry from Sandwich to Oak Bluffs in 1.5 hours. In November in Oak Bluffs, expect temperatures between 53°F during the day and 37°F at night. Wrap up your sightseeing on the 16th (Mon) early enough to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Historic Sites · Parks · Neighborhoods · Wildlife

Side Trips

Highlights from your plan
Trinity Park Tabernacle ©
Trinity Park Tabernacle
Farm Neck Golf Club ©
Farm Neck Golf Club

7
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: enjoy the sea views from Great Point Light, tee off at Miacomet Golf Club, examine the collection at Nantucket Lightship Basket Museum, and take an in-depth tour of Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

For photos, where to stay, ratings, and other tourist information, refer to the Nantucket itinerary maker site.

Getting from Oak Bluffs to Nantucket by ferry takes about 2 hours. Expect a daytime high around 53°F in November, and nighttime lows around 41°F. Finish up your sightseeing early on the 23rd (Mon) so you can travel to Lenox.

Things to do in Nantucket

Historic Sites · Parks · Outdoors · Beaches
Highlights from your plan
Miacomet Golf Club ©
Miacomet Golf Club
Moors End Farm ©
Moors End Farm

6
nights
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Change things up with these side-trips from Lenox: Chester Railway Station (in Chester), Adams (Mount Greylock & Ashuwillticook Rail Trail) and Westfield (Amelia Park Children's Museum & Stanley park). There's still lots to do: explore the world behind art at Norman Rockwell Museum, take your sightseeing to a higher altitude at Monument Mountain, take in the spiritual surroundings of National Shrine of the Divine Mercy, and experience rural life at Bartlett's Orchard.

To see traveler tips, ratings, maps, and more tourist information, read Lenox trip builder website.

You can do a combination of ferry and car from Nantucket to Lenox in 5.5 hours. Other options are to do a combination of flight and bus; or do a combination of ferry and bus. Plan for slightly colder temperatures traveling from Nantucket in November, with highs in Lenox at 47°F and lows at 28°F. Wrap up your sightseeing on the 29th (Sun) early enough to drive back home.

Things to do in Lenox

Museums · Parks · Historic Sites · Nature

Side Trips

Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
The Clark Art Institute ©
The Clark Art Institute
The Mount, Edith Wharton's Home ©
The Mount, Edith Wharton's Home

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