60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts itinerary maker

Plan created by another user.Make it yours

Route & dates

Start: Boston
1
Boston
— 28 nights
Ferry:  2 h 15 min
2
Provincetown
— 7 nights
Drive:  1 h 15 min
3
Sandwich
— 6 nights
Taxi + Ferry:  1 h 30 min
4
Oak Bluffs, Martha's Vineyard
— 5 nights
Ferry:  2 h 30 min
5
Nantucket
— 7 nights
Ferry + Drive:  5 h 15 min
6
Lenox
— 6 nights
Drive:  2 h 30 min
End: Boston

28
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.
Change things up with these side-trips from Boston: Codman Community Farms (in Lincoln), Independence Park (in Beverly) and Salem (Pickering Wharf, Salem Witch Museum, &more). 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

Historic Sites Museums Parks

Side Trips

Salem, Cambridge, Concord, Woburn, Lexington
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 ©
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 do a combination of ; 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

Side Trips

Orleans, Eastham, Truro Vineyards of Cape Cod, Cape Cod National Seashore
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. Change things up with these side-trips from Sandwich: Public library Hyannis (in Hyannis), Mayflower Cranberries (in Plympton) and Cape Cod Maritime Museum (in Hyannis Port). And it doesn't end there: examine the collection at Sandwich Glass Museum, don't miss a visit to Old King's Hwy, experience rural life at Coonamessett Farm, and grab your bike and head to Shining Sea Bikeway.

For more things to do, traveler tips, where to stay, and other tourist information, read Sandwich attractions app.

Getting from Provincetown to Sandwich by car takes about 1.5 hours. Other options: take a bus. In November, plan for daily highs up to 53°F, and evening lows to 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 Parks Historic Sites

Side Trips

Plymouth, Falmouth, Hyannis, New Bedford, Cape Cod Canal
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). There's lots more to do: contemplate the long history of Trinity Park Tabernacle, walk around Ocean Park, make a trip to Flying Horses Carousel, and relax in the rural setting at The Farm Institute.

To see ratings, more things to do, photos, and more tourist information, go to the Oak Bluffs trip maker app.

You can do a combination of taxi and ferry from Sandwich to Oak Bluffs in 1.5 hours. Another option is to drive. In November, daily temperatures in Oak Bluffs can reach 53°F, while at night they dip to 37°F. Wrap up your sightseeing on the 16th (Mon) to allow time to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Historic Sites Parks Outdoors

Side Trips

Edgartown, Aquinnah, West Tisbury, Cape Poge Wildlife Refuge, The Grey Barn
Highlights from your plan
Trinity Park Tabernacle ©
Trinity Park Tabernacle
Farm Neck Golf Club ©
Farm Neck Golf Club
Flying Horses Carousel ©
Flying Horses Carousel

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, play a few rounds at Miacomet Golf Club, kick back and relax at Jetties Beach, and get engrossed in the history at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To see ratings, other places to visit, photos, and more tourist information, read Nantucket trip planner.

Traveling by ferry from Oak Bluffs to Nantucket takes 2 hours. In November, daytime highs in Nantucket are 53°F, while nighttime lows are 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
Highlights from your plan
Moors End Farm ©
Moors End Farm
Miacomet Golf Club ©
Miacomet Golf Club

6
nights
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Change things up with these side-trips from Lenox: Westfield (Amelia Park Children's Museum & Stanley park), Adams (Mount Greylock & Ashuwillticook Rail Trail) and Chester Railway Station (in Chester). 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, relax in the rural setting at Bartlett's Orchard, and contemplate in the serene atmosphere at National Shrine of the Divine Mercy.

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 take a 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

Side Trips

Stockbridge, Pittsfield, Westfield, Adams, The Clark Art Institute
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

Similar Plans

33 days in United States BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: July, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 11 days in Massachusetts BY A USER FROM UNITED STATES June, outdoors, relaxing, romantic, historic sites, museums, shopping, popular sights Preferences: June, outdoors, relaxing, romantic, historic sites, museums, shopping Attraction style: Popular sights Pace: Medium 3 days in Massachusetts BY A USER FROM UNITED STATES July, teens, kids, outdoors, relaxing, beaches, shopping, popular sights Preferences: July, teens, kids, outdoors, relaxing, beaches, shopping Attraction style: Popular sights Pace: Medium 7 days in United States BY A USER FROM UNITED STATES July, culture, relaxing, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: July, culture, relaxing, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 15 days in United States BY A USER FROM UNITED STATES June, teens, culture, outdoors, beaches, historic sites, museums, wildlife, popular sights Preferences: June, teens, culture, outdoors, beaches, historic sites, museums, wildlife Attraction style: Popular sights Pace: Medium 11 days in Massachusetts, Rhode Island & Connecticut BY A USER FROM UNITED STATES September, outdoors, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: September, outdoors, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 10 days in Massachusetts, Rhode Island & Connecticut BY A USER FROM UNITED STATES September, outdoors, historic sites, museums, shopping, wildlife, popular sights Preferences: September, outdoors, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 14 days in United States BY A USER FROM UNITED STATES June, teens, culture, relaxing, historic sites, slow & easy, popular & hidden gems Preferences: June, teens, culture, relaxing, historic sites Attraction style: Popular & hidden gems Pace: Slow & easy 10 days in United States BY A USER FROM UNITED STATES September, outdoors, historic sites, museums, shopping, wildlife, popular sights Preferences: September, outdoors, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 15 days in United States BY A USER FROM UNITED STATES July, outdoors, historic sites, museums, wildlife, popular sights Preferences: July, outdoors, historic sites, museums, wildlife Attraction style: Popular sights Pace: Medium 20 days in Massachusetts & New York City BY A USER FROM TAIWAN May, culture, relaxing, historic sites, popular sights Preferences: May, culture, relaxing, historic sites Attraction style: Popular sights Pace: Medium
See more plans