60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts travel route builder

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Route & dates

60 days in Massachusetts Itinerary

Start: Gdansk
Fly:  13​h
1
Boston
— 13 nights
Drive:  2​h 30​min
2
Lenox
— 10 nights
Drive + ferry:  4​h 30​min
3
Nantucket
— 10 nights
Drive:  2​h 30​min
4
Oak Bluffs, Martha's Vineyard
— 8 nights
Drive:  1​h 30​min
5
Sandwich
— 9 nights
Drive:  1​h 15​min
6
Provincetown
— 8 nights
Fly:  15​h
End: Gdansk

13
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 Boston's surroundings by going to Gloucester (Dolphin & Whale Watching & Niles Beach), Salem (Peabody Essex Museum, Witch Pix, & more) and Essex Shipbuilding Museum (in Essex). The adventure continues: admire all the interesting features of Fenway Park, take an in-depth tour of John F. Kennedy Presidential Museum & Library, appreciate the extensive heritage of Freedom Trail, and walk around Boston Common.

To see ratings, other places to visit, maps, and other tourist information, go to the Boston trip itinerary maker .

Gdansk, Poland to Boston is an approximately 13-hour flight. You can also do a combination of train and flight. Traveling from Gdansk to Boston, you'll gain 6 hours due to the time zone difference. Expect a bit warmer temperatures when traveling from Gdansk in June; daily highs in Boston reach 28°C and lows reach 18°C. Finish your sightseeing early on the 7th (Sun) so you can drive to Lenox.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Cambridge, Gloucester, Needham, Concord
Highlights from your plan
Freedom Trail ©
Freedom Trail
Fenway Park ©
Fenway Park
Museum of Fine Arts ©
Museum of Fine Arts

10
nights
Lenox

Lenox ©
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Venture out of the city with trips to Westfield (Grandmother's Garden & Stanley park), The Clark Art Institute (in Williamstown) and Tannery Falls (in Savoy). Next up on the itinerary: explore the world behind art at Norman Rockwell Museum, contemplate the long history of The Mount, Edith Wharton's Home, take in the dramatic scenery at Bash Bish Falls, and take your sightseeing to a higher altitude at Lenox Mountain.

To see other places to visit, maps, ratings, and other tourist information, you can read our Lenox trip planner .

Drive from Boston to Lenox in 2.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in July, plan for little chillier nights in Lenox, with lows around 17°C. Finish your sightseeing early on the 17th (Wed) to allow enough time to travel to Nantucket.

Things to do in Lenox

Parks Nature Museums

Side Trips

Stockbridge, North Adams, Sheffield, Westfield, Lee
Highlights from your plan
Stanley park ©
Stanley park
The Clark Art Institute ©
The Clark Art Institute
Norman Rockwell Museum ©
Norman Rockwell Museum

10
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: see the interesting displays at Whaling Museum, admire the natural beauty at Oldest House (Jethro Coffin House) and Kitchen Garden, get to know the fascinating history of Milestone Bog, and visit a coastal fixture at Great Point Light.

To see photos, maps, and more tourist information, refer to the Nantucket day trip planner .

Traveling by combination of car and ferry from Lenox to Nantucket takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and ferry. In July, daytime highs in Nantucket are 28°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 27th (Sat) to allow time to drive to Oak Bluffs.

Things to do in Nantucket

Parks Historic Sites Outdoors
Highlights from your plan
Jetties Beach ©
Jetties Beach
Whaling Museum ©
Whaling Museum
Miacomet Golf Club ©
Miacomet Golf Club

8
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. Get out of town with these interesting Oak Bluffs side-trips: Menemsha Public Beach (in Menemsha), Chilmark (Chilmark Chocolates & Lucy Vincent Beach) and Aquinnah (Gay Head & Gay Head Lighthouse). There's lots more to do: play a few rounds at Farm Neck Golf Club, take a stroll through West Chop, admire the landmark architecture of Trinity Park Tabernacle, and kick back and relax at Joseph Sylvia State Beach.

To see other places to visit, reviews, more things to do, and tourist information, read our Oak Bluffs holiday website .

Traveling by car from Nantucket to Oak Bluffs takes 2.5 hours. In July in Oak Bluffs, expect temperatures between 30°C during the day and 20°C at night. Wrap up your sightseeing on the 4th (Sun) to allow time to drive to Sandwich.

Things to do in Oak Bluffs

Parks Outdoors Beaches

Side Trips

West Tisbury, Chilmark, Aquinnah, Vineyard Haven Public Library, Menemsha Public Beach
Highlights from your plan
Cedar Tree Neck Sanctuary ©
Cedar Tree Neck Sanctuary
Farm Neck Golf Club ©
Farm Neck Golf Club
Flying Horses Carousel ©
Flying Horses Carousel

9
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Explore the numerous day-trip ideas around Sandwich: Yarmouth Port (Captain Bangs Hallet House Museum & Edward Gorey House), Falmouth (Highfield Hall & Gardens, Spohr Gardens, & more) and Chatham (Chatham Lighthouse Beach & Monomoy National Wildlife Refuge). The adventure continues: see the interesting displays at Heritage Museums & Gardens, appreciate the history behind Plymouth Rock, tour the pleasant surroundings at Old Silver Beach, and explore the landscape on two wheels at Shining Sea Bikeway.

To see maps, ratings, where to stay, and more tourist information, refer to the Sandwich trip itinerary builder site .

Getting from Oak Bluffs to Sandwich by car takes about 1.5 hours. In August in Sandwich, expect temperatures between 30°C during the day and 19°C at night. Cap off your sightseeing on the 13th (Tue) early enough to go by car to Provincetown.

Things to do in Sandwich

Parks Outdoors Museums

Side Trips

Falmouth, Plymouth, Yarmouth Port, Hyannis, Chatham
Highlights from your plan
Shining Sea Bikeway ©
Shining Sea Bikeway
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum

8
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.
Explore the numerous day-trip ideas around Provincetown: Chatham Marconi Maritime Center (in North Chatham), Chatham Railroad Museum (in Chatham) and Nauset Beach (in Orleans). And it doesn't end there: pause for some photo ops at Pilgrim Monument & Provincetown Museum, kick back and relax at Marconi Beach, stroll through Race Point Beach, and trek along Cape Cod Rail Trail.

To find ratings, other places to visit, traveler tips, and tourist information, use the Provincetown day trip planning site .

You can drive from Sandwich to Provincetown in 1.5 hours. Alternatively, you can take a bus. In August, daily temperatures in Provincetown can reach 30°C, while at night they dip to 19°C. Finish your sightseeing early on the 21st (Wed) so you can travel back home.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Eastham, Wellfleet, Chatham, Cape Cod, Nauset Beach
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach

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