60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts travel route builder

Plan created by another user. Make it yours

Route & dates

1
Boston
— 13 nights
2
Lenox
— 10 nights
3
Nantucket
— 10 nights
4
Oak Bluffs, Martha's Vineyard
— 8 nights
5
Sandwich
— 9 nights
6
Provincetown
— 8 nights

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.
Change things up with these side-trips from Boston: Salem (Peabody Essex Museum, Salem Witch Museum, &more), Gloucester (Dolphin & Whale Watching & Niles Beach) and Essex Shipbuilding Museum (in Essex). There's lots more to do: see where the action happens at Fenway Park, explore the world behind art at Museum of Fine Arts, get to know the fascinating history of Freedom Trail, and get your bearings at John F. Kennedy Presidential Museum & Library.

For more things to do, traveler tips, and more tourist information, refer to the Boston tour itinerary planner.

Gdansk, Poland to Boston is an approximately 12-hour flight. The time zone difference moving from Central European Standard Time (CET) to Eastern Standard Time (EST) is minus 6 hours. Traveling from Gdansk in June, things will get somewhat warmer in Boston: highs are around °C and lows about °C. Wrap up your sightseeing on the 7th (Sun) early enough to drive to Lenox.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Cambridge, Concord, Lexington, Needham
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. Change things up with these side-trips from Lenox: The Clark Art Institute (in Williamstown), Westfield (Grandmother's Garden & Stanley park) and Tannery Falls (in Savoy). There's much more to do: explore the world behind art at Norman Rockwell Museum, tour the pleasant surroundings at Manhan Rail Trail, get lost in a book at Carnegie Public Library, and steep yourself in history at The Mount, Edith Wharton's Home.

To find ratings, reviews, where to stay, and more tourist information, you can read our Lenox trip itinerary builder website.

You can drive from Boston to Lenox in 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect slightly colder evenings in Lenox when traveling from Boston in July, with lows around °C. Wrap up your sightseeing on the 17th (Wed) early enough to travel to Nantucket.

Things to do in Lenox

Parks Nature Museums

Side Trips

Stockbridge, Sheffield, Westfield, Lee, North Adams
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, and historic sites. Your plan includes some of its best attractions: examine the collection at Whaling Museum, enjoy the sea views from Great Point Light, take some stellar pictures from First Congregational Church, and kick back and relax at Jetties Beach.

For traveler tips, other places to visit, more things to do, and other tourist information, go to the Nantucket online route planner.

Do a combination of car and ferry from Lenox to Nantucket in 5.5 hours. Alternatively, you can take a bus; or do a combination of bus and ferry. July in Nantucket sees daily highs of °C and lows of °C at night. Finish your sightseeing early on the 27th (Sat) to allow enough time to ride a ferry to Oak Bluffs.

Things to do in Nantucket

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

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 (Menemsha Hills & Lucy Vincent Beach) and Aquinnah (Gay Head & Gay Head Lighthouse). There's lots more to do: make a trip to Flying Horses Carousel, examine the collection at Cottage Museum, stroll through Beach Road between Oak Bluffs and Edgartown, and look for gifts at Chilmark Chocolates.

For ratings, reviews, maps, and tourist information, use the Oak Bluffs online attractions planner.

Ride a ferry from Nantucket to Oak Bluffs in 2 hours. In July, daytime highs in Oak Bluffs are °C, while nighttime lows are °C. Wrap up your sightseeing on the 4th (Sun) to allow time to travel to Sandwich.

Things to do in Oak Bluffs

Parks Outdoors Beaches

Side Trips

West Tisbury, Chilmark, Aquinnah, Menemsha Public Beach, Vineyard Haven Public Library
Highlights from your plan
Cedar Tree Neck Sanctuary ©
Cedar Tree Neck Sanctuary
Flying Horses Carousel ©
Flying Horses Carousel
Trinity Park Tabernacle ©
Trinity Park Tabernacle

9
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. You'll find plenty of places to visit near Sandwich: Falmouth (Highfield Hall & Gardens & Spohr Gardens), Yarmouth Port (Captain Bangs Hallet House Museum & Edward Gorey House) and Chatham (Chatham Lighthouse Beach & Monomoy National Wildlife Refuge). There's much more to do: examine the collection at Heritage Museums & Gardens, take an in-depth tour of The Jenney, make a trip to Old King's Hwy, and tour the pleasant surroundings at Shining Sea Bikeway.

To find traveler tips, more things to do, and more tourist information, use the Sandwich day trip planning site.

Traveling by combination of ferry and taxi from Oak Bluffs to Sandwich takes 1.5 hours. Alternatively, you can drive. August in Sandwich sees daily highs of °C and lows of °C at night. Finish your sightseeing early on the 13th (Tue) so you can drive to Provincetown.

Things to do in Sandwich

Parks Outdoors Museums

Side Trips

Falmouth, Plymouth, Yarmouth Port, Chatham, Harwich
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum
Edward Gorey House ©
Edward Gorey House

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.
Change things up with these side-trips from Provincetown: Nauset Beach (in Orleans), Chatham Marconi Maritime Center (in North Chatham) and Chatham Railroad Museum (in Chatham). The adventure continues: pause for some photo ops at Pilgrim Monument & Provincetown Museum, tour the pleasant surroundings at Long Point, take in the waterfront at MacMillan Wharf, and kick back and relax at Cape Cod National Seashore.

To see maps, traveler tips, ratings, and tourist information, go to the Provincetown trip maker app.

You can drive from Sandwich to Provincetown in 1.5 hours. Another option is to take a bus. In August, daytime highs in Provincetown are °C, while nighttime lows are °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, Cape Cod, Chatham, Wellfleet, Truro Vineyards of Cape Cod
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Pilgrim Monument & Provincetown Museum ©
Pilgrim Monument & Provincetown Museum
Cape Cod National Seashore ©
Cape Cod National Seashore

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