31 days in Massachusetts Itinerary

31 days in Massachusetts Itinerary

Created using Inspirock United States trip itinerary planner

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Route & dates

31 days in Massachusetts Itinerary

Start: Boston
Boston
— 5 nights
ferry:  1​h 30​min
Provincetown
— 3 nights
taxi + ferry:  2​h 15​min
Nantucket
— 5 nights
Fly + bus:  1​h 30​min
Oak Bluffs, Martha's Vineyard
— 5 nights
ferry:  30​min
Falmouth
— 4 nights
Drive:  3​h 15​min
Sturbridge
— 3 nights
Drive:  2​h 30​min
Pittsfield
— 5 nights
Drive:  4​h
End: Boston

5
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.
Discover out-of-the-way places like Harvard University and New England Holocaust Memorial. Explore Boston's surroundings by going to Salem (The House of the Seven Gables & Peabody Essex Museum). There's still lots to do: admire the masterpieces at Isabella Stewart Gardner Museum, enjoy breathtaking views from Prudential Center, go for a walk through Quincy Market, and take a stroll through Beacon Hill.

For more things to do, maps, and tourist information, you can read our Boston itinerary maker .

Use the Route module to find suitable travel options from your home destination to Boston. Expect a daytime high around 38°F in January, and nighttime lows around 24°F. Finish up your sightseeing early on the 6th (Sat) so you can catch the ferry to Provincetown.

Things to do in Boston

#Museums, #Shopping, #Neighborhoods

Side Trips

Cambridge, Salem
Highlights from your plan
Isabella Stewart Gardner Museum ©
Isabella Stewart Gardner Museum
Harvard University ©
Harvard University
Beacon Hill ©
Beacon Hill

3
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 hidden gems such as Race Point Beach and Atwood House & Museum. Explore the numerous day-trip ideas around Provincetown: Church of the Transfiguration (in Orleans) and Chatham (The East Wind Silver Co., Ltd, Chatham's Godfrey Windmill, & more). Spend the 7th (Sun) observing fascinating marine mammals with a dolphin and whale watching tour. There's much more to do: see the interesting displays at Pilgrim Monument & Provincetown Museum, enjoy the sea views from Wood End Lighthouse, get lost in a book at Wellfleet Library, and take in the exciting artwork at Rice Polak Gallery.

To see other places to visit, photos, and other tourist information, use the Provincetown driving holiday planner.

Traveling by ferry from Boston to Provincetown takes 1.5 hours. Alternatively, you can do a combination of bus and flight; or drive. In January, daytime highs in Provincetown are 39°F, while nighttime lows are 28°F. Wrap up your sightseeing on the 9th (Tue) to allow time to travel to Nantucket.

Things to do in Provincetown

#Outdoors, #Tours, #Wildlife

Side Trips

Chatham, Wellfleet Public Library, Church of the Transfiguration
Highlights from your plan
Race Point Beach ©
Race Point Beach
Dolphin & Whale Watching
Spas & Wellness

5
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. You'll discover tucked-away gems like Whaling Museum and Nantucket Atheneum. And it doesn't end there: get great views at First Congregational Church, contemplate the long history of Greater Light, don't miss a visit to Old Mill, and tour the pleasant surroundings at Cisco Beach.

For other places to visit, photos, reviews, and tourist information, read our Nantucket travel route planner .

You can do a combination of taxi and ferry from Provincetown to Nantucket in 2.5 hours. Another option is to do a combination of bus and ferry. In January in Nantucket, expect temperatures between 38°F during the day and 26°F at night. Wrap up your sightseeing on the 14th (Sun) early enough to ride a ferry to Oak Bluffs.

Things to do in Nantucket

#Historic Sites, #Parks, #Outdoors
Highlights from your plan
First Congregational Church ©
First Congregational Church
Whaling Museum ©
Whaling Museum
Greater Light ©
Greater Light

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. Step off the beaten path and head to Oak Bluffs Public Library and Farm Neck Golf Club. Venture out of the city with trips to Gay Head (in Aquinnah), Mytoi (in Edgartown) and Chilmark (Menemsha Hills & Chilmark Chocolates). There's much more to do: get outside with My Brother Charters, steep yourself in history at Trinity Park Tabernacle, stop by Ben and Bill's Chocolate Emporium, and examine the collection at Cottage Museum.

To see photos, other places to visit, maps, and other tourist information, read our Oak Bluffs driving holiday planner.

Getting from Nantucket to Oak Bluffs by ferry takes about 1.5 hours. Other options: do a combination of ferry and taxi. In January, daily temperatures in Oak Bluffs can reach 38°F, while at night they dip to 23°F. Wrap up your sightseeing on the 19th (Fri) to allow time to ride a ferry to Falmouth.

Things to do in Oak Bluffs

#Outdoors, #Parks, #Golf

Side Trips

Edgartown, Chilmark, Black Dog Bakery, Polly Hill Arboretum, Gay Head
Highlights from your plan
Farm Neck Golf Club ©
Farm Neck Golf Club
Edgartown Public Library ©
Edgartown Public Library
Polly Hill Arboretum ©
Polly Hill Arboretum

4
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. You'll discover tucked-away gems like Plimoth Plantation and Hart Farm. Get out of town with these interesting Falmouth side-trips: Mayflower II (in Plymouth), New Bedford (New Bedford Whaling Museum, St Anthony of Padua Parish, & more) and Sandwich (Heritage Museums & Gardens & Dexter Grist Mill). There's still lots to do: stroll through Shining Sea Bikeway, visit a coastal fixture at Nobska Point Lighthouse, play a few rounds at Cape Cod Country Club, and experience rural life at Coonamessett Farm.

To find traveler tips, other places to visit, reviews, and more tourist information, you can read our Falmouth online day trip planner .

Falmouth is very close to Oak Bluffs. In January, plan for daily highs up to 38°F, and evening lows to 22°F. Wrap up your sightseeing by early afternoon on the 23rd (Tue) to allow enough time to travel to Sturbridge.

Things to do in Falmouth

#Museums, #Historic Sites, #Outdoors

Side Trips

Sandwich, New Bedford, Plymouth, Cahoon Museum of American Art, Unitarian Memorial Church
Highlights from your plan
Plimoth Plantation ©
Plimoth Plantation
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Hart Farm Nursery ©
Hart Farm Nursery

3
nights
Sturbridge

Sturbridge ©
Sturbridge is a town in Worcester County, Massachusetts, United States. Eschew the tourist crowds and head to Old Sturbridge Village and Wachusett Mountain Ski Area. Explore the numerous day-trip ideas around Sturbridge: Mount Tom State Reservation (in Holyoke), Dr. Seuss National Memorial Sculpture Garden (in Springfield) and McCray's Farm (in South Hadley). There's still lots to do: admire the masterpieces at Worcester Art Museum.

To find maps, more things to do, other places to visit, and more tourist information, go to the Sturbridge trip planner .

Traveling by car from Falmouth to Sturbridge takes 2 hours. Plan for a bit cooler temperatures traveling from Falmouth in January, with highs in Sturbridge at 31°F and lows at 17°F. Finish your sightseeing early on the 26th (Fri) to allow enough time to travel to Pittsfield.

Things to do in Sturbridge

#Parks, #Nature, #Outdoors

Side Trips

Wachusett Mountain Ski Area, Mount Tom State Reservation, McCray's Farm, Dr. Seuss National Memorial Sculpture Garden, Worcester Art Museum
Highlights from your plan
Mount Tom State Reservation ©
Mount Tom State Reservation
Old Sturbridge Village ©
Old Sturbridge Village
Worcester Art Museum ©
Worcester Art Museum

5
nights
Pittsfield

Pittsfield ©
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Explore hidden gems such as Clark Art Institute and Jiminy Peak Mountain Resort. Change things up with these side-trips from Pittsfield: Williamstown (Sweet Brook Farm & Williams College), Les Trois Emme Vineyard & Winery (in New Marlborough) and Ski Butternut (in Great Barrington). There's much more to do: explore the world behind art at MASS MoCA, view the masterpieces at Schantz Galleries, look for gifts at Guido's Fresh Marketplace, and experience rural life at Hancock Shaker Village.

Make your Pittsfield itinerary with Inspirock to find out what to see and where to go.

Traveling by car from Sturbridge to Pittsfield takes 1.5 hours. Expect a daytime high around 29°F in January, and nighttime lows around 13°F. Wrap up your sightseeing on the 31st (Wed) early enough to travel back home.

Things to do in Pittsfield

#Parks, #Outdoors, #Winter Sports

Side Trips

Williamstown, Jiminy Peak Mountain Resort, MASS MoCA, Ski Butternut, A.L. Avery & Son General Store
Highlights from your plan
Jiminy Peak Mountain Resort ©
Jiminy Peak Mountain Resort
The Clark Art Institute ©
The Clark Art Institute
MASS MoCA ©
MASS MoCA

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