8 days in Massachusetts Itinerary

8 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner

Plan created by another user. Make it yours
1
Nantucket
— 1 night
2
Chatham
— 2 nights
3
Stockbridge
— 1 night
4
Boston
— 2 nights

S M T W T F S
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23

1
night
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 17th (Sun): see the interesting displays at Whaling Museum, then stop by Aunt Leah's Fudge, then steep yourself in history at Greater Light, and finally get great views at First Congregational Church. Keep things going the next day: make a trip to Brant Point Lighthouse, appreciate the extensive heritage of Altar Rock, then visit a coastal fixture at Sankaty Head Lighthouse, and finally steep yourself in history at Wauwinet.

To find other places to visit and other tourist information, read Nantucket travel itinerary planner.

San Francisco to Nantucket is an approximately 10-hour flight. You can also do a combination of car and ferry; or do a combination of subway, train, bus, and ferry. The time zone difference when traveling from San Francisco to Nantucket is 3 hours. Traveling from San Francisco in February, expect Nantucket to be colder, temps between 40°F and 28°F. Wrap up your sightseeing on the 18th (Mon) to allow time to travel to Chatham.

Things to do in Nantucket

Historic Sites · Museums · Shopping
Highlights from your trip
©
Specialty Museum
Whaling Museum
4.8

2
nights
Chatham

Chatham ©
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Kick off your visit on the 19th (Tue): look for gifts at Chatham Candy Manor, stop by Yankee Ingenuity, look for gifts at Ducks in the Window, then take in the exciting artwork at Maps of Antiquity, then look for gifts at Stage Stop Candy, and finally stop by Fritz Glass. Get ready for a full day of sightseeing on the 20th (Wed): look for gifts at Handcraft House, explore the different monuments and memorials at Cove Burying Ground, then enjoy the sea views from Chatham Lighthouse, then look for gifts at Pilgrim's Landing, and finally browse for treasures at Yak Arts.

Quickly create a custom-made itinerary for Chatham using our trip planner.

Traveling by combination of ferry and taxi from Nantucket to Chatham takes 2.5 hours. Alternatively, you can do a combination of ferry and bus. Expect a daytime high around 39°F in February, and nighttime lows around 26°F. Finish your sightseeing early on the 20th (Wed) so you can drive to Stockbridge.

Things to do in Chatham

Shopping · Museums · Historic Sites

Side Trips

Highlights from your trip
©
Must see
Maps of Antiquity
4.9
©
Lighthouse
Chatham Lighthouse
4.3
©
Gift & Specialty Shop
Chatham Candy Manor
4.7

1
night
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. On the 21st (Thu), stop by Charles H. Baldwin & Sons, get a taste of the local shopping with Concepts of Art Lenox Judaica, take in the spiritual surroundings of Congregational Church, then take in the exciting artwork at Ozzie's Glass Gallery, then view the masterpieces at Schantz Galleries Contemporary Glass, and finally look for gifts at Williams & Sons Country Store.

For maps, more things to do, ratings, and other tourist information, read our Stockbridge trip site.

You can drive from Chatham to Stockbridge in 4 hours. Other options are to do a combination of taxi, bus, and train; or take a bus. Prepare for little chillier weather when traveling from Chatham in February: high temperatures in Stockbridge hover around 34°F and lows are around 15°F. Cap off your sightseeing on the 21st (Thu) early enough to go by car to Boston.

Things to do in Stockbridge

Shopping · Museums · Historic Sites · Outdoors

Side Trips

Highlights from your trip
©
Religious Site
Congregational Church
4.9
©
Art Gallery
Ozzie's Glass Gallery
4.9

2
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.
On the 22nd (Fri), take a stroll through Newbury Street, then explore the world behind art at Museum of Fine Arts, and then appreciate the extensive heritage of Freedom Trail. Get ready for a full day of sightseeing on the 23rd (Sat): steep yourself in history at The House of the Seven Gables, then take in the architecture and design of Harvard University, then make a trip to Louisburg Square, and finally browse the different shops at Faneuil Hall Marketplace.

To find traveler tips, other places to visit, and other tourist information, read our Boston sightseeing planner.

Getting from Stockbridge to Boston by car takes about 2.5 hours. Other options: take a bus; or take a train. Traveling from Stockbridge in February, Boston is somewhat warmer at night with lows of 24°F. Finish up your sightseeing early on the 23rd (Sat) so you can travel back home.

Things to do in Boston

Side Trips

Highlights from your trip
©
Must see
Freedom Trail
4.7

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