14 days in Massachusetts Itinerary

14 days in Massachusetts Itinerary

Created using Inspirock United States trip itinerary planner

Plan created by another user. Make it yours
1
Boston
— 3 nights
2
Provincetown
— 2 nights
3
Chatham
— 2 nights
4
Sandwich
— 1 night
5
Plymouth
— 2 nights
6
Salem
— 3 nights
7
Stockbridge
— Few hours

S M T W T F S
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3
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.
Get some cultural insight at Newbury Street and Isabella Stewart Gardner Museum. Deepen your sense of the past at sights like Freedom Trail and Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill. Go for a jaunt from Boston to Paxton to see Moore State Park about 1h 20 min away. There's still lots to do: get engrossed in the history at Louisa May Alcott's Orchard House, browse the eclectic array of goods at Quincy Market, take a stroll through North End, and steep yourself in history at The Paul Revere House.

To see where to stay, reviews, maps, and other tourist information, refer to the Boston online road trip planner.

Asheville to Boston is an approximately 7-hour flight. You can also drive; or do a combination of bus and train. When traveling from Asheville in November, plan for slightly colder days and about the same nights in Boston: temperatures range from 52°F by day to 37°F at night. You will have some time to spend on the 4th (Thu) before leaving for Provincetown.

Things to do in Boston

Museums · Historic Sites · Shopping

Side Trips

Moore State Park, Louisa May Alcott's Orchard House
Highlights from your plan
Freedom Trail ©
Freedom Trail
Boston Tea Party Ships & Museum ©
Boston Tea Party Ships & Museum

2
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.
On the 4th (Thu), enjoy the sand and surf at Race Point Beach, take in the waterfront at MacMillan Wharf, and then view the masterpieces at Cortile Gallery. Get ready for a full day of sightseeing on the next day: pause for some photo ops at Pilgrim Monument & Provincetown Museum, shop like a local with Charles-Baltivik Gallery and Sculpture Garden, then stop by Marine Specialties, and finally tour the pleasant surroundings at Cape Cod National Seashore.

To find more things to do, photos, ratings, and other tourist information, read our Provincetown trip planner.

Traveling by ferry from Boston to Provincetown takes 2.5 hours. Alternatively, you can fly; or drive. In November, daily temperatures in Provincetown can reach 51°F, while at night they dip to 39°F. Wrap up your sightseeing by early afternoon on the 6th (Sat) to allow enough time to drive to Chatham.

Things to do in Provincetown

Outdoors · Parks · Beaches

Side Trips

Cape Cod National Seashore, Highland Light
Highlights from your plan
Race Point Beach ©
Race Point Beach
Pilgrim Monument & Provincetown Museum ©
Pilgrim Monument & Provincetown Museum
Cape Cod National Seashore ©
Cape Cod National Seashore

2
nights
Chatham

Chatham ©
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Start off your visit on the 6th (Sat): get engrossed in the history at Chatham Marconi Maritime Center, enjoy the sand and surf at Chatham Lighthouse Beach, and then enjoy the sand and surf at Nauset Beach. Keep things going the next day: shop like a local with Chatham Pier and Fish Market, then visit a coastal fixture at Nauset Lighthouse, and then make a trip to Chatham's Godfrey Windmill.

To see ratings, traveler tips, where to stay, and more tourist information, use the Chatham trip itinerary planning website.

Drive from Provincetown to Chatham in an hour. Alternatively, you can take a bus. In November, daily temperatures in Chatham can reach 52°F, while at night they dip to 39°F. You'll have a few hours on the 8th (Mon) to wrap things up before traveling to Sandwich.

Things to do in Chatham

Outdoors · Parks · Beaches

Side Trips

Eastham, Nauset Beach
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Salt Pond Visitor Center ©
Salt Pond Visitor Center
Nauset Beach ©
Nauset Beach

1
night
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Kick off your visit on the 8th (Mon): take in the exciting artwork at Samuell Day Gallery, steep yourself in history at Hoxie House, then engage your brain at Sandwich Glass Museum, and finally visit a coastal fixture at Nobska Point Lighthouse. Get ready for a full day of sightseeing on the 9th (Tue): view the masterpieces at McDermott Glass Studio, examine the collection at Heritage Museums & Gardens, then examine the collection at John F Kennedy Hyannis Museum, then stroll through Gray's Beach, and finally kick back and relax at Craigville Beach.

To find maps, photos, traveler tips, and other tourist information, read Sandwich travel route planner.

Traveling by car from Chatham to Sandwich takes an hour. Alternatively, you can take a bus. In November, daytime highs in Sandwich are 53°F, while nighttime lows are 35°F. Wrap up your sightseeing on the 9th (Tue) early enough to drive to Plymouth.

Things to do in Sandwich

Museums · Outdoors · Parks

Side Trips

Nobska Point Lighthouse, Gray's Beach, Samuell Day Gallery, John F Kennedy Hyannis Museum, Craigville Beach
Highlights from your plan
Sandwich Glass Museum ©
Sandwich Glass Museum
Heritage Museums & Gardens ©
Heritage Museums & Gardens
John F Kennedy Hyannis Museum ©
John F Kennedy Hyannis Museum

2
nights
Plymouth

Plymouth ©
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
On the 10th (Wed), don't miss a visit to Plymouth Rock, make a trip to Mayflower II, get engrossed in the history at The Jenney, then take an in-depth tour of Plimoth Plantation, then appreciate the history behind National Monument to the Forefathers, and finally get some fabulous bargains at Wrentham Village Premium Outlets.

To see traveler tips, reviews, where to stay, and other tourist information, refer to the Plymouth trip planner.

Plymouth is very close to Sandwich. In November in Plymouth, expect temperatures between 52°F during the day and 34°F at night. Wrap up your sightseeing by early afternoon on the 11th (Thu) to allow enough time to drive to Salem.

Things to do in Plymouth

Museums · Historic Sites · Shopping

Side Trips

Wrentham Village Premium Outlets, Lizzie Borden House
Highlights from your plan
Mayflower II ©
Mayflower II
Plimoth Plantation ©
Plimoth Plantation
Lizzie Borden House
Lizzie Borden House

3
nights
Salem

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Your day by day itinerary now includes Hex: Old World Witchery, Emporium 32, Enchanted, and other attractions you added. You'll explore and learn at The House of the Seven Gables and Peabody Essex Museum. Salem Witch Museum and Fished Impressions are good opportunities to explore the local culture.

Plan trip to Salem with our itinerary maker to find out where to go and what to do.

Traveling by car from Plymouth to Salem takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In November in Salem, expect temperatures between 51°F during the day and 33°F at night. Finish your sightseeing early on the 14th (Sun) to allow enough time to drive to Stockbridge.

Things to do in Salem

Shopping · Museums · Historic Sites
Highlights from your plan
Crow Haven Corner ©
Crow Haven Corner
The House of the Seven Gables ©
The House of the Seven Gables
Peabody Essex Museum ©
Peabody Essex Museum

few
hours
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. On the 14th (Sun), explore the world behind art at Norman Rockwell Museum and then shop like a local with Schantz Galleries Contemporary Glass.

To find traveler tips, where to stay, more things to do, and more tourist information, refer to the Stockbridge online trip planner.

Drive from Salem to Stockbridge in 3 hours. Alternatively, you can take a bus; or take a train. Traveling from Salem in November, expect little chillier with lows of 28°F in Stockbridge. Finish your sightseeing early on the 14th (Sun) so you can travel back home.

Things to do in Stockbridge

Museums · Shopping
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Schantz Galleries Contemporary Glass ©
Schantz Galleries Contemporary Glass

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