18 days in Massachusetts Itinerary

18 days in Massachusetts Itinerary

Created using Inspirock Massachusetts sightseeing planner

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Route & dates

18 days in Massachusetts Itinerary

Start: New York City
bus + Fly:  3​h
1
Boston
— 5 nights
ferry:  1​h 30​min
2
Provincetown
— 3 nights
Drive:  1​h 15​min
3
Sandwich
— 3 nights
Drive:  2​h 45​min
4
Nantucket
— 3 nights
ferry + Drive:  3​h
5
Salem
— 3 nights
Drive:  4​h 15​min
End: New York City

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.
You've now added Isabella Stewart Gardner Museum to your itinerary. Get out of town with these interesting Boston side-trips: Marginal Way Walkway (in Ogunquit) and The House of the Seven Gables (in Salem). There's still lots to do: admire the masterpieces at Museum of Fine Arts, take an in-depth tour of John F. Kennedy Presidential Museum & Library, get to know the fascinating history of Freedom Trail, and walk around Boston Public Garden.

To see photos, reviews, more things to do, and more tourist information, you can read our Boston online trip itinerary builder .

New York City to Boston is an approximately 3-hour combination of bus and flight. You can also fly; or drive. Prepare for a bit cooler weather when traveling from New York City in October: high temperatures in Boston hover around 64°F and lows are around 50°F. Wrap up your sightseeing on the 15th (Thu) to allow time to ride a ferry to Provincetown.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Marginal Way Walkway, The House of the Seven Gables, Nubble Lighthouse
Highlights from your plan
Isabella Stewart Gardner Museum ©
Isabella Stewart Gardner Museum
Museum of Fine Arts ©
Museum of Fine Arts
Marginal Way Walkway ©
Marginal Way Walkway

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 the numerous day-trip ideas around Provincetown: Salt Pond Visitor Center (in Eastham) and Nauset Beach (in Orleans). There's still lots to do: appreciate the history behind Pilgrim Monument & Provincetown Museum, make a trip to Commercial Street, take a leisurely stroll along MacMillan Wharf, and get lost in a book at Provincetown Library.

For maps, other places to visit, ratings, and other tourist information, you can read our Provincetown trip tool .

Traveling by ferry from Boston to Provincetown takes 1.5 hours. Alternatively, you can fly; or drive. In October, daily temperatures in Provincetown can reach 63°F, while at night they dip to 49°F. Cap off your sightseeing on the 18th (Sun) early enough to go by car to Sandwich.

Things to do in Provincetown

Parks Beaches Outdoors

Side Trips

Salt Pond Visitor Center, Uncle Tim's Bridge, Nauset Beach
Highlights from your plan
Race Point Beach ©
Race Point Beach
Pilgrim Monument & Provincetown Museum ©
Herring Cove Beach ©
Herring Cove Beach

3
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Venture out of the city with trips to Newport (The Breakers, Ocean Drive Historic District, & more). The adventure continues: see the interesting displays at Heritage Museums & Gardens, take an in-depth tour of Plimoth Plantation, steep yourself in history at Hoxie House, and don't miss a visit to Mayflower II.

For traveler tips, ratings, where to stay, and other tourist information, read Sandwich attractions planning app .

Drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. October in Sandwich sees daily highs of 64°F and lows of 46°F at night. Wrap up your sightseeing on the 21st (Wed) early enough to drive to Nantucket.

Things to do in Sandwich

Museums Historic Sites Outdoors

Side Trips

Newport, Plymouth
Highlights from your plan
The Breakers ©
The Breakers
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation

3
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, sample the fine beverages at Cisco Brewers, get engrossed in the history at Egan Maritime's Nantucket Shipwreck & Lifesaving Museum, and visit a coastal fixture at Great Point Light.

To find other places to visit, where to stay, reviews, and more tourist information, use the Nantucket online trip planner .

You can drive from Sandwich to Nantucket in 3 hours. October in Nantucket sees daily highs of 64°F and lows of 51°F at night. Cap off your sightseeing on the 24th (Sat) early enough to travel to Salem.

Things to do in Nantucket

Parks Beaches Outdoors
Highlights from your plan
Madaket Beach ©
Madaket Beach
Whaling Museum ©
Whaling Museum
Great Point Light ©
Great Point Light

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.
Kick off your visit on the 25th (Sun): see the interesting displays at Peabody Essex Museum, get engrossed in the history at Salem Witch Museum, steep yourself in history at The House of the Seven Gables, then view the masterpieces at Fished Impressions, and finally take a leisurely stroll along Pickering Wharf. On the 26th (Mon), you'll have a packed day of sightseeing: walk around Salem Witch Trials Memorial, appreciate the extensive heritage of Marginal Way Walkway, and then enjoy the sea views from Nubble Lighthouse.

To find more things to do, ratings, other places to visit, and more tourist information, use the Salem road trip planning site .

Do a combination of ferry and car from Nantucket to Salem in 3 hours. Alternatively, you can fly; or do a combination of ferry and bus. Traveling from Nantucket in October, you can expect nighttime temperatures to be little chillier in Salem, with lows of 45°F. Wrap up your sightseeing by early afternoon on the 27th (Tue) to allow enough time to drive back home.

Things to do in Salem

Historic Sites Museums Parks

Side Trips

Marginal Way Walkway, Nubble Lighthouse
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
The House of the Seven Gables ©
The House of the Seven Gables
Salem Witch Museum ©
Salem Witch Museum

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