11 days in Massachusetts Itinerary

Created using Klarna Trips Massachusetts sightseeing planner
Make it your trip
Drive
1
Salem
— 2 nights
Drive
2
Boston
— 2 nights
Drive
3
Eastham
— 2 nights
Drive
4
Chatham
— 2 nights
+2
Drive to Woods Hole, Ferry to Martha's Vineyard, Drive to Edgartown
5
Edgartown
— 2 nights
Fly

S M T W T F S
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7

Salem — 2 nights

Witch City

Venture out of the city with trips to Fishermen's Memorial Monument (in Gloucester) and Ipswich Ale Brewery (in Ipswich). Next up on the itinerary: look for all kinds of wild species at Wildlife Areas, walk around Salem Witch Trials Memorial, go for a stroll along the water at Pickering Wharf, and explore the different monuments and memorials at Old Burying Point Cemetery.

To find ratings, more things to do, reviews, and other tourist information, you can read our Salem driving holiday planner.

Boston to Salem is an approximately 1-hour car ride. You can also take a train; or take a bus. Traveling from Boston in September, Salem is slightly colder at night with lows of 14°C. Finish your sightseeing early on the 25th (Mon) to allow enough time to drive to Boston.
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Historic Sites · Museums · Tours · Outdoors
Side Trips
Find places to stay Sep 23 — 25:

Boston — 2 nights

Beantown

On the 26th (Tue), make a trip to Faneuil Hall Marketplace, get to know the fascinating history of Freedom Trail, then visit North End, and finally walk around Boston Common. Get ready for a full day of sightseeing on the 27th (Wed): take an in-depth tour of Boston Tea Party Ships & Museum, admire the masterpieces at Museum of Fine Arts, and then admire the natural beauty at Boston Public Garden.

To find other places to visit, maps, traveler tips, and more tourist information, go to the Boston route planner.

Drive from Salem to Boston in an hour. Alternatively, you can take a train; or take a bus. In September in Boston, expect temperatures between 28°C during the day and 17°C at night. Cap off your sightseeing on the 27th (Wed) early enough to go by car to Eastham.
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Find places to stay Sep 25 — 27:

Eastham — 2 nights

Start off your visit on the 28th (Thu): explore the striking landscape of Cape Cod National Seashore.

To see ratings, traveler tips, and more tourist information, refer to the Eastham online road trip planner.

Getting from Boston to Eastham by car takes about 2 hours. Other options: fly; or take a bus. In September, plan for daily highs up to 26°C, and evening lows to 17°C. Finish up your sightseeing early on the 29th (Fri) so you can go by car to Chatham.
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Outdoors · Nature · Parks · Beaches
Side Trip
Find places to stay Sep 27 — 29:
Highlights from your trip

Chatham — 2 nights

Start off your visit on the 29th (Fri): see the interesting displays at Chatham Railroad Museum, hike along Cape Cod Rail Trail, and then make a trip to Chatham's Godfrey Windmill. Get ready for a full day of sightseeing on the 30th (Sat): take a leisurely stroll along Chatham Pier and Fish Market, kick back and relax at Chatham Lighthouse Beach, then get engrossed in the history at Atwood Museum, and finally get curious at Marconi-RCA Wireless Museum.

To see where to stay, more things to do, maps, and other tourist information, read Chatham journey planner.

Chatham is just a stone's throw from Eastham. In September, daytime highs in Chatham are 26°C, while nighttime lows are 17°C. Finish your sightseeing early on the 1st (Sun) to allow enough time to travel to Edgartown.
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Outdoors · Parks · Trails · Historic Sites
Side Trip
Find places to stay Sep 29 — Oct 1:

Edgartown — 2 nights

Start off your visit on the 1st (Sun): enjoy the sea views from Edgartown Lighthouse, experience rural life at Morning Glory Farm, make a trip to Circuit Avenue, then don't miss a visit to Flying Horses Carousel, and finally stroll around Ocean Park. Get ready for a full day of sightseeing on the next day: take in nature's colorful creations at Mytoi, then admire the landmark architecture of Trinity Park Tabernacle, then take a stroll through Martha's Vineyard Camp meeting Association (MVCMA), and finally enjoy the sand and surf at Katama Beach/ South Beach.

To find traveler tips, more things to do, maps, and more tourist information, read our Edgartown road trip tool.

Traveling by combination of car and ferry from Chatham to Edgartown takes 3 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. Expect a daytime high around 21°C in October, and nighttime lows around 9°C. Finish up your sightseeing early on the 3rd (Tue) so you can catch the flight back home.
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Parks · Historic Sites · Neighborhoods · Outdoors
Side Trip
Find places to stay Oct 1 — 3:

Massachusetts travel guide

4.3
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.
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