22 days in Massachusetts Itinerary

Created using Klarna Trips Massachusetts journey planner
Make it your trip
Train to Amsterdam Schiphol, Fly to Boston
1
Boston
— 5 nights
Fly
2
Oak Bluffs, Martha's Vineyard
— 2 nights
Ferry
3
Nantucket
— 4 nights
Ferry
4
Hyannis
— 5 nights
Drive
5
Provincetown
— 5 nights
+2
Ferry to World Trade Center Pier, Boston, MA, Fly to Amsterdam Schiphol, Train to Brussels

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Boston — 5 nights

Beantown

Get some cultural insight at Freedom Trail and Museum of Fine Arts. Deepen your sense of the past at sights like The House of the Seven Gables and Louisa May Alcott's Orchard House. Explore Boston's surroundings by going to Dolphin & Whale Watching (in Gloucester), Salem Witch Museum (in Salem) and Independence Park (in Beverly). There's lots more to do: get engrossed in the history at John F. Kennedy Presidential Museum & Library, contemplate in the serene atmosphere at Trinity Church, take a stroll through North End, and contemplate the long history of The Paul Revere House.

To see other places to visit, where to stay, ratings, and more tourist information, refer to the Boston attractions planning app.

Brussels, Belgium to Boston is an approximately 11.5-hour combination of train and flight. Due to the time zone difference, you'll gain 6 hours traveling from Brussels to Boston. Traveling from Brussels in September, things will get a bit warmer in Boston: highs are around 28°C and lows about 17°C. Finish your sightseeing early on the 9th (Sat) so you can fly to Oak Bluffs.
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Side Trips
Find places to stay Sep 4 — 9:

Oak Bluffs, Martha's Vineyard — 2 nights

On the 10th (Sun), pause for some serene contemplation at Old Whaling Church, then enjoy the sea views from Edgartown Lighthouse, then kick back and relax at Katama Beach/ South Beach, and finally enjoy the sand and surf at Norton Point Beach. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Menemsha Public Beach, then tour the pleasant surroundings at Menemsha Hills, and then contemplate the long history of Trinity Park Tabernacle.

To see where to stay, ratings, more things to do, and more tourist information, refer to the Oak Bluffs holiday tool.

Fly from Boston to Oak Bluffs in 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. Plan for little chillier nights when traveling from Boston in September since evenings lows in Oak Bluffs dip to 14°C. Cap off your sightseeing on the 11th (Mon) early enough to catch the ferry to Nantucket.
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Beaches · Outdoors · Parks · Historic Sites
Side Trips
Find places to stay Sep 9 — 11:

Nantucket — 4 nights

You'll enjoy a bit of beach vacationing at Jetties Beach and Siasconset Beach. Your cultural itinerary includes sights like Whaling Museum and Sankaty Head Lighthouse.

To see traveler tips, other places to visit, reviews, and more tourist information, you can read our Nantucket journey planning website.

Ride a ferry from Oak Bluffs to Nantucket in 2 hours. In September, plan for daily highs up to 25°C, and evening lows to 17°C. Wrap up your sightseeing on the 15th (Fri) to allow time to ride a ferry to Hyannis.
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Parks · Historic Sites · Beaches · Outdoors
Find places to stay Sep 11 — 15:

Hyannis — 5 nights

Capital of Cape Cod

We've included these beaches for you: Nauset Beach and Corporation Beach. You'll explore and learn at Heritage Museums & Gardens and Edward Gorey House. Venture out of the city with trips to Falmouth (Highfield Hall & Gardens & Old Silver Beach), Chatham (Chatham Lighthouse Beach & Atwood Museum) and Plymouth (Mayflower II, Plymouth Rock, &more). Next up on the itinerary: stroll through Craigville Beach, enjoy the sand and surf at Gray's Beach, see the interesting displays at John F Kennedy Hyannis Museum, and steep yourself in history at Marconi-RCA Wireless Museum.

To see where to stay, other places to visit, photos, and other tourist information, read our Hyannis route builder website.

Traveling by ferry from Nantucket to Hyannis takes 2 hours. Alternatively, you can fly. In September, daily temperatures in Hyannis can reach 26°C, while at night they dip to 16°C. Wrap up your sightseeing on the 20th (Wed) to allow time to drive to Provincetown.
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Parks · Museums · Beaches · Outdoors
Side Trips
Find places to stay Sep 15 — 20:

Provincetown — 5 nights

Birthplace of American Liberty

Museum-lovers will appreciate Pilgrim Monument & Provincetown Museum and Salt Pond Visitor Center. Your itinerary includes some good beach time at Race Point Beach and Coast Guard Beach. Explore Provincetown's surroundings by going to Eastham (Nauset Light Beach & Captain Penniman House). Spend the 22nd (Fri) exploring nature at Cape Cod National Seashore. There's lots more to do: enjoy the sand and surf at Long Point, snap pictures at Uncle Tim's Bridge, and tour the pleasant surroundings at Corn Hill Beach.

For maps, other places to visit, where to stay, and other tourist information, refer to the Provincetown trip planner.

Traveling by car from Hyannis to Provincetown takes 1.5 hours. Alternatively, you can drive; or take a bus. September in Provincetown sees daily highs of 25°C and lows of 16°C at night. Finish your sightseeing early on the 25th (Mon) to allow enough time to travel back home.
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Beaches · Outdoors · Parks · Nature
Side Trips
Find places to stay Sep 20 — 25:

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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