27 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner
Make it your trip
Fly to Boston, Ferry to Provincetown
1
Provincetown
— 4 nights
Drive
2
Hyannis
— 6 nights
Ferry
3
Nantucket
— 4 nights
Ferry
4
Oak Bluffs, Martha's Vineyard
— 4 nights
Fly
5
Boston
— 8 nights
Fly

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Provincetown — 4 nights

Birthplace of American Liberty

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.
Venture out of the city with trips to Eastham (Nauset Light Beach, Coast Guard Beach, &more). Spend the 5th (Sat) exploring nature at Cape Cod National Seashore. The adventure continues: appreciate the history behind Pilgrim Monument & Provincetown Museum, explore the world behind art at Provincetown Art Association and Museum, enjoy the sand and surf at Corn Hill Beach, and tour the pleasant surroundings at Herring Cove Beach.

To see ratings, other places to visit, photos, and tourist information, refer to the Provincetown road trip planning site.

Barcelona, Spain to Provincetown is an approximately 12.5-hour combination of flight and ferry. Traveling from Barcelona to Provincetown, you'll gain 6 hours due to the time zone difference. Traveling from Barcelona in August, things will get a bit cooler in Provincetown: highs are around 30°C and lows about 19°C. Finish your sightseeing early on the 8th (Tue) so you can drive to Hyannis.
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Outdoors · Parks · Beaches · Nature
Side Trips

Hyannis — 6 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Explore the numerous day-trip ideas around Hyannis: Falmouth (Old Silver Beach, Highfield Hall & Gardens, &more), Plymouth (Plimoth Patuxet Museums & Plymouth Rock) and Chatham (Chatham Lighthouse Beach & Atwood Museum). Next up on the itinerary: head outdoors with Hyannis Whale Watcher Cruises, kick back and relax at Nauset Beach, browse the exhibits of Marconi-RCA Wireless Museum, and immerse yourself in nature at Nickerson State Park.

For photos, reviews, ratings, and other tourist information, read Hyannis route planner.

Getting from Provincetown to Hyannis by car takes about 1.5 hours. Other options: take a bus. In August, daily temperatures in Hyannis can reach 30°C, while at night they dip to 20°C. Cap off your sightseeing on the 14th (Mon) early enough to catch the ferry to Nantucket.
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Outdoors · Parks · Museums · Beaches
Side Trips

Nantucket — 4 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, and historic sites. Your trip includes some of its best attractions: visit a coastal fixture at Great Point Light, kick back and relax at Cisco Beach, get engrossed in the history at Nantucket Shipwreck & Lifesaving Museum, and cast your line with a fishing tour.

For more things to do, other places to visit, ratings, and other tourist information, read Nantucket trip planner.

Ride a ferry from Hyannis to Nantucket in 2 hours. Alternatively, you can fly. Expect a daytime high around 28°C in August, and nighttime lows around 20°C. Cap off your sightseeing on the 18th (Fri) early enough to catch the ferry to Oak Bluffs.
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Outdoors · Parks · Beaches · Museums

Oak Bluffs, Martha's Vineyard — 4 nights

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Oak Bluffs is known for sightseeing, beaches, and outdoors. Your trip includes some of its best attractions: admire the striking features of Trinity Park Tabernacle, take in the architecture and atmosphere at Old Whaling Church, visit a coastal fixture at Edgartown Lighthouse, and don't miss a visit to Flying Horses Carousel.

To find more things to do, other places to visit, reviews, and other tourist information, refer to the Oak Bluffs travel itinerary planner.

You can ride a ferry from Nantucket to Oak Bluffs in 2 hours. Expect a daytime high around 30°C in August, and nighttime lows around 17°C. Finish your sightseeing early on the 22nd (Tue) to allow enough time to fly to Boston.
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Outdoors · Parks · Beaches · Historic Sites
Side Trips

Boston — 8 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year.
You'll find plenty of places to visit near Boston: Gloucester (Cape Ann Museum & Dolphin & Whale Watching), Ipswich Ale Brewery (in Ipswich) and Salem (Salem Witch Museum, The House of the Seven Gables, &more). And it doesn't end there: admire the natural beauty at Boston Public Garden, get engrossed in the history at John F. Kennedy Presidential Museum & Library, stop by North End, and stroll around Boston Common.

To see other places to visit, reviews, ratings, and tourist information, go to the Boston trip itinerary planner.

Getting from Oak Bluffs to Boston by flight takes about 2.5 hours. Other options: do a combination of ferry and car; or do a combination of ferry and bus. Plan for somewhat warmer nights when traveling from Oak Bluffs in August since evenings lows in Boston dip to 21°C. Cap off your sightseeing on the 30th (Wed) early enough to catch the flight back home.
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Museums · Parks · Tours · Historic Sites
Side Trips

Massachusetts travel guide

4.3
History Museums · Nightlife · Art Museums
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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