49 days in Massachusetts Itinerary

49 days in Massachusetts Itinerary

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

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Provincetown — 6 nights

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.
Change things up with these side-trips from Provincetown: Eastham (Captain Penniman House, Nauset Light Beach, &more). There's lots more to do: explore the wealth of natural beauty at Cape Cod National Seashore, admire the masterpieces at Provincetown Art Association and Museum, surround yourself with nature on Art's Dune Tours, and appreciate the history behind Pilgrim Monument & Provincetown Museum.

For more things to do, reviews, other places to visit, and tourist information, use the Provincetown trip builder.

Manchester, UK to Provincetown is an approximately 12-hour combination of flight and ferry. The time zone difference moving from Greenwich Mean Time to Eastern Standard Time is minus 5 hours. In October, plan for daily highs up to 20°C, and evening lows to 11°C. Finish your sightseeing early on the 30th (Sun) so you can drive to Hyannis.
Outdoors · Parks · Beaches · Museums
Side Trips

Hyannis — 8 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Venture out of the city with trips to Chatham (Atwood Museum & Chatham Lighthouse Beach), Falmouth (Spohr Gardens, Shining Sea Bikeway, &more) and Plymouth (Plimoth Patuxet, Plymouth Rock, &more). Next up on the itinerary: engage your brain at Sandwich Glass Museum, get up close to creatures of the deep with Hyannis Whale Watcher Cruises, examine the collection at Heritage Museums & Gardens, and tour the pleasant surroundings at Nauset Beach.

For where to stay, more things to do, photos, and tourist information, use the Hyannis trip planner.

Drive from Provincetown to Hyannis in 1.5 hours. Alternatively, you can take a bus. October in Hyannis sees daily highs of 20°C and lows of 10°C at night. Finish up your sightseeing early on the 7th (Mon) so you can catch the ferry to Nantucket.
Museums · Outdoors · Historic Sites · Parks
Side Trips

Nantucket — 7 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: see the interesting displays at Whaling Museum, appreciate the extensive heritage of Milestone Bog, take an in-depth tour of Nantucket Shipwreck & Lifesaving Museum, and enjoy the sea views from Great Point Light.

For traveler tips, where to stay, and tourist information, you can read our Nantucket holiday app.

You can ride a ferry from Hyannis to Nantucket in 2 hours. Another option is to fly. In November, plan for daily highs up to 13°C, and evening lows to 5°C. Cap off your sightseeing on the 14th (Mon) early enough to catch the ferry to Oak Bluffs.
Historic Sites · Parks · Outdoors · Museums

Oak Bluffs, Martha's Vineyard — 5 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 landmark architecture of Trinity Park Tabernacle, take a stroll through Martha's Vineyard Camp meeting Association (MVCMA), admire the natural beauty at Mytoi, and play a few rounds at Farm Neck Golf Club.

For reviews, maps, ratings, and tourist information, use the Oak Bluffs day trip tool.

Getting from Nantucket to Oak Bluffs by ferry takes about 2 hours. Expect a daytime high around 13°C in November, and nighttime lows around 3°C. Finish your sightseeing early on the 19th (Sat) to allow enough time to travel to Lenox.
Parks · Historic Sites · Neighborhoods · Spas
Side Trips

Lenox — 7 nights

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Get out of town with these interesting Lenox side-trips: Clarkdale Fruit Farms (in Deerfield), Adams (Mount Greylock & Ashuwillticook Rail Trail) and Apex Orchards (in Shelburne Falls). Next up on the itinerary: explore the world behind art at Norman Rockwell Museum, view the masterpieces at Schantz Galleries Contemporary Glass, take in the awesome beauty at Monument Mountain, and examine the collection at Polish Center of Discovery and Learning.

To find maps, more things to do, where to stay, and more tourist information, you can read our Lenox holiday planner.

You can do a combination of ferry and car from Oak Bluffs to Lenox in 5 hours. Alternatively, you can do a combination of ferry and bus; or do a combination of ferry, bus, and train. Traveling from Oak Bluffs in November, expect Lenox to be slightly colder, temps between 9°C and -2°C. Cap off your sightseeing on the 26th (Sat) early enough to go by car to Boston.
Museums · Parks · Outdoors · Nature
Side Trips

Boston — 15 nights

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'll find plenty of places to visit near Boston: Concord (The Old North Bridge, Louisa May Alcott's Orchard House, &more) and Salem (Old Burying Point Cemetery, Salem Witch Museum, &more). Next up on the itinerary: admire the natural beauty at Boston Public Garden, explore the world behind art at Museum of Fine Arts, take an in-depth tour of John F. Kennedy Presidential Museum & Library, and browse the different shops at Faneuil Hall Marketplace.

To see more things to do, maps, and tourist information, use the Boston online travel route planner.

Getting from Lenox to Boston by car takes about 2.5 hours. Other options: take a bus; or do a combination of bus and train. Plan for a bit warmer nights when traveling from Lenox in November since evenings lows in Boston dip to 3°C. Finish your sightseeing early on the 11th (Sun) so you can fly back home.
Museums · Historic Sites · Parks · Shopping
Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
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.