44 days in Massachusetts Itinerary

44 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner

Plan created by another user. Make it yours
Fly
1
Oak Bluffs, Martha's Vineyard
— 3 nights
Ferry
2
Nantucket
— 6 nights
Ferry
3
Hyannis
— 6 nights
Drive
4
Provincetown
— 7 nights
Ferry
5
Boston
— 14 nights
Drive
6
Lenox
— 7 nights
Fly

S M T W T F S
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3
nights
Oak Bluffs, Martha's Vineyard

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Get some cultural insight at Trinity Park Tabernacle and West Chop. There's much more to do: tee off at Farm Neck Golf Club, view the masterpieces at Granary Gallery, contemplate the long history of Vincent House Museum, and wander the streets of Martha's Vineyard Camp meeting Association (MVCMA).

To find maps, other places to visit, where to stay, and tourist information, you can read our Oak Bluffs sightseeing planner.

Detroit to Oak Bluffs is an approximately 7.5-hour flight. You can also do a combination of car and ferry; or do a combination of bus and ferry. In October, daily temperatures in Oak Bluffs can reach 65°F, while at night they dip to 46°F. Wrap up your sightseeing on the 19th (Mon) early enough to ride a ferry to Nantucket.

Things to do in Oak Bluffs

Historic Sites · Parks · Wildlife · Neighborhoods

Side Trips

Highlights from your trip
Trinity Park Tabernacle ©
Architectural Building
Trinity Park Tabernacle
4.7
Edgartown Lighthouse ©
Lighthouse
Edgartown Lighthouse
4.6

6
nights
Nantucket

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Whaling Museum and Oldest House (Jethro Coffin House) and Kitchen Garden are good opportunities to explore the local culture. There's still lots to do: visit a coastal fixture at Great Point Light, make a trip to Brant Point Lighthouse, experience rural life at Moors End Farm, and play a few rounds at Miacomet Golf Club.

Plan trip to Nantucket with our itinerary maker to find out where to go and what to do.

Traveling by ferry from Oak Bluffs to Nantucket takes 2 hours. In October, daytime highs in Nantucket are 64°F, while nighttime lows are 51°F. Finish your sightseeing early on the 25th (Sun) to allow enough time to ride a ferry to Hyannis.

Things to do in Nantucket

Historic Sites · Museums · Outdoors · Parks
Highlights from your trip

6
nights
Hyannis

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Your cultural itinerary includes sights like Sandwich Glass Museum and John F Kennedy Hyannis Museum. Explore the numerous day-trip ideas around Hyannis: Chatham Marconi Maritime Center (in North Chatham), Chatham (Chatham Railroad Museum, Atwood Museum, &more) and Plymouth (The Jenney, Plymouth Rock, &more). Next up on the itinerary: examine the collection at Edward Gorey House, make a trip to Old King's Hwy, admire the masterpieces at Highfield Hall & Gardens, and enjoy the sea views from Nobska Point Lighthouse.

For photos, where to stay, reviews, and tourist information, read Hyannis trip planning tool.

You can ride a ferry from Nantucket to Hyannis in 2 hours. Alternatively, you can fly. October in Hyannis sees daily highs of 64°F and lows of 48°F at night. Cap off your sightseeing on the 31st (Sat) early enough to go by car to Provincetown.

Things to do in Hyannis

Museums · Historic Sites · Outdoors · Parks

Side Trips

Highlights from your trip
Heritage Museums & Gardens ©
Specialty Museum
Heritage Museums & Gardens
4.7
Plimoth Plantation ©
History Museum
Plimoth Plantation
4.2

7
nights
Provincetown

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.
Satisfy your inner culture vulture at Pilgrim Monument & Provincetown Museum and Charles-Baltivik Gallery and Sculpture Garden. Explore Provincetown's surroundings by going to Eastham (Captain Penniman House, Nauset Light Beach, &more). There's lots more to do: enjoy the sand and surf at Cape Cod National Seashore, get a sense of history and politics at Provincetown Town Hall, identify plant and animal life at Art's Dune Tours, and stroll through Cape Cod Provincelands Trail.

Ask Inspirock to suggest an itinerary and make planning a trip to Provincetown fast, fun, and easy.

Drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. In October, daily temperatures in Provincetown can reach 63°F, while at night they dip to 49°F. Finish your sightseeing early on the 7th (Sat) to allow enough time to ride a ferry to Boston.

Things to do in Provincetown

Outdoors · Parks · Museums · Beaches

Side Trips

Highlights from your trip

14
nights
Boston

Beantown

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.
Do some cultural sightseeing at Museum of Fine Arts and John F. Kennedy Presidential Museum & Library. Explore the numerous day-trip ideas around Boston: Lizzie Borden House (in Fall River), Salem (Fished Impressions, Old Burying Point Cemetery, &more) and Concord (Walden Pond State Reservation, Minuteman National Park - Old North Bridge, &more). There's lots more to do: appreciate the extensive heritage of Freedom Trail, walk around Boston Common, explore the world behind art at Isabella Stewart Gardner Museum, and take in the architecture and atmosphere at Trinity Church.

For more things to do, where to stay, other places to visit, and more tourist information, you can read our Boston trip itinerary builder.

Traveling by ferry from Provincetown to Boston takes 2.5 hours. Alternatively, you can fly; or drive. November in Boston sees daily highs of 52°F and lows of 37°F at night. Wrap up your sightseeing on the 21st (Sat) to allow time to drive to Lenox.

Things to do in Boston

Side Trips

Highlights from your trip

7
nights
Lenox

Lenox is an affluent town in Berkshire County, Massachusetts, United States. Satisfy your inner culture vulture at Norman Rockwell Museum and Hancock Shaker Village. Explore the numerous day-trip ideas around Lenox: Chester Railway Station (in Chester), North Adams (MASS MoCA & Sanford Blackinton Mansion, North Adams Public Library) and The Clark Art Institute (in Williamstown). The adventure continues: take an in-depth tour of The Mount, Edith Wharton's Home, stroll around Stanley park, take in the spiritual surroundings of National Shrine of the Divine Mercy, and tour the pleasant surroundings at Ashuwillticook Rail Trail.

To find ratings, photos, reviews, and more tourist information, use the Lenox trip planner.

You can drive from Boston to Lenox in 2.5 hours. Other options are to take a bus; or do a combination of train and bus. Traveling from Boston in November, things will get slightly colder in Lenox: highs are around 47°F and lows about 28°F. Finish your sightseeing early on the 28th (Sat) to allow enough time to travel back home.

Things to do in Lenox

Museums · Historic Sites · Parks · Outdoors

Side Trips

Highlights from your trip
MASS MoCA ©
Art Museum
MASS MoCA
4.6

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