29 days in Massachusetts Itinerary

29 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip planner
©
Make it your trip
Fly to Logan International Airport, Drive to Gloucester
1
Gloucester
— 3 nights
Drive
2
Lenox
— 4 nights
Drive
3
Sandwich
— 5 nights
Taxi to 227 Clinton St., Falmouth, MA, Ferry to Oak Bluffs
4
Oak Bluffs, Martha's Vineyard
— 4 nights
Ferry
5
Nantucket
— 6 nights
Ferry to Hyannis, MA, Taxi to Provincetown
6
Provincetown
— 6 nights
Fly

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Gloucester — 3 nights

The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
Step off the beaten path and head to Hammond Castle Museum and The Old North Bridge. Take a break from the city and head to Halibut Point State Park and Crane Beach. Venture out of the city with trips to Louisa May Alcott's Orchard House (in Concord) and Salem Maritime National Historic Site (in Salem). There's lots more to do: kick back and relax at Wingaersheek Beach, pause for some photo ops at Fishermen's Memorial Monument, stroll through Good Harbor Beach, and see what you can catch with a fishing tour.

To find traveler tips, more things to do, other places to visit, and other tourist information, refer to the Gloucester route maker app.

Paris, France to Gloucester is an approximately 14.5-hour combination of flight and car. You can also fly. Traveling from Paris to Gloucester, you'll gain 6 hours due to the time zone difference. In July in Gloucester, expect temperatures between 32°C during the day and 20°C at night. Finish up your sightseeing early on the 14th (Thu) so you can go by car to Lenox.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips

Lenox — 4 nights

Lenox is an affluent town in Berkshire County, Massachusetts, United States. The Mount, Edith Wharton's Home and Yankee Candle Flagship Store will appeal to museum buffs. You'll discover tucked-away gems like MASS MoCA and Hancock Shaker Village. You'll find plenty of places to visit near Lenox: Williams College Museum of Art (in Williamstown), Historic Deerfield (in Deerfield) and Mount Greylock State Reservation (in Lanesborough). There's still lots to do: trek along Herman Melville's Arrowhead, contemplate the long history of Chesterwood Museum, and view the masterpieces at Tom Fiorini Sculpture Yard.

To find more things to do, maps, photos, and more tourist information, read Lenox journey planner.

You can drive from Gloucester to Lenox in 3 hours. Other options are to do a combination of train and bus; or do a combination of train and bus. Traveling from Gloucester in July, expect a bit cooler with lows of 17°C in Lenox. Finish up your sightseeing early on the 18th (Mon) so you can go by car to Sandwich.
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Museums · Historic Sites · Parks · Shopping
Side Trips

Sandwich — 5 nights

Sandwich is a town in Barnstable County, Massachusetts, United States. Take a break from the city and head to Shining Sea Bikeway and National Monument to the Forefathers. Deepen your sense of the past at sights like Nobska Point Lighthouse and Hoxie House. Explore the numerous day-trip ideas around Sandwich: Kalmus Beach (in Hyannis), Seagull Beach (in West Yarmouth) and New Bedford Whaling Museum (in New Bedford). There's still lots to do: explore the world behind art at Sandwich Glass Museum, take a tour by water with Boat Tours & Water Sports, tour the pleasant surroundings at Craigville Beach, and take an in-depth tour of The Jenney.

Discover how to plan a Sandwich trip in just a few steps with Inspirock's itinerary builder.

You can drive from Lenox to Sandwich in 3.5 hours. Other options are to take a bus; or do a combination of bus and train. In July, plan for daily highs up to 31°C, and evening lows to 20°C. Finish up your sightseeing early on the 23rd (Sat) so you can travel to Oak Bluffs.
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Outdoors · Parks · Museums · Beaches
Side Trips

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. Visiting Aquinnah Cliffs and Katama Beach/ South Beach will get you outdoors. Relax by the water at Menemsha Public Beach and Inkwell Beach. Go for a jaunt from Oak Bluffs to Aquinnah to see Gay Head Lighthouse about 38 minutes away. There's still lots to do: get a new perspective on things with Boat Tours & Water Sports, enjoy the sea views from Edgartown Lighthouse, relax in the rural setting at Island Alpaca Company of Martha's Vineyard, and don't miss a visit to Flying Horses Carousel.

For reviews, traveler tips, ratings, and more tourist information, refer to the Oak Bluffs attractions planner.

Traveling by combination of taxi and ferry from Sandwich to Oak Bluffs takes 1.5 hours. Alternatively, you can do a combination of bus and ferry. In July, daytime highs in Oak Bluffs are 30°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 27th (Wed) early enough to ride a ferry to Nantucket.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips

Nantucket — 6 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Satisfy your inner culture vulture at Cisco Brewers and Brant Point Lighthouse. Let the collections at Nantucket Shipwreck & Lifesaving Museum and Nantucket Lightship Basket Museum capture your imagination. There's much more to do: kick back and relax at Cisco Beach, cast your line with a fishing tour, enjoy the sea views from Great Point Light, and don't miss a visit to Old Mill.

Plan my trip to Nantucket with suggested itineraries provided by Inspirock.

Ride a ferry from Oak Bluffs to Nantucket in 2 hours. In July in Nantucket, expect temperatures between 28°C during the day and 20°C at night. Finish your sightseeing early on the 2nd (Tue) so you can travel to Provincetown.
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Outdoors · Parks · Beaches · Historic Sites

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.
Salt Pond Visitor Center and Provincetown Town Hall will appeal to museum buffs. Escape the urban bustle at Art's Dune Tours and Wellfleet Bay Wildlife Sanctuary. Change things up with these side-trips from Provincetown: Eastham (First Encounter Beach, Coast Guard Beach, &more). Next up on the itinerary: kick back and relax at Marconi Beach, admire the masterpieces at Provincetown Art Association and Museum, stroll through Head of the Meadow Beach, and enjoy the sea views from Highland Light.

For ratings, other places to visit, where to stay, and tourist information, use the Provincetown road trip website.

Traveling by combination of ferry and taxi from Nantucket to Provincetown takes 3 hours. Alternatively, you can do a combination of ferry and bus. In August, daily temperatures in Provincetown can reach 30°C, while at night they dip to 19°C. Wrap up your sightseeing on the 8th (Mon) early enough to fly back home.
more
Parks · Outdoors · Beaches · Historic Sites
Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Nightlife
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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