31 days in New England Itinerary

31 days in New England Itinerary

Created using Inspirock New England trip itinerary maker

Make it your trip
Fly
1
North Conway
— 3 nights
Drive
2
Camden
— 4 nights
Drive
3
Ogunquit
— 3 nights
Drive
4
Provincetown
— 4 nights
Fly
5
Boston
— 6 nights
Drive
6
Sandwich
— 3 nights
Drive
7
Newport
— 5 nights
Drive
8
Westfield
— 2 nights
Drive to Bradley International Airport, Fly to Orlando

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North Conway

— 3 nights
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Change things up with these side-trips from North Conway: Dog Mountain Home of Stephen Huneck Gallery (in Saint Johnsbury), Wright Museum of WWII (in Wolfeboro) and West Rattlesnake Mountain (in Holderness). There's lots more to do: find something for the whole family at Santa's Village, get a dose of the wild on Bretton Woods Canopy Tour, get to know the fascinating history of Flume Gorge, and take in the dramatic scenery at Diana's Baths.

For other places to visit, photos, ratings, and more tourist information, refer to the North Conway tour itinerary planner.

Orlando to North Conway is an approximately 5-hour flight. You can also drive; or do a combination of train and bus. Expect colder temperatures when traveling from Orlando in May; daily highs in North Conway reach 59°F and lows reach 43°F. Wrap up your sightseeing on the 4th (Tue) early enough to drive to Camden.

Things to do in North Conway

Parks · Nature · Outdoors · Scenic Drive

Side Trips

Camden

— 4 nights
Explore the numerous day-trip ideas around Camden: Pemaquid Point Lighthouse (in Bristol), Olson House (in Cushing) and Bar Harbor (Shore Path, Land Bridge to Bar Island, &more).

For other places to visit, where to stay, photos, and more tourist information, read our Camden trip planner.

Traveling by car from North Conway to Camden takes 3.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Expect a daytime high around 59°F in May, and nighttime lows around 43°F. Finish your sightseeing early on the 8th (Sat) to allow enough time to drive to Ogunquit.

Things to do in Camden

Parks · Nature · Museums · Outdoors

Side Trips

Ogunquit

— 3 nights
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Change things up with these side-trips from Ogunquit: Cape Elizabeth (Fort Williams Park & Portland Head Light), Portland (The Maine Brew Bus, Portland Museum of Art, &more) and Greenbelt Walkway (in South Portland). The adventure continues: get to know the fascinating history of Marginal Way Walkway, take in the dramatic natural features at Perkins Cove, tour the pleasant surroundings at Ogunquit Beach, and take advantage of the amenities at Old Orchard Beach.

To see photos, other places to visit, traveler tips, and tourist information, refer to the Ogunquit trip maker tool.

Traveling by car from Camden to Ogunquit takes 2.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus, train, and taxi. Expect somewhat warmer weather when traveling from Camden in May: highs in Ogunquit hover around 66°F, while lows dip to 43°F. Finish up your sightseeing early on the 11th (Tue) so you can go by car to Provincetown.

Things to do in Ogunquit

Parks · Outdoors · Tours · Historic Sites

Side Trips

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.
Change things up with these side-trips from Provincetown: Nauset Beach (in Orleans) and Eastham (Coast Guard Beach, Salt Pond Visitor Center, &more). Next up on the itinerary: appreciate the history behind Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Long Point, stroll through Herring Cove Beach, and make a trip to Commercial Street.

To find more things to do, where to stay, other places to visit, and more tourist information, use the Provincetown trip itinerary planning app.

You can drive from Ogunquit to Provincetown in 4 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of taxi, train, and ferry. In May, daytime highs in Provincetown are 63°F, while nighttime lows are 48°F. Finish your sightseeing early on the 15th (Sat) so you can fly to Boston.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Boston

— 6 nights

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.
Explore the numerous day-trip ideas around Boston: Salem (Peabody Essex Museum & Salem Witch Museum), Dolphin & Whale Watching (in Gloucester) and Cogswell's Grant (in Essex). There's still lots to do: admire the masterpieces at Museum of Fine Arts, browse the exhibits of New England Holocaust Memorial, buy something for everyone on your list at Faneuil Hall Marketplace, and get to know the fascinating history of Freedom Trail.

To see photos, where to stay, and other tourist information, refer to the Boston vacation planner.

Traveling by flight from Provincetown to Boston takes 2 hours. Alternatively, you can ride a ferry; or drive. In May, daytime highs in Boston are 67°F, while nighttime lows are 50°F. Finish your sightseeing early on the 21st (Fri) so you can drive to Sandwich.

Things to do in Boston

Museums · Historic Sites · Parks · Tours

Side Trips

Sandwich

— 3 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Explore the numerous day-trip ideas around Sandwich: New Bedford Whaling Museum (in New Bedford), Spohr Gardens (in Falmouth) and Mytoi (in Edgartown). There's still lots to do: take an in-depth tour of Plimoth Patuxet, tee off at Farm Neck Golf Club, contemplate the long history of Plymouth Rock, and see the interesting displays at Sandwich Glass Museum.

To find reviews, ratings, traveler tips, and tourist information, read our Sandwich trip planner.

Getting from Boston to Sandwich by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 65°F in May, and nighttime lows around 47°F. Cap off your sightseeing on the 24th (Mon) early enough to go by car to Newport.

Things to do in Sandwich

Museums · Outdoors · Tours · Wildlife

Side Trips

Newport

— 5 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Explore Newport's surroundings by going to Chatham Marconi Maritime Center (in North Chatham), Bristol (Independence Park & Colt State Park) and Lizzie Borden House (in Fall River). Next up on the itinerary: see the interesting displays at The Breakers, admire the striking features of Marble House, sample some tasty brews at Rhode Island Red Food Tours, and take a tour by water with Boat Tours & Water Sports.

To find photos, maps, ratings, and more tourist information, use the Newport vacation builder.

Traveling by car from Sandwich to Newport takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 65°F in May, and nighttime lows around 49°F. Cap off your sightseeing on the 29th (Sat) early enough to travel to Westfield.

Things to do in Newport

Historic Sites · Parks · Outdoors · Museums

Side Trips

Westfield

— 2 nights
Westfield is a city in Hampden County, in the Pioneer Valley of western Massachusetts, United States. Start off your visit on the 30th (Sun): find something for the whole family at Six Flags New England, trek along Farmington Valley Greenway, then appreciate the history behind Soldiers' Monument and Memorial Park, then take in the spiritual surroundings of Our Lady of Lourdes' Shrine, and finally take an in-depth tour of Hotchkiss-Fyler House Museum. On the 31st (Mon), you'll have a packed day of sightseeing: walk around Stanley park, admire the natural beauty at Grandmother's Garden, then examine the collection at Chester Railway Station, and finally admire the natural beauty at Three Sisters Sanctuary.

To find photos, traveler tips, reviews, and more tourist information, read our Westfield online route planner.

You can drive from Newport to Westfield in 2.5 hours. While traveling from Newport, expect a bit warmer days and about the same nights in Westfield, ranging from highs of 72°F to lows of 48°F. Wrap up your sightseeing on the 31st (Mon) to allow time to travel back home.

Things to do in Westfield

Parks · Museums · Theme Parks · Outdoors

Side Trips