31 days in New England Itinerary

31 days in New England Itinerary

Created using Inspirock New England tour planner

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Route & dates

31 days in New England Itinerary

Start: Orlando
Fly + Drive:  6​h 30​min
1
Boothbay
— 3 nights
Drive:  1​h 45​min
2
Ogunquit
— 4 nights
Drive:  1​h 30​min
3
Boston
— 5 nights
Drive + ferry:  2​h 30​min
4
Nantucket
— 3 nights
Drive:  3​h 15​min
5
Provincetown
— 4 nights
Drive:  1​h 45​min
6
Falmouth
— 3 nights
Drive:  1​h 30​min
7
Newport
— 4 nights
Drive:  2​h
8
Hartford
— 4 nights
Fly:  5​h 45​min
End: Orlando

3
nights
Boothbay

Boothbay ©
Boothbay is a town in Lincoln County, Maine, United States. Explore Boothbay's surroundings by going to Camden (Camden Hills State Park & Mount Battie), Pemaquid Point Lighthouse (in Bristol) and Owls Head Transportation Museum (in Owls Head). There's much more to do: take in nature's colorful creations at Coastal Maine Botanical Gardens, see the interesting displays at Maine Maritime Museum, kick back and relax at Popham Beach State Park, and head off the coast to Cabbage Island.

To see ratings, reviews, traveler tips, and tourist information, read Boothbay online trip itinerary builder .

Orlando to Boothbay is an approximately 6.5-hour combination of flight and car. You can also drive. In May, Boothbay is cooler than Orlando - with highs of 64°F and lows of 44°F. Finish your sightseeing early on the 4th (Mon) so you can drive to Ogunquit.

Things to do in Boothbay

Parks Nature Museums

Side Trips

Camden, Pemaquid Point Lighthouse, Cabbage Island, Popham Beach State Park, Owls Head Transportation Museum
Highlights from your plan
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens
Mount Battie ©
Mount Battie
Pemaquid Point Lighthouse ©
Pemaquid Point Lighthouse

4
nights
Ogunquit

Ogunquit ©
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.
Get out of town with these interesting Ogunquit side-trips: Kancamagus Highway (in North Conway), Portland Head Light (in Cape Elizabeth) and The Little White Church (in Eaton). Next up on the itinerary: appreciate the extensive heritage of Marginal Way Walkway, kick back and relax at Ogunquit Beach, sample the tasty concoctions at Allagash Brewing Company, and take your sightseeing to a higher altitude at West Rattlesnake Mountain.

Before you visit Ogunquit, use our trip planner to discover what you can do and see there.

You can drive from Boothbay to Ogunquit in 2 hours. In May, plan for daily highs up to 66°F, and evening lows to 43°F. Wrap up your sightseeing on the 8th (Fri) to allow time to drive to Boston.

Things to do in Ogunquit

Historic Sites Parks Outdoors

Side Trips

Nubble Lighthouse, The Little White Church, St. Ann's Episcopal Church, West Rattlesnake Mountain, Portland Head Light
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Kancamagus Highway ©
Kancamagus Highway
Portland Head Light ©
Portland Head Light

5
nights
Boston

Boston ©
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.
Change things up with a short trip to Dolphin & Whale Watching in Gloucester (about 50 minutes away). Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, walk around Boston Common, take an in-depth tour of Boston Tea Party Ships & Museum, and get a variety of perspectives on a duck tour.

To find reviews, maps, more things to do, and other tourist information, refer to the Boston itinerary planner.

You can drive from Ogunquit to Boston in 1.5 hours. Other options are to take a train; or take a bus. Traveling from Ogunquit in May, plan for somewhat warmer nights in Boston, with lows around 50°F. Finish your sightseeing early on the 13th (Wed) to allow enough time to travel to Nantucket.

Things to do in Boston

Museums Parks Tours

Side Trip

Dolphin & Whale Watching
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Boston Common ©
Boston Common

3
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Nantucket is known for museums, beaches, historic sites, breweries & distilleries, and outdoors. Your plan includes some of its best attractions: examine the collection at Whaling Museum, don't miss a visit to Nantucket Founders Burial Ground, visit a coastal fixture at Great Point Light, and tee off at Miacomet Golf Club.

Take the guesswork out of planning a Nantucket vacation by using our trip itinerary maker.

Getting from Boston to Nantucket by combination of car and ferry takes about 2.5 hours. Other options: fly; or do a combination of bus and flight. Traveling from Boston in May, you will find days in Nantucket are little chillier (62°F), and nights are about the same (49°F). Wrap up your sightseeing on the 16th (Sat) early enough to drive to Provincetown.

Things to do in Nantucket

Outdoors Historic Sites Museums
Highlights from your plan
Jetties Beach ©
Jetties Beach
Whaling Museum ©
Whaling Museum
Great Point Light ©
Great Point Light

4
nights
Provincetown

Provincetown ©
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 Nauset Beach (in Orleans) and Eastham (Coast Guard Beach & Salt Pond Visitor Center). And it doesn't end there: pause for some photo ops at Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Long Point, stroll through Race Point Beach, and make a trip to Commercial Street.

To see more things to do, traveler tips, other places to visit, and more tourist information, go to the Provincetown trip planner.

You can drive from Nantucket to Provincetown in 3.5 hours. In May, daytime highs in Provincetown are 63°F, while nighttime lows are 48°F. Finish up your sightseeing early on the 20th (Wed) so you can go by car to Falmouth.

Things to do in Provincetown

Outdoors Beaches Parks

Side Trips

Eastham, Cape Cod National Seashore, Marconi Beach, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©
Race Point Beach ©
Race Point Beach

3
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Venture out of the city with trips to Cape Cod Canal (in Buzzards Bay), Sandwich (Heritage Museums & Gardens & Old King's Hwy) and Plymouth (Plimoth Plantation & Plymouth Rock). There's much more to do: explore the landscape on two wheels at Shining Sea Bikeway, admire the natural beauty at Spohr Gardens, stroll through Old Silver Beach, and visit a coastal fixture at Nobska Point Lighthouse.

To find reviews, photos, where to stay, and more tourist information, use the Falmouth trip itinerary builder website .

Getting from Provincetown to Falmouth by car takes about 2 hours. Other options: take a bus. In May in Falmouth, expect temperatures between 65°F during the day and 47°F at night. Finish up your sightseeing early on the 23rd (Sat) so you can go by car to Newport.

Things to do in Falmouth

Museums Parks Outdoors

Side Trips

Sandwich, Plymouth, Cape Cod Canal
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum
Plimoth Plantation ©
Plimoth Plantation

4
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Venture out of the city with trips to Mystic (Mystic Aquarium & Mystic Seaport Museum), Chatham Marconi Maritime Center (in North Chatham) and Monomoy National Wildlife Refuge (in Chatham). There's much more to do: examine the collection at The Breakers, stroll through The Farmer's Daughter, browse the exhibits of Lizzie Borden House, and test your team's savvy at popular escape rooms.

For photos, other places to visit, traveler tips, and other tourist information, you can read our Newport day trip planner .

You can drive from Falmouth to Newport in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, plan for daily highs up to 65°F, and evening lows to 49°F. Cap off your sightseeing on the 27th (Wed) early enough to go by car to Hartford.

Things to do in Newport

Museums Parks Historic Sites

Side Trips

Mystic, Chatham, New Bedford Whaling Museum, Room Escape Games, Lizzie Borden House
Highlights from your plan
The Breakers ©
The Breakers
Mystic Seaport Museum ©
Mystic Seaport Museum
Ocean Drive Historic District ©
Ocean Drive Historic District

4
nights
Hartford

Hartford ©
Hartford is the capital of the U.S. Explore Hartford's surroundings by going to Dr. Seuss National Memorial Sculpture Garden (in Springfield), Stanley park (in Westfield) and The Clark Art Institute (in Williamstown). There's still lots to do: explore the world behind art at Norman Rockwell Museum, don't miss a visit to Connecticut Fallen Firefighters Memorial, steep yourself in history at Hyland House Museum, and browse the collection at Beinecke Rare Book & Manuscript Library.

To see reviews, where to stay, traveler tips, and other tourist information, refer to the Hartford trip itinerary maker website .

Getting from Newport to Hartford by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from Newport in May, expect nights in Hartford to be about the same, around 51°F, while days are somewhat warmer, around 72°F. Wrap up your sightseeing on the 31st (Sun) to allow time to travel back home.

Things to do in Hartford

Museums Historic Sites Parks

Side Trips

New Haven, US Submarine Veterans of WWII National Memorial East, Stanley park, Connecticut Fallen Firefighters Memorial, Foxwoods Resort Casino
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Stanley park ©
Stanley park
Norman Rockwell Museum ©
Norman Rockwell Museum

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