31 days in New England Itinerary

31 days in New England Itinerary

Created using Inspirock New England trip 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:  2​h
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 30​min
5
Provincetown
— 4 nights
Drive:  2​h
6
Falmouth
— 3 nights
Drive:  1​h 30​min
7
Newport
— 4 nights
Drive:  2​h
8
Hartford
— 4 nights
Fly:  6​h
End: Orlando

3
nights
Boothbay

Boothbay ©
Boothbay is a town in Lincoln County, Maine, United States. Change things up with these side-trips from Boothbay: Camden (Camden Hills State Park & Mount Battie), Pemaquid Point Lighthouse (in Bristol) and Owls Head Transportation Museum (in Owls Head). The adventure continues: take in nature's colorful creations at Coastal Maine Botanical Gardens, head off the coast to Cabbage Island, steep yourself in history at The Wilson Memorial Chapel, and see the interesting displays at Maine Maritime Museum.

For more things to do, photos, and tourist information, you can read our Boothbay trip planning website .

Orlando to Boothbay is an approximately 6.5-hour combination of flight and car. You can also drive. Expect much colder temperatures when traveling from Orlando in January; daily highs in Boothbay reach 0°C and lows reach -11°C. Finish your sightseeing early on the 7th (Tue) to allow enough time to drive to Ogunquit.

Things to do in Boothbay

Parks Nature Museums

Side Trips

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

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.
You'll find plenty of places to visit near Ogunquit: Kancamagus Highway (in North Conway), Portland Head Light (in Cape Elizabeth) and The Little White Church (in Eaton). There's still lots to do: get to know the fascinating history of Marginal Way Walkway, take in the architecture and atmosphere at St. Ann's Episcopal Church, indulge your thirst for a good beer at Allagash Brewing Company, and take in the dramatic natural features at Perkins Cove.

To see traveler tips, photos, reviews, and other tourist information, go to the Ogunquit road trip tool .

Traveling by car from Boothbay to Ogunquit takes 2 hours. Expect a daytime high around 0°C in January, and nighttime lows around -13°C. Finish your sightseeing early on the 11th (Sat) to allow enough time to drive to Boston.

Things to do in Ogunquit

Historic Sites Outdoors Parks

Side Trips

St. Ann's Episcopal Church, West Rattlesnake Mountain, Portland Head Light, Kancamagus Highway, The Little White Church
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: explore the world behind art at Museum of Fine Arts, take an in-depth tour of John F. Kennedy Presidential Museum & Library, explore the galleries of Boston Tea Party Ships & Museum, and get to know the fascinating history of Freedom Trail.

For other places to visit, ratings, photos, and other tourist information, read our Boston trip itinerary planner .

You can drive from Ogunquit to Boston in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect somewhat warmer evenings in Boston when traveling from Ogunquit in January, with lows around -5°C. Cap off your sightseeing on the 16th (Thu) early enough 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
Faneuil Hall Marketplace ©
Faneuil Hall Marketplace

3
nights
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: see the interesting displays at Whaling Museum, don't miss a visit to Nantucket Founders Burial Ground, pause for some serene contemplation at St Paul's Episcopal Church, and kick back and relax at Jetties Beach.

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

Traveling by combination of car and ferry from Boston to Nantucket takes 2.5 hours. Alternatively, you can fly; or do a combination of bus and flight. Expect a daytime high around 5°C in January, and nighttime lows around -2°C. Finish your sightseeing early on the 19th (Sun) so you can drive to Provincetown.

Things to do in Nantucket

Outdoors Museums Parks
Highlights from your plan
Fishing Charters & Tours
Whaling Museum ©
Whaling Museum

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). The adventure continues: pause for some photo ops at Pilgrim Monument & Provincetown Museum, make a trip to Commercial Street, enjoy the sand and surf at Marconi Beach, and look for all kinds of wild species at Wildlife Areas.

For more things to do, other places to visit, where to stay, and tourist information, read our Provincetown travel planner .

Traveling by car from Nantucket to Provincetown takes 3.5 hours. In January, daytime highs in Provincetown are 3°C, while nighttime lows are -3°C. Wrap up your sightseeing on the 23rd (Thu) early enough to drive to Falmouth.

Things to do in Provincetown

Outdoors Beaches Parks

Side Trips

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

3
nights
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Explore the numerous day-trip ideas around Falmouth: 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: grab your bike and head to Shining Sea Bikeway, get to know the fascinating history of Cornelia Carey Sanctuary (The Knob), get curious at Sandwich Glass Museum, and admire the natural beauty at Spohr Gardens.

To find photos, where to stay, ratings, and tourist information, read Falmouth trip itinerary site .

Traveling by car from Provincetown to Falmouth takes 2 hours. Alternatively, you can take a bus. Traveling from Provincetown in January, Falmouth is little chillier at night with lows of -6°C. Finish your sightseeing early on the 26th (Sun) so you can drive 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 still lots to do: examine the collection at The Breakers, pause for some serene contemplation at St. Mary's Catholic Church, get to know the fascinating history of Cliff Walk, and steep yourself in history at Lizzie Borden House.

To see maps, traveler tips, ratings, and other tourist information, use the Newport trip itinerary 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 January, daily temperatures in Newport can reach 3°C, while at night they dip to -5°C. Wrap up your sightseeing on the 30th (Thu) to allow time to drive to Hartford.

Things to do in Newport

Museums Parks Historic Sites

Side Trips

Chatham, Mystic, Room Escape Games, The Farmer's Daughter, New Bedford Whaling Museum
Highlights from your plan
The Breakers ©
The Breakers
Ocean Drive Historic District ©
Ocean Drive Historic District
Mystic Seaport Museum ©
Mystic Seaport Museum

4
nights
Hartford

Hartford ©
Hartford is the capital of the U.S. Explore the numerous day-trip ideas around Hartford: Dr. Seuss National Memorial Sculpture Garden (in Springfield), Stanley park (in Westfield) and The Clark Art Institute (in Williamstown). Next up on the itinerary: admire the masterpieces at Norman Rockwell Museum, take in the pleasant sights at Main Street Park, Essex Village, browse the collection at Beinecke Rare Book & Manuscript Library, and appreciate the history behind US Submarine Veterans of WWII National Memorial East.

To find other places to visit, more things to do, photos, and tourist information, use the Hartford online driving holiday planner .

Traveling by car from Newport to Hartford takes 2 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 2°C in January, and nighttime lows around -7°C. Finish up your sightseeing early on the 3rd (Mon) so you can travel back home.

Things to do in Hartford

Museums Historic Sites Parks

Side Trips

New Haven, Dr. Seuss National Memorial Sculpture Garden, The Clark Art Institute, Hyland House Museum, Stanley park
Highlights from your plan
The Clark Art Institute ©
The Clark Art Institute
Stanley park ©
Stanley park
Foxwoods Resort Casino ©
Foxwoods Resort Casino

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