14 days in New England Itinerary

14 days in New England Itinerary

Created using Inspirock New England tour itinerary builder
Make it your trip
Fly
1
Newport
— 2 nights
Drive
2
Hyannis
— 3 nights
Drive
3
Boston
— 3 nights
Drive
4
Ogunquit
— 1 night
Drive
5
Boothbay Harbor
— 2 nights
Drive
6
Bar Harbor, Mount Desert Island
— 2 nights
Fly

S M T W T F S
28
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Newport — 2 nights

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Escape the urban bustle at Cliff Walk and Boat Tours & Water Sports. Get some historical perspective at Ocean Drive Historic District and Fort Adams State Park. Change things up with a short trip to Crescent Park Looff Carousel in Riverside (about 54 minutes away). There's more to do: see the interesting displays at The Breakers.

You can plan Newport trip in no time by asking Inspirock to help create your itinerary.

Newark to Newport is an approximately 3-hour flight. You can also drive; or do a combination of train and bus. Traveling from Newark in August, expect Newport to be a bit cooler, temps between 79°F and 63°F. Wrap up your sightseeing on the 30th (Tue) early enough to drive to Hyannis.
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Historic Sites · Outdoors · Museums · Parks
Side Trips

Hyannis — 3 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Your inner history buff will appreciate Atwood Museum and Edward Gorey House. Do some cultural sightseeing at Heritage Museums & Gardens and Captain Bangs Hallet House Museum. When in Hyannis, make a side trip to see Shining Sea Bikeway in Falmouth, approximately Falmouth away. Spend the 1st (Thu) exploring nature at Cape Cod National Seashore. There's still lots to do: get up close to creatures of the deep with Hyannis Whale Watcher Cruises.

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

Getting from Newport to Hyannis by car takes about 2 hours. Other options: take a bus. Expect a daytime high around 79°F in August, and nighttime lows around 63°F. Finish your sightseeing early on the 2nd (Fri) to allow enough time to drive to Boston.
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Outdoors · Parks · Nature · Beaches
Side Trips

Boston — 3 nights

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.
Get some cultural insight at Freedom Trail and John F. Kennedy Presidential Museum & Library. Take a break from Boston with a short trip to Dolphin & Whale Watching in Gloucester, about 50 minutes away. There's lots more to do: explore the world behind art at Museum of Fine Arts, explore the different monuments and memorials at Mount Auburn Cemetery, take in nature's colorful creations at Boston Public Garden, and explore the galleries of Boston Tea Party Ships & Museum.

To see photos, traveler tips, reviews, and tourist information, read our Boston travel route tool.

Traveling by car from Hyannis to Boston takes 1.5 hours. Alternatively, you can take a bus; or fly. September in Boston sees daily highs of 75°F and lows of 59°F at night. Wrap up your sightseeing on the 5th (Mon) early enough to drive to Ogunquit.
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Museums · Outdoors · Wildlife · Historic Sites
Side Trips

Ogunquit — 1 night

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.
Kick off your visit on the 6th (Tue): get a new perspective on things with Boat Tours & Water Sports, then enjoy the sand and surf at Ogunquit Beach, and then get to know the fascinating history of Marginal Way Walkway.

To see maps, more things to do, traveler tips, and more tourist information, you can read our Ogunquit itinerary planner.

Traveling by car from Boston to Ogunquit takes 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect a bit cooler evenings in Ogunquit when traveling from Boston in September, with lows around 48°F. Cap off your sightseeing on the 6th (Tue) early enough to go by car to Boothbay Harbor.
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Outdoors · Beaches · Historic Sites · Parks
Side Trip

Boothbay Harbor — 2 nights

Boothbay Harbor is a town in Lincoln County, Maine, United States. Start off your visit on the 7th (Wed): pause for some serene contemplation at The Wilson Memorial Chapel, enjoy the sea views from Pemaquid Point Lighthouse, and then see majestic marine mammals with Cap'n Fish's Cruises. Here are some ideas for day two: head off the coast to Cabbage Island and then go for a walk through Coastal Maine Botanical Gardens.

To see ratings, other places to visit, traveler tips, and other tourist information, refer to the Boothbay Harbor vacation planner.

Getting from Ogunquit to Boothbay Harbor by car takes about 2 hours. Other options: do a combination of taxi and train. In September, daytime highs in Boothbay Harbor are 73°F, while nighttime lows are 51°F. Wrap up your sightseeing on the 8th (Thu) to allow time to drive to Bar Harbor.
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Historic Sites · Parks · Wildlife · Nature
Side Trips

Bar Harbor, Mount Desert Island — 2 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 9th (Fri): examine the collection at Maine Granite Industry Museum, then trek along Precipice Trail, and then take a tour by water with Boat Tours & Water Sports. On the 10th (Sat), you'll have a packed day of sightseeing: take your sightseeing to a higher altitude at Cadillac Mountain, then hike along Champlain Mountain & Beehive Loop Trail, and then learn about winemaking at Catherine Hill Winery.

To find ratings, where to stay, traveler tips, and other tourist information, read Bar Harbor attractions planner.

Drive from Boothbay Harbor to Bar Harbor in 3 hours. Alternatively, you can do a combination of taxi and bus. In September in Bar Harbor, expect temperatures between 70°F during the day and 52°F at night. Finish your sightseeing early on the 10th (Sat) to allow enough time to fly back home.
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Outdoors · Parks · Trails · Nature
Side Trips