14 days in New England Itinerary

Created using Klarna Trips New England tour itinerary maker
Make it your trip
Fly
1
Portland
— 2 nights
Drive
2
North Conway
— 1 night
Drive
3
Rockland
— 2 nights
Drive
4
Bar Harbor, Mount Desert Island
— 3 nights
Fly
5
Newport
— 3 nights
Drive
6
Boston
— 2 nights
Fly

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Portland — 2 nights

The Forest City

Kick off your visit on the 3rd (Wed): explore the landscape on two wheels at Eastern Promenade Trail, see what you can catch with a fishing tour, then get engrossed in the history at Victoria Mansion, and finally revel in the low prices at L.L. Bean Factory Store. Keep things going the next day: take an in-depth tour of Strawbery Banke Museum, then take in the exciting artwork at Ogunquit Museum of American Art, and then kick back and relax at Wells Beach.

To find traveler tips, ratings, other places to visit, and tourist information, go to the Portland visit planner.

Buenos Aires, Argentina to Portland is an approximately 16.5-hour flight. Traveling from Buenos Aires to Portland, you'll gain 2 hours due to the time zone difference. Traveling from Buenos Aires in May, expect a bit cooler with lows of 8°C in Portland. Finish up your sightseeing early on the 4th (Thu) so you can go by car to North Conway.
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North Conway — 1 night

Start off your visit on the 5th (Fri): ski along the peaceful trails at Great Glen Trails Outdoor Center, learn about winemaking at White Mountain Winery, then explore the striking landscape at Cathedral Ledge, and finally stop by Zeb's General Store.

To find more things to do, traveler tips, ratings, and more tourist information, read North Conway trip app.

Drive from Portland to North Conway in 2 hours. Alternatively, you can do a combination of bus and taxi. Traveling from Portland in May, you will find days in North Conway are a bit cooler (17°C), and nights are about the same (7°C). Finish your sightseeing early on the 5th (Fri) so you can drive to Rockland.
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Rockland — 2 nights

On the 6th (Sat), get all the information you need at Project Puffin Visitor Center, visit a coastal fixture at Rockland Breakwater Light, then admire the majestic nature at Camden Hills State Park, and finally take a tour by water with Boat Tours & Water Sports. Get ready for a full day of sightseeing on the 7th (Sun): admire the masterpieces at Farnsworth Art Museum, then see the interesting displays at Owls Head Transportation Museum, and then enjoy the sea views from Owls Head Lighthouse.

To see maps, other places to visit, ratings, and other tourist information, use the Rockland driving holiday planner.

Traveling by car from North Conway to Rockland takes 3 hours. Alternatively, you can do a combination of car and bus; or take a bus. In May, plan for daily highs up to 17°C, and evening lows to 7°C. Finish your sightseeing early on the 7th (Sun) to allow enough time to drive to Bar Harbor.
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Bar Harbor, Mount Desert Island — 3 nights

Escape the urban bustle at Sand Beach and Photography Tours. Explore hidden gems such as Kayaking & Canoeing and Gorham Mountain Trail.

To see photos, ratings, and other tourist information, refer to the Bar Harbor trip maker app.

You can drive from Rockland to Bar Harbor in 2.5 hours. Alternatively, you can take a bus. May in Bar Harbor sees daily highs of 18°C and lows of 7°C at night. Wrap up your sightseeing on the 10th (Wed) to allow time to fly to Newport.
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Newport — 3 nights

City by the Sea

You'll explore and learn at Lizzie Borden House and Rough Point Museum. Step off the beaten path and head to Fort Adams State Park and The Jenney. Get out of town with these interesting Newport side-trips: New Bedford Whaling Museum (in New Bedford), RISD Museum (in Providence) and Sandwich (Sandwich Glass Museum & Heritage Museums & Gardens). There's more to do: examine the collection at International Tennis Hall of Fame.

To see maps, reviews, other places to visit, and tourist information, go to the Newport trip maker site.

Fly from Bar Harbor to Newport in 3 hours. Alternatively, you can drive; or take a bus. Expect a bit warmer evenings in Newport when traveling from Bar Harbor in May, with lows around 11°C. Finish up your sightseeing early on the 13th (Sat) so you can go by car to Boston.
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Find places to stay May 10 — 13:

Boston — 2 nights

Beantown

On the 14th (Sun), get a sense of history and politics at Old State House, contemplate the long history of Granary Burying Ground, wander the streets of Waterfront, then learn more about the world around you at The Harvard Museum of Natural History, and finally step aboard Charlestown Navy Yard.

For reviews, ratings, where to stay, and tourist information, refer to the Boston travel planner.

You can drive from Newport to Boston in 2 hours. Alternatively, you can drive; or take a bus; or do a combination of bus and train. In May, daytime highs in Boston are 22°C, while nighttime lows are 11°C. Wrap up your sightseeing on the 15th (Mon) to allow time to fly back home.
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