16 days in Maine, New York City & Boston Itinerary

16 days in Maine, New York City & Boston Itinerary

Created using Inspirock United States trip itinerary maker

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Monhegan Island
— 1 day
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2
New York City
— 3 nights
Fly to Bangor International Airport, Drive to Lincolnville
3
Lincolnville
— 1 night
Drive
4
Gouldsboro
— 2 nights
Drive
5
Bar Harbor, Mount Desert Island
— 3 nights
Drive
6
Ogunquit
— 2 nights
Drive
7
Boston
— 2 nights
Fly

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Monhegan Island

— 1 day
Kick off your visit on the 25th (Sun): enjoy the sea views from Monhegan Light, then examine the collection at Monhegan Museum, and then view the masterpieces at Lupine Gallery.

To see where to stay, traveler tips, and more tourist information, read Monhegan Island online tour itinerary builder.

Sao Paulo, Brazil to Monhegan Island is an approximately 120-hour travel. The time zone difference when traveling from Sao Paulo to Monhegan Island is minus 2 hours. Traveling from Sao Paulo in November, things will get colder in Monhegan Island: highs are around 9°C and lows about -1°C. Finish your sightseeing early on the 25th (Sun) to allow enough time to travel to New York City.

Things to do in Monhegan Island

Museums · Historic Sites · Shopping

New York City

— 3 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Step off the beaten path and head to Fifth Avenue and New York Public Library. Get some cultural insight at The Metropolitan Museum of Art and 9/11 Memorial. And it doesn't end there: take in the pleasant sights at Times Square, get a new perspective on nature at American Museum of Natural History, admire the masterpieces at Solomon R. Guggenheim Museum, and walk around Central Park.

To see reviews, more things to do, where to stay, and tourist information, read New York City road trip app.

Explore your travel options from Monhegan Island to New York City with the Route module. Traveling from Monhegan Island in November, expect New York City to be a bit warmer, temps between 16°C and 7°C. Finish your sightseeing early on the 28th (Wed) to allow enough time to travel to Lincolnville.

Things to do in New York City

Museums · Parks · Neighborhoods · Shopping

Lincolnville

— 1 night
Lincolnville is a town in Waldo County, Maine, United States. Start off your visit on the 29th (Thu): enjoy the sand and surf at Ducktrap River Park, do a tasting at Cellardoor Winery, then look for gifts at The Smiling Cow, then look for gifts at French & Brawn Market Place, and finally wander the streets of High Street Historic District.

To see where to stay, more things to do, photos, and more tourist information, use the Lincolnville journey planning website.

Use the Route module to find suitable travel options from New York City to Lincolnville. Prepare for little chillier weather when traveling from New York City in November: high temperatures in Lincolnville hover around 9°C and lows are around -1°C. Wrap up your sightseeing on the 29th (Thu) to allow time to drive to Gouldsboro.

Things to do in Lincolnville

Neighborhoods · Historic Sites · Parks · Outdoors

Side Trip

Gouldsboro

— 2 nights
Gouldsboro is a town and municipality in Hancock County, Maine, United States on the Schoodic Peninsula. On the 30th (Fri), shop like a local with Chapter Two Art Gallery, do a tasting at Bartlett Maine Estate Winery, then do a tasting at Catherine Hill Winery, then view the masterpieces at Wild Mountain Man Ray's Chainsaw Show, and finally view the masterpieces at Spring Woods Gallery. Here are some ideas for day two: explore the striking landscape at Schoodic Point, stop by Winter Harbor 5&10, then view the masterpieces at Whopaints Gallery, and finally take a stroll through Grindstone Neck of Maine.

To see traveler tips, where to stay, maps, and more tourist information, go to the Gouldsboro day trip planning website.

Traveling by car from Lincolnville to Gouldsboro takes 2 hours. In November in Gouldsboro, expect temperatures between 9°C during the day and -1°C at night. Wrap up your sightseeing on the 1st (Sat) to allow time to drive to Bar Harbor.

Things to do in Gouldsboro

Shopping · Museums · Parks · Nature

Side Trips

Bar Harbor, Mount Desert Island

— 3 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Explore hidden gems such as Shore Path and A Little Mad. Head to Little Village Gifts and The Rock & Art Shopfor some retail therapy. There's still lots to do: take your sightseeing to a higher altitude at Cadillac Mountain and stop by Manset Little Farm.

To see maps, other places to visit, ratings, and tourist information, read our Bar Harbor day trip planning site.

Traveling by car from Gouldsboro to Bar Harbor takes an hour. Expect a daytime high around 2°C in December, and nighttime lows around -7°C. Wrap up your sightseeing on the 4th (Tue) early enough to drive to Ogunquit.

Things to do in Bar Harbor

Shopping · Parks · Nature · Wildlife

Side Trips

Ogunquit

— 2 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.
On the 5th (Wed), kick back and relax at Wells Beach, then explore the striking landscape at Perkins Cove, and then get to know the fascinating history of Marginal Way Walkway. Here are some ideas for day two: stop by Spoiled Rotten, then enjoy the sand and surf at Ogunquit Beach, and then stroll through Long Sands Beach.

To see reviews, where to stay, and tourist information, go to the Ogunquit trip itinerary planner.

You can drive from Bar Harbor to Ogunquit in 4 hours. Other options are to do a combination of flight and bus; or do a combination of bus, train, and taxi. Expect a daytime high around 2°C in December, and nighttime lows around -9°C. Finish your sightseeing early on the 6th (Thu) so you can drive to Boston.

Things to do in Ogunquit

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Boston

— 2 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.
Start off your visit on the 7th (Fri): stop by Brookline Booksmith, then explore the world behind art at Museum of Fine Arts, then don't miss a visit to Faneuil Hall Marketplace, and finally stop by North End. Keep things going the next day: take a stroll through Waterfront, then take a stroll through Beacon Hill, and then take in nature's colorful creations at Boston Public Garden.

Plan a Boston trip in moments using our itinerary builder.

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Prepare for somewhat warmer weather when traveling from Ogunquit in December: high temperatures in Boston hover around 7°C and lows are around 0°C. Finish up your sightseeing early on the 8th (Sat) so you can travel back home.

Things to do in Boston

Neighborhoods · Museums · Shopping · Parks

Side Trip

Maine travel guide

4.6
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.