30 days in Maine Itinerary

30 days in Maine Itinerary

Created using Inspirock Maine vacation maker
©
Make it your trip
Fly
1
Bar Harbor, Mount Desert Island
— 4 nights
Drive
2
Winter Harbor
— 4 nights
Drive
3
Bangor
— 5 nights
Drive
4
Boothbay Harbor
— 5 nights
Drive
5
Portland
— 11 nights
Fly

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Bar Harbor, Mount Desert Island — 4 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Bar Harbor is known for parks, wildlife, and trails. Your trip includes some of its best attractions: stroll through Shore Path, walk around Village Green, trek along Great Head Trail, and get a new perspective on things with Boat Tours & Water Sports.

To find photos, traveler tips, reviews, and more tourist information, refer to the Bar Harbor attractions planner.

New York City to Bar Harbor is an approximately 3-hour flight. You can also drive; or do a combination of train and bus. Prepare for little chillier weather when traveling from New York City in November: high temperatures in Bar Harbor hover around 46°F and lows are around 30°F. Finish up your sightseeing early on the 5th (Fri) so you can go by car to Winter Harbor.
Parks · Outdoors · Trails · Nature
Side Trips

Winter Harbor — 4 nights

Not to be confused with Winter Harbor, Maine the former name of Biddeford PoolWinter Harbor is a town on the Schoodic Peninsula in Hancock County, Maine, United States. Explore the numerous day-trip ideas around Winter Harbor: Lubec (McCurdy Smokehouse Museum & West Quoddy Head Light), Chipman's Wharf (in Milbridge) and Spring Woods Gallery (in Sullivan). There's much more to do: take in the dramatic natural features at Schoodic Point, view the masterpieces at Works of Hand, shop like a local with Chapter Two Art Gallery, and cruise along Schoodic National Scenic Byway.

To find ratings, maps, photos, and more tourist information, read Winter Harbor trip builder website.

You can drive from Bar Harbor to Winter Harbor in an hour. In November, plan for daily highs up to 46°F, and evening lows to 30°F. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Bangor.
Museums · Shopping · Parks · Outdoors
Side Trips

Bangor — 5 nights

Bangor is a city along the Penobscot River in the U.S. state of Maine. You'll find plenty of places to visit near Bangor: Moose Point State Park (in Searsport), Wilson Museum (in Castine) and Belfast (Passy Rail Trail & Belfast City Park). There's much more to do: stroll the grounds of Mount Hope Garden Cemetery, indulge your thirst for a good beer at 2 Feet Brewing, examine the collection at The Telephone Museum, and appreciate the history behind Paul Bunyan Statue.

To find more things to do, photos, and other tourist information, you can read our Bangor day trip planning app.

Traveling by car from Winter Harbor to Bangor takes 1.5 hours. November in Bangor sees daily highs of 46°F and lows of 28°F at night. Finish up your sightseeing early on the 14th (Sun) so you can go by car to Boothbay Harbor.
Museums · Parks · Breweries & Distilleries · Shopping
Side Trips

Boothbay Harbor — 5 nights

Boothbay Harbor is a town in Lincoln County, Maine, United States. You'll find plenty of places to visit near Boothbay Harbor: Bath (Seguin Island and Lighthouse & Maine Maritime Museum), Maine State Museum (in Augusta) and Camden (Ducktrap Bay Trading Co, Mount Battie, &more). Next up on the itinerary: admire the masterpieces at Farnsworth Art Museum, examine the collection at Owls Head Transportation Museum, enjoy the sea views from Owls Head Lighthouse, and tour the pleasant surroundings at Beech Hill Reserve.

Discover how to plan a Boothbay Harbor trip in just a few steps with Inspirock's itinerary builder.

Drive from Bangor to Boothbay Harbor in 2.5 hours. Alternatively, you can do a combination of bus and taxi. In November, plan for daily highs up to 48°F, and evening lows to 29°F. Finish your sightseeing early on the 19th (Fri) to allow enough time to drive to Portland.
Museums · Parks · Historic Sites · Wildlife
Side Trips

Portland — 11 nights

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Explore the numerous day-trip ideas around Portland: Ogunquit (Perkins Cove, Ogunquit Beach, &more), Wells Beach (in Wells) and Kennebunkport (St. Ann's Episcopal Church & Ocean Ave). Next up on the itinerary: savor the flavors at Food & Drink, indulge your thirst for a good beer at Allagash Brewing Company, shop like a local with Harbor Fish Market, and see the interesting displays at Maine Jewish Museum.

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

You can drive from Boothbay Harbor to Portland in 1.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi and train. In November, plan for daily highs up to 49°F, and evening lows to 30°F. Finish your sightseeing early on the 30th (Tue) to allow enough time to fly back home.
Parks · Outdoors · Museums · Breweries & Distilleries
Side Trips

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.