14 days in Maine Itinerary

14 days in Maine Itinerary

Created using Inspirock Maine trip itinerary planner
©
Make it your trip
Fly
1
Portland
— 4 nights
Drive
2
Boothbay Harbor
— 4 nights
Drive
3
Bar Harbor, Mount Desert Island
— 5 nights
Fly

S M T W T F S
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Portland — 4 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.
Change things up with these side-trips from Portland: Nubble Lighthouse (in York) and Ogunquit (Perkins Cove, Marginal Way Walkway, &more). And it doesn't end there: sample some tasty brews at a beer tour and tasting, sample the tasty concoctions at Allagash Brewing Company, enjoy the sand and surf at Old Orchard Beach, and explore the world behind art at Portland Museum of Art.

For reviews, other places to visit, photos, and other tourist information, read Portland road trip app.

Fort Wayne to Portland is an approximately 6.5-hour flight. You can also drive; or take a bus. While traveling from Fort Wayne, expect little chillier days and about the same nights in Portland, ranging from highs of 53°F to lows of 34°F. Finish up your sightseeing early on the 28th (Thu) so you can go by car to Boothbay Harbor.
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Historic Sites · Parks · Breweries & Distilleries · Outdoors
Side Trips

Boothbay Harbor — 4 nights

Boothbay Harbor is a town in Lincoln County, Maine, United States. Venture out of the city with trips to Mount Battie (in Camden), Cellardoor Winery (in Lincolnville) and Rockland (Farnsworth Art Museum & Rockland Breakwater Light). There's lots more to do: visit a coastal fixture at Pemaquid Point Lighthouse, contemplate the long history of The Wilson Memorial Chapel, examine the collection at Owls Head Transportation Museum, and explore and take pictures at Coastal Maine Botanical Gardens.

For reviews, traveler tips, photos, and tourist information, you can read our Boothbay Harbor road trip planning app.

Drive from Portland to Boothbay Harbor in 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of train and taxi. In April, daily temperatures in Boothbay Harbor can reach 53°F, while at night they dip to 33°F. Wrap up your sightseeing on the 2nd (Mon) to allow time to drive to Bar Harbor.
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Historic Sites · Museums · Parks · Wildlife
Side Trips

Bar Harbor, Mount Desert Island — 5 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Change things up with these side-trips from Bar Harbor: Schoodic Point (in Winter Harbor), Bass Harbor Head Lighthouse (in Bass Harbor) and Catherine Hill Winery (in Cherryfield). Next up on the itinerary: tour the pleasant surroundings at Ocean Path, contemplate the waterfront views at Frenchman Bay, explore the striking landscape at Thunder Hole, and hike along Champlain Mountain & Beehive Loop Trail.

For ratings, more things to do, other places to visit, and tourist information, you can read our Bar Harbor travel planning site.

You can drive from Boothbay Harbor to Bar Harbor in 3 hours. Another option is to do a combination of taxi and bus. May in Bar Harbor sees daily highs of 60°F and lows of 43°F at night. Wrap up your sightseeing on the 7th (Sat) to allow time to fly back home.
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Parks · Outdoors · Trails · Nature
Side Trips

Maine travel guide

4.6
Beaches · Lighthouses · Gift & Specialty Shops
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.
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