8 days in Maine Itinerary

8 days in Maine Itinerary

Created using Inspirock Maine trip itinerary maker
Make it your trip
Fly to Boston, Bus to Portland
— 1 night
Boothbay Harbor
— 2 nights
Bar Harbor, Mount Desert Island
— 3 nights
— 1 night


Portland — 1 night

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.
Kick off your visit on the 11th (Fri): explore the landscape on two wheels at Greenbelt Walkway, then steep yourself in history at Fort Preble, then look for all kinds of wild species at Spring Point Shoreway, and finally pause for some serene contemplation at The Cathedral Of The Immaculate Conception.

To find more things to do, reviews, other places to visit, and tourist information, read Portland trip planner.

Pittsburgh to Portland is an approximately 6.5-hour combination of flight and bus. You can also do a combination of flight and bus; or drive; or take a bus. In June, Portland is slightly colder than Pittsburgh - with highs of 73°F and lows of 54°F. Finish up your sightseeing early on the 12th (Sat) so you can go by car to Boothbay Harbor.
Outdoors · Parks · Trails · Historic Sites
Side Trip

Boothbay Harbor — 2 nights

Boothbay Harbor is a town in Lincoln County, Maine, United States. On the 12th (Sat), take an in-depth tour of Boothbay Railway Village, explore the historical opulence of Castle Tucker, browse the exhibits of Nickels-Sortwell House, then look for gifts at Eventide Specialties, and finally view the masterpieces at Abacus Gallery. Keep things going the next day: take a stroll around Opera House at Boothbay Harbor, visit a coastal fixture at Burnt Island Lighthouse, then get a taste of the local shopping with Georgetown Pottery, and finally make a trip to Doubling Point Lighthouse.

To see maps, photos, where to stay, and tourist information, read Boothbay Harbor route site.

Traveling by car from Portland to Boothbay Harbor takes 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of train and taxi. June in Boothbay Harbor sees daily highs of 73°F and lows of 52°F at night. Finish your sightseeing early on the 14th (Mon) so you can drive to Bar Harbor.
Museums · Historic Sites · Shopping · Nightlife
Side Trips

Bar Harbor, Mount Desert Island — 3 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Get some cultural insight at St. Saviour's Church : and George B. Dorr Museum of Natural History. Explore hidden gems such as Bar Island Trails and Eagle Lake Acadia National Park. And it doesn't end there: trek along Cadillac Mountain North Ridge Trail, go for a walk through Compass Harbor Trail, head outdoors with Dorr Mountain, and stroll around Agamont Park.

To find maps, reviews, where to stay, and more tourist information, read our Bar Harbor tour planner.

Traveling by car from Boothbay Harbor to Bar Harbor takes 3 hours. Alternatively, you can do a combination of taxi and bus. Traveling from Boothbay Harbor in June, you will find days in Bar Harbor are a bit cooler (68°F), and nights are about the same (52°F). Finish your sightseeing early on the 17th (Thu) to allow enough time to drive to Bangor.
Parks · Outdoors · Trails · Nature
Side Trips

Bangor — 1 night

Bangor is a city along the Penobscot River in the U.S. state of Maine. Kick off your visit on the 17th (Thu): stroll through Kenduskeag Stream Heritage Trail, grab your bike and head to Penobscot River Walkway, then stop by Tea Maineia, then do a tasting at Winterport Winery, and finally browse the different shops at Bangor Mall.

To see ratings, traveler tips, reviews, and other tourist information, refer to the Bangor route planner.

You can drive from Bar Harbor to Bangor in 1.5 hours. Alternatively, you can drive; or take a bus. While traveling from Bar Harbor, expect somewhat warmer days and about the same nights in Bangor, ranging from highs of 74°F to lows of 52°F. Finish your sightseeing early on the 18th (Fri) so you can fly back home.
Outdoors · Shopping · Parks · Wineries
Side Trip

Maine travel guide

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.