57 days in Maine & Key West Itinerary

57 days in Maine & Key West Itinerary

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Route & dates

57 days in Maine & Key West Itinerary

Start: Boston
Drive:  1​h 30​min
1
Ogunquit
— 6 nights
Drive:  3​h 15​min
2
Rangeley
— 6 nights
Drive:  1​h 15​min
3
Farmington
— 3 nights
Drive:  1​h 45​min
4
Boothbay Harbor
— 4 nights
Drive:  1​h 15​min
5
Camden
— 6 nights
Drive:  1​h 45​min
6
Bar Harbor, Mount Desert Island
— 8 nights
Drive:  1​h
7
Winter Harbor
— 4 nights
Drive:  1​h 15​min
8
Bangor
— 6 nights
Fly:  6​h 45​min
9
Key West
— 13 nights
Fly:  6​h 30​min
End: Boston

6
nights
Ogunquit

Ogunquit ©
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.
Explore the numerous day-trip ideas around Ogunquit: Portland (Diamond Cove, Red Claws Basketball, & more), Tributary Brewing (in Kittery) and Harris Farm Cross Country Skiing (in Dayton). There's lots more to do: get to know the fascinating history of Marginal Way Walkway, brush up on your military savvy at Maine Military Museum, see the interesting displays at Portland Head Light, and hit the slopes at Shawnee Peak.

To see maps, traveler tips, and other tourist information, refer to the Ogunquit online itinerary planner .

Boston to Ogunquit is an approximately 1.5-hour car ride. You can also take a train; or take a bus. Traveling from Boston in January, expect Ogunquit to be a bit cooler, temps between 32°F and 12°F. Finish up your sightseeing early on the 21st (Tue) so you can travel to Rangeley.

Things to do in Ogunquit

Outdoors Parks Historic Sites

Side Trips

Portland, South Portland, York, Biddeford, Scalawags Pet Boutique
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Shawnee Peak ©
Shawnee Peak

6
nights
Rangeley

Rangeley ©
Rangeley is a town in Franklin County, Maine, USA. Get out of town with these interesting Rangeley side-trips: Black Mountain of Maine (in Rumford), Attean Overlook (in Jackman) and Sugarloaf Mountain (in Carrabassett Valley). The adventure continues: hit the slopes at Saddleback Maine, get to know the fascinating history of Mount Will Walking Trail, cruise along Height of Land, and see the interesting displays at Maine Forestry Museum.

To find reviews, ratings, more things to do, and more tourist information, you can read our Rangeley online tour itinerary maker .

Drive from Ogunquit to Rangeley in 3.5 hours. Prepare for slightly colder weather when traveling from Ogunquit in January: high temperatures in Rangeley hover around 27°F and lows are around 5°F. Finish up your sightseeing early on the 27th (Mon) so you can travel to Farmington.

Things to do in Rangeley

Parks Outdoors Winter Sports

Side Trips

Bethel, Mount Kineo, Black Mountain of Maine, Step Falls Preserve Hiking Trail, Sugarloaf Mountain
Highlights from your plan
Black Mountain of Maine ©
Black Mountain of Maine
Saddleback Maine ©
Saddleback Maine
Sugarloaf Mountain ©
Sugarloaf Mountain

3
nights
Farmington

Farmington ©
Farmington is a town in and the county seat of Franklin County, Maine, United States. Get out of town with these interesting Farmington side-trips: Tumbledown Mountain (in Weld), Mt. Phillip (in Rome) and Waterville (Quarry Road Trails & Colby College Museum of Art). There's lots more to do: tour the pleasant surroundings at Titcomb Mountain, get engrossed in the history at Stanley Museum, take in the views from The Wire Bridge, and see the interesting displays at Nordica Homestead Museum.

To find ratings, reviews, maps, and more tourist information, refer to the Farmington trip planner .

Getting from Rangeley to Farmington by car takes about an hour. Expect a bit warmer evenings in Farmington when traveling from Rangeley in January, with lows around 12°F. Wrap up your sightseeing on the 30th (Thu) early enough to travel to Boothbay Harbor.

Things to do in Farmington

Parks Outdoors Winter Sports

Side Trips

Waterville, Stanley Museum, Tumbledown Mountain, Mt. Phillip, The Wire Bridge
Highlights from your plan
Quarry Road Trails ©
Quarry Road Trails
Titcomb Mountain ©
Titcomb Mountain
Tumbledown Mountain ©
Tumbledown Mountain

4
nights
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. Get out of town with these interesting Boothbay Harbor side-trips: rendall Fine Art (in Wiscasset), Streaked Mountain (in South Paris) and High View Farm (in Harrison). Next up on the itinerary: take in nature's colorful creations at Coastal Maine Botanical Gardens, admire the engineering at The Swimming Hole At Bristol Dam, step off the mainland to explore Damariscove Island, and contemplate in the serene atmosphere at First Parish Church.

For ratings, photos, reviews, and tourist information, go to the Boothbay Harbor trip itinerary planning tool .

You can drive from Farmington to Boothbay Harbor in 2 hours. In January in Boothbay Harbor, expect temperatures between 32°F during the day and 14°F at night. Finish up your sightseeing early on the 3rd (Mon) so you can go by car to Camden.

Things to do in Boothbay Harbor

Parks Nature Wildlife

Side Trips

Eagle Island, rendall Fine Art, The Swimming Hole At Bristol Dam, Coastal Maine Botanical Gardens, First Parish Church
Highlights from your plan
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens
Damariscove Island ©
Damariscove Island

6
nights
Camden

Camden ©
Camden is a town in Knox County, Maine, United States. Explore the numerous day-trip ideas around Camden: Duck Harbor Mountain (in Isle Au Haut), Jonathan Fisher House (in Blue Hill) and Friend Memorial Public Library (in Brooklin). And it doesn't end there: see the interesting displays at Owls Head Transportation Museum, do a tasting at Sweetgrass Winery and Distillery, stop by Jo Ellen Designs, and take in the awesome beauty at Bald Mountain Preserve.

For photos, reviews, ratings, and tourist information, you can read our Camden travel route builder website .

Traveling by car from Boothbay Harbor to Camden takes 1.5 hours. Alternatively, you can do a combination of taxi and bus. February in Camden sees daily highs of 33°F and lows of 16°F at night. Wrap up your sightseeing on the 9th (Sun) to allow time to drive to Bar Harbor.

Things to do in Camden

Parks Nature Museums

Side Trips

Rockport, Northport Landing Gallery & Espresso Bar, Haynes Gallery, Olson House, Northern Solstice Alpaca Farm
Highlights from your plan
Bald Mountain Preserve ©
Bald Mountain Preserve
Friend Memorial Public Library ©
Friend Memorial Public Library
Owls Head Transportation Museum ©
Owls Head Transportation Museum

8
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Get out of town with these interesting Bar Harbor side-trips: Swans Island (in Bass Harbor) and Southwest Harbor (Wendell Gilley Museum, Mansell Mountain, & more). Spend the 11th (Tue) exploring nature at Acadia National Park. The adventure continues: step off the mainland to explore Mount Desert Island, hike along Beech Cliff Loop, take your sightseeing to a higher altitude at Day Mountain, and tour the pleasant surroundings at Jordan Cliffs Trail.

To find ratings, more things to do, traveler tips, and more tourist information, go to the Bar Harbor travel route planning website .

Traveling by car from Camden to Bar Harbor takes 2 hours. Alternatively, you can take a bus. In February in Bar Harbor, expect temperatures between 33°F during the day and 15°F at night. Cap off your sightseeing on the 17th (Mon) early enough to go by car to Winter Harbor.

Things to do in Bar Harbor

Parks Nature Outdoors

Side Trips

Southwest Harbor, Acadia National Park, Mount Desert Island, Swans Island
Highlights from your plan
Pemetic Mountain ©
Pemetic Mountain
Mansell Mountain ©
Mansell Mountain
Day Mountain ©
Day Mountain

4
nights
Winter Harbor

Winter Harbor ©
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. Venture out of the city with trips to Sullivan (The Granite Garden Gallery & Spring Woods Gallery) and Seal Harbor (Naturalist's Notebook & Abby Aldrich Rockefeller Garden). Spend the 21st (Fri) exploring nature at Schoodic Institute at Acadia National Park. There's much more to do: take a memorable drive along Schoodic National Scenic Byway, do a tasting at Bartlett Maine Estate Winery, view the masterpieces at Whopaints Gallery, and take your sightseeing to a higher altitude at Schoodic Mountain.

Find out how to plan Winter Harbor trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Bar Harbor to Winter Harbor takes an hour. In February, daily temperatures in Winter Harbor can reach 33°F, while at night they dip to 15°F. Finish your sightseeing early on the 21st (Fri) so you can drive to Bangor.

Things to do in Winter Harbor

Parks Nature Wildlife

Side Trips

Gouldsboro, Sullivan, Seal Harbor
Highlights from your plan
Schoodic Point ©
Schoodic Point
Schoodic National Scenic Byway ©
Schoodic National Scenic Byway
Naturalist's Notebook ©
Naturalist's Notebook

6
nights
Bangor

Bangor ©
Bangor is a city along the Penobscot River in the U.S. Explore the numerous day-trip ideas around Bangor: The Telephone Museum (in Ellsworth), Stewart's Blueberries (in Stockton Springs) and Bucksport (Bucksport Waterfront Walkway & Bucksport Historical Society). There's lots more to do: explore the different monuments and memorials at Mount Hope Garden Cemetery, look for gifts at The Blue Hill Wine Shop, take an in-depth tour of Skowhegan History House Museum, and get a taste of the local shopping with Wild Mountain Man Ray's Chainsaw Show.

To see other places to visit, ratings, photos, and more tourist information, you can read our Bangor online travel route planner .

Traveling by car from Winter Harbor to Bangor takes 1.5 hours. Plan for a bit cooler nights when traveling from Winter Harbor in February since evenings lows in Bangor dip to 9°F. Wrap up your sightseeing on the 27th (Thu) to allow time to travel to Key West.

Things to do in Bangor

Museums Parks Outdoors

Side Trips

Orono, Bucksport, Skowhegan History House Museum, Stewart's Blueberries, Wreaths Across America Museum
Highlights from your plan
Moosehead Historical Society ©
Moosehead Historical Society
Mount Hope Garden Cemetery ©
Mount Hope Garden Cemetery
Orono Bog Boardwalk ©
Orono Bog Boardwalk

13
nights
Key West

Key West ©
Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Change things up with a short trip to National Key Deer Refuge in Big Pine Key (about 50 minutes away). Spend the 1st (Sun) exploring nature at Dry Tortugas National Park. There's still lots to do: see the interesting displays at The Ernest Hemingway Home and Museum, glide through the air with a parasailing or paragliding tour, don't miss a visit to Duval Street, and explore and take pictures at The Overseas Highway.

To see photos, more things to do, where to stay, and other tourist information, go to the Key West trip itinerary planner.

Fly from Bangor to Key West in 7 hours. Alternatively, you can drive; or do a combination of bus and train. In February, Key West is much warmer than Bangor - with highs of 78°F and lows of 68°F. Wrap up your sightseeing by early afternoon on the 11th (Wed) to allow time for travel back home.

Things to do in Key West

Outdoors Tours Wildlife

Side Trip

National Key Deer Refuge
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Duval Street ©
Duval Street

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