52 days in Maine Itinerary

52 days in Maine Itinerary

Created using Inspirock Maine trip planner

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Route & dates

52 days in Maine Itinerary

Start: Milan
+2
Drive + Fly + Drive:  16​h 15​min
1
Boothbay
— 9 nights
Drive:  2​h
2
Ogunquit
— 10 nights
Drive:  2​h 30​min
3
Rockland
— 10 nights
Drive:  3​h 15​min
4
Lubec
— 9 nights
Drive:  2​h 30​min
5
Bar Harbor, Mount Desert Island
— 11 nights
+2
shuttle + bus + Fly:  15​h 15​min
End: Milan

9
nights
Boothbay

Boothbay ©
Boothbay is a town in Lincoln County, Maine, United States. Your cultural itinerary includes sights like Pemaquid Point Lighthouse and Maine Maritime Museum. Step out of the city life by going to Popham Beach State Park and Cabbage Island. Explore Boothbay's surroundings by going to Eagle Island (in Harpswell), Freeport (Wolfe's Neck Woods State Park & L.L. Bean Factory Store) and Reid State Park (in Georgetown). Next up on the itinerary: take in nature's colorful creations at Coastal Maine Botanical Gardens, hunt for treasures at Boothbay Farmers' Market, step off the mainland to explore Mackworth Island, and enjoy the sand and surf at Pemaquid Beach Park.

To see more things to do, reviews, other places to visit, and more tourist information, use the Boothbay trip planner.

Milan, Italy to Boothbay is an approximately 16.5-hour flight. You'll gain 6 hours traveling from Milan to Boothbay due to the time zone difference. Expect a bit cooler evenings in Boothbay when traveling from Milan in September, with lows around 12°C. Wrap up your sightseeing on the 18th (Tue) early enough to travel to Ogunquit.

Things to do in Boothbay

Parks Nature Outdoors

Side Trips

Boothbay Harbor, Bristol, Freeport, Augusta, Popham Beach State Park
Highlights from your plan
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens
Pemaquid Point Lighthouse ©
Pemaquid Point Lighthouse
Popham Beach State Park ©
Popham Beach State Park

10
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.
Get some cultural insight at Marginal Way Walkway and Portland Head Light. Get some historical perspective at Cape Neddick Nubble Lighthouse and Mount Agamenticus. Explore Ogunquit's surroundings by going to Old Orchard Beach (in Old Orchard Beach), Fortunes Rocks Beach (in Biddeford) and Portland (Allagash Brewery, Austin Street Brewery, & more). Next up on the itinerary: kick back and relax at Ogunquit Beach, stroll through Drakes Island Beach, explore the striking landscape at Perkins Cove, and identify plant and animal life at Rachel Carson National Wildlife Refuge.

To find reviews, ratings, traveler tips, and more tourist information, you can read our Ogunquit journey website .

Traveling by car from Boothbay to Ogunquit takes 2 hours. In September, plan for daily highs up to 27°C, and evening lows to 10°C. Wrap up your sightseeing on the 28th (Fri) to allow time to drive to Rockland.

Things to do in Ogunquit

Parks Outdoors Beaches

Side Trips

Portland, Wells, York, Kennebunkport, York Beach
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Perkins Cove ©
Perkins Cove
Ogunquit Beach ©
Ogunquit Beach

10
nights
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Get outdoors at Mount Battie and Ducktrap River Park. Do some cultural sightseeing at Cellardoor Winery and Farnsworth Art Museum. Explore the numerous day-trip ideas around Rockland: Waterville (Colby College Museum of Art & Two Cent Bridge), Lake St. George State Park (in Liberty) and Fort Point Lighthouse (in Stockton Springs). There's still lots to do: immerse yourself in nature at Camden Hills State Park, experience rural life at Aldermere Farms, visit a coastal fixture at Owls Head Lighthouse, and tour the pleasant surroundings at Pitcher Pond.

To see where to stay, more things to do, maps, and other tourist information, go to the Rockland trip planner .

You can drive from Ogunquit to Rockland in 2.5 hours. Alternatively, you can do a combination of train and bus. Traveling from Ogunquit in September, expect nights in Rockland to be about the same, around 12°C, while days are slightly colder, around 24°C. Wrap up your sightseeing on the 8th (Mon) early enough to travel to Lubec.

Things to do in Rockland

Parks Nature Museums

Side Trips

Camden, Owls Head, Belfast, Lincolnville, Waterville
Highlights from your plan
Farnsworth Art Museum ©
Farnsworth Art Museum
Mount Battie ©
Mount Battie
Cellardoor Winery ©
Cellardoor Winery

9
nights
Lubec

Lubec ©
Lubec is a town in Washington County, Maine, United States. Step out of the city life by going to Quoddy Head State Park and Roque Bluffs State Park. Change things up with these side-trips from Lubec: Pocomoonshine Lake (in Baileyville), Eastport (The Commons Eastport, Eastport Fabric Emporium, & more) and Jasper Beach (in Machiasport). There's much more to do: visit a coastal fixture at West Quoddy Head Light, explore and take pictures at Saint Croix Island International Historic Site, examine the collection at Burnham Tavern, and tour the pleasant surroundings at Reversing Falls Park.

To find where to stay, more things to do, other places to visit, and tourist information, you can read our Lubec trip planner .

Traveling by car from Rockland to Lubec takes 3.5 hours. Expect a daytime high around 17°C in October, and nighttime lows around 6°C. On the 17th (Wed), you'll travel to Bar Harbor.

Things to do in Lubec

Parks Nature Wildlife

Side Trips

Eastport, Calais, Machias, Reversing Falls Park, Roque Bluffs State Park
Highlights from your plan
West Quoddy Head Light ©
West Quoddy Head Light
Quoddy Head State Park ©
Quoddy Head State Park
Jasper Beach ©
Jasper Beach

11
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Relax by the water at Sand Beach and Little Hunters Beach. Your cultural itinerary includes sights like The Seal Cove Auto Museum and Catherine Hill Winery. Step out of Bar Harbor to go to Winter Harbor and see Schoodic Point, which is approximately 1h 15 min away. Spend the 20th (Sat) exploring nature at Acadia National Park. Next up on the itinerary: head off the coast to Mount Desert Island, trek along Champlain Mountain & Beehive Loop Trail, identify plant and animal life at Shore Path, and contemplate the waterfront views at Jordan Pond Path Trailhead.

To find other places to visit, more things to do, where to stay, and tourist information, go to the Bar Harbor trip planner .

Drive from Lubec to Bar Harbor in 2.5 hours. In October, daytime highs in Bar Harbor are 17°C, while nighttime lows are 6°C. Cap off your sightseeing on the 28th (Sun) early enough to travel back home.

Things to do in Bar Harbor

Parks Outdoors Nature

Side Trips

Acadia National Park, Asticou Azalea Garden, Catherine Hill Winery, Schoodic Point, The Seal Cove Auto Museum
Highlights from your plan
Acadia National Park ©
Acadia National Park
Cadillac Mountain ©
Cadillac Mountain
Shore Path ©
Shore Path

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