9 days in Maine & Boston Itinerary

9 days in Maine & Boston Itinerary

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Route & dates

9 days in Maine & Boston Itinerary

Start: La Crosse
+3
Fly + Foot + Bus + Taxi:  8​h
1
York
— 1 night
Drive:  2​h
2
Boothbay Harbor
— 1 night
Drive:  1​h 15​min
3
Rockland
— 1 night
Drive:  2​h 15​min
4
Bar Harbor, Mount Desert Island
— 2 nights
Fly:  4​h 15​min
5
Boston
— 3 nights
Fly:  6​h 45​min
End: La Crosse

1
night
York

York ©
York is a town in York County, Maine, United States, near the southern tip of the state. On the 1st (Mon), examine the collection at Seashore Trolley Museum.

To find other places to visit, where to stay, ratings, and more tourist information, read York trip planner.

La Crosse to York is an approximately 8-hour combination of flight, bus, and taxi. You can also drive; or do a combination of train, bus, and taxi. Due to the time zone difference, you'll lose 1 hour traveling from La Crosse to York. Expect a daytime high around 62°F in October, and nighttime lows around 44°F. Finish your sightseeing early on the 2nd (Tue) so you can drive to Boothbay Harbor.

Things to do in York

Parks Outdoors Beaches

Side Trips

Footbridge Beach, Seashore Trolley Museum
Highlights from your plan
Seashore Trolley Museum ©
Seashore Trolley Museum
Mount Agamenticus ©
Mount Agamenticus
Stonewall Kitchen ©
Stonewall Kitchen

1
night
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. On the 3rd (Wed), take an in-depth tour of Boothbay Railway Village, look for all kinds of wild species at Boothbay Region Land Trust, and then visit a coastal fixture at Burnt Island Lighthouse.

To find maps, more things to do, other places to visit, and other tourist information, go to the Boothbay Harbor travel route builder tool .

Drive from York to Boothbay Harbor in 2 hours. Alternatively, you can do a combination of taxi and train; or do a combination of taxi and bus. In October in Boothbay Harbor, expect temperatures between 61°F during the day and 41°F at night. Finish your sightseeing early on the 3rd (Wed) so you can drive to Rockland.

Things to do in Boothbay Harbor

Parks Wildlife Museums

Side Trip

Boothbay Railway Village
Highlights from your plan
Boothbay Railway Village ©
Boothbay Railway Village
Boothbay Region Land Trust ©
Boothbay Region Land Trust
Burnt Island Lighthouse ©
Burnt Island Lighthouse

1
night
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. On the 4th (Thu), visit a coastal fixture at Maine Lighthouse Museum, then visit a coastal fixture at Owls Head Lighthouse, then see the interesting displays at Owls Head Transportation Museum, and finally do a tasting at Cellardoor Winery.

For photos, ratings, other places to visit, and more tourist information, refer to the Rockland route site .

Getting from Boothbay Harbor to Rockland by car takes about 1.5 hours. Other options: do a combination of taxi and bus. In October, plan for daily highs up to 58°F, and evening lows to 42°F. Finish your sightseeing early on the 4th (Thu) to allow enough time to drive to Bar Harbor.

Things to do in Rockland

Museums Historic Sites Wineries

Side Trips

Owls Head, Cellardoor Winery
Highlights from your plan
Maine Lighthouse Museum ©
Maine Lighthouse Museum
Owls Head Transportation Museum ©
Owls Head Transportation Museum
Owls Head Lighthouse ©
Owls Head Lighthouse

2
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 5th (Fri): hike along Bar Island Trails, then get a dose of the wild on a nature and wildlife tour, and then enjoy the sea views from Egg Rock Light. Get ready for a full day of sightseeing on the next day: contemplate the waterfront views at Eagle Lake Acadia National Park and then do a tasting at Bar Harbor Cellars Winery.

For photos, reviews, ratings, and tourist information, you can read our Bar Harbor day trip tool .

Drive from Rockland to Bar Harbor in 2.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 59°F, and evening lows to 42°F. Wrap up your sightseeing on the 6th (Sat) early enough to drive back home.

Things to do in Bar Harbor

Outdoors Parks Wildlife
Highlights from your plan
Bar Island Trails ©
Bar Island Trails
Eagle Lake Acadia National Park ©
Eagle Lake Acadia National Park
Egg Rock Light ©
Egg Rock Light

3
nights
Boston

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Freedom Trail has been added to your itinerary. Kick off your visit on the 7th (Sun): appreciate the extensive heritage of Freedom Trail, then take an in-depth tour of Plimoth Plantation, and then steep yourself in history at Mayflower II. On the next day, kick back and relax at Good Harbor Beach and then get interesting insight from Tours.

To find maps, traveler tips, photos, and other tourist information, you can read our Boston road trip site .

Traveling by combination of bus and flight from Bar Harbor to Boston takes 4.5 hours. Alternatively, you can drive; or take a bus. Expect somewhat warmer evenings in Boston when traveling from Bar Harbor in October, with lows around 50°F. On the 9th (Tue), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Boston

Outdoors Historic Sites Museums

Side Trips

Gloucester, Plymouth, The House of the Seven Gables
Highlights from your plan
Dolphin & Whale Watching
Good Harbor Beach ©
Good Harbor Beach
Freedom Trail ©
Freedom Trail

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