8 days in Boston, Boothbay Harbor & Bar Harbor Itinerary

8 days in Boston, Boothbay Harbor & Bar Harbor Itinerary

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Route & dates

8 days in Boston, Boothbay Harbor & Bar Harbor Itinerary

Start: Milwaukee
Fly:  4​h 45​min
1
Boston
— Few hours
Drive:  3​h 15​min
2
Boothbay Harbor
— 3 nights
Drive:  3​h
3
Bar Harbor
— 4 nights
Fly:  4​h 15​min
End: Boston

few
hours
Boston

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.
Kick off your visit on the 21st (Fri): buy something for everyone on your list at Faneuil Hall Marketplace and then admire all the interesting features of Fenway Park.

To find reviews, maps, more things to do, and more tourist information, read our Boston trip builder website .

Milwaukee to Boston is an approximately 5-hour combination of flight and bus. You can also do a combination of bus and flight; or drive. You'll lose 1 hour traveling from Milwaukee to Boston due to the time zone difference. Expect a daytime high around 75°F in September, and nighttime lows around 59°F. Finish your sightseeing early on the 21st (Fri) to allow enough time to drive to Boothbay Harbor.

Things to do in Boston

Shopping
Highlights from your plan
Faneuil Hall Marketplace ©
Faneuil Hall Marketplace
Fenway Park ©
Fenway Park

3
nights
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. You've now added Cap'n Fish's Whale Watch to your itinerary. Kick off your visit on the 22nd (Sat): admire the natural beauty at Coastal Maine Botanical Gardens and then get up close to creatures of the deep with Cap'n Fish's Whale Watch. Get ready for a full day of sightseeing on the next day: cool off at Old Orchard Beach.

To find ratings, other places to visit, maps, and other tourist information, read Boothbay Harbor trip itinerary builder site .

Getting from Boston to Boothbay Harbor by car takes about 3.5 hours. Other options: do a combination of bus, flight, and taxi; or do a combination of bus and taxi. Expect slightly colder evenings in Boothbay Harbor when traveling from Boston in September, with lows around 51°F. Finish your sightseeing early on the 24th (Mon) to allow enough time to drive to Bar Harbor.

Things to do in Boothbay Harbor

Parks Outdoors Beaches

Side Trips

Coastal Maine Botanical Gardens, Old Orchard Beach
Highlights from your plan
Old Orchard Beach ©
Old Orchard Beach
Cap'n Fish's Whale Watch ©
Cap'n Fish's Whale Watch
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens

4
nights
Bar Harbor

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Step out of the city life by going to Mount Desert Island and Cadillac Mountain. Shop till you drop at Fiore Artisan Olive Oils and Vinegars and A LITTLE MAD. Spend the 26th (Wed) exploring nature at Acadia National Park. There's lots more to do: look for all kinds of wild species at Shore Path, look for gifts at The Acadia Country Store, kick back and relax at Sand Beach, and get interesting insight from Tours.

To see maps, other places to visit, ratings, and more tourist information, refer to the Bar Harbor online trip builder .

You can drive from Boothbay Harbor to Bar Harbor in 3 hours. Other options are to do a combination of taxi and bus; or do a combination of taxi and bus. In September, daily temperatures in Bar Harbor can reach 70°F, while at night they dip to 52°F. You'll have a few hours on the 28th (Fri) to wrap things up before traveling home.

Things to do in Bar Harbor

Parks Nature Wildlife

Side Trip

Acadia National Park
Highlights from your plan
Acadia National Park ©
Acadia National Park
Cadillac Mountain ©
Cadillac Mountain
Shore Path ©
Shore Path

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