6 days in Portland, Boothbay Harbor Region & Freeport Itinerary

6 days in Portland, Boothbay Harbor Region & Freeport Itinerary

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Route & dates

6 days in Portland, Boothbay Harbor Region & Freeport Itinerary

Start: Washington DC
Fly:  4​h
1
Portland
— Few hours
Drive:  1​h 30​min
2
Boothbay Harbor
— 4 nights
Drive:  1​h
3
Freeport
— Few hours
Drive:  30​min
4
Portland
— 1 day
Fly:  4​h
End: Washington DC

few
hours
Portland

Portland ©
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.
Shipyard Brewing Company has been added to your itinerary.

You can plan Portland trip in no time by asking Inspirock to help create your itinerary.

Washington DC to Portland is an approximately 4-hour flight. You can also do a combination of train and flight; or drive. Plan for slightly colder temperatures traveling from Washington DC in September, with highs in Portland at 73°F and lows at 52°F. Cap off your sightseeing on the 12th (Thu) early enough to go by car to Boothbay Harbor.

Things to do in Portland

Breweries & Distilleries
Highlights from your plan
Shipyard Brewing Company ©
Shipyard Brewing Company

4
nights
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. Your list of things to see and do now includes Cap'n Fish's Whale Watch, Damariscove Island, Tidal Transit Kayak, and other attractions. Step out of Boothbay Harbor to go to Bath and see Maine Maritime Museum, which is approximately 42 minutes away. There's more to do: identify plant and animal life at Boothbay Region Land Trust.

To see photos, traveler tips, and other tourist information, use the Boothbay Harbor trip maker .

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. In September in Boothbay Harbor, expect temperatures between 73°F during the day and 51°F at night. Finish your sightseeing early on the 16th (Mon) so you can drive to Freeport.

Things to do in Boothbay Harbor

Historic Sites Parks Wildlife

Side Trips

Maine Maritime Museum, Monhegan Light
Highlights from your plan
Boothbay Region Land Trust ©
Boothbay Region Land Trust
Cap'n Fish's Whale Watch ©
Cap'n Fish's Whale Watch
Tidal Transit Kayak ©
Tidal Transit Kayak

few
hours
Freeport

Freeport ©
Freeport is a town in Cumberland County, Maine, United States. To see more things to do, other places to visit, ratings, and other tourist information, read our Freeport planning app .

Traveling by car from Boothbay Harbor to Freeport takes an hour. Alternatively, you can do a combination of taxi and bus. September in Freeport sees daily highs of 72°F and lows of 50°F at night. Wrap up your sightseeing by early afternoon on the 16th (Mon) to allow enough time to drive to Portland.

Things to do in Freeport

Nature Parks Shopping
Highlights from your plan
Wolfe's Neck Woods State Park ©
Wolfe's Neck Woods State Park

1
day
Portland

Portland ©
Your day-by-day itinerary now includes Maine Narrow Gauge Railroad Company and Museum. Start off your visit on the 16th (Mon): examine the collection at Maine Narrow Gauge Railroad Company and Museum.

To see photos, ratings, maps, and tourist information, you can read our Portland trip planner.

Portland is just a short distance from Freeport. Finish your sightseeing early on the 16th (Mon) to allow enough time to travel back home.

Things to do in Portland

Museums
Highlights from your plan