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Boothbay Harbor is not far from Boston, only roughly about 160 miles or three hours driving in good conditions. Flying into Boston and renting a car is definitely an option as the Boston Logan International Airport serves the world. There are many car rentals available from this airport as well for you to begin your journey northward to Boothbay Harbor. The following rental car companies are available at Boston Logan:
There is a slight problem with this strategy however; traffic in Boston is horrible and road construction can definitely slow your plans of taking off out of the city. Check the airport's website for construction updates and try to plan your trip around rush hour traffic as best as possible.
The closest airport to Boothbay is Portland International Airport about 65 miles away, it does have direct flights but not from everywhere so you really need to check the schedules carefull. Another option is the airport in Manchester, NH, a little closer than Boston and without the city traffic, and it is served by a major low cost carrier. Finally in Maine, Bangor International Airports is a few hours drive from the north which can be convenient if you want to visit Bar Harbor too. Although flying into these airports may cause an additional layover, the time saved on traffic could definitely be worth it.
When driving in Maine, diligently follow the speed limit as it is actively enforced.
Be sure to visit the Tourism Bureau for Maine's website as you may be able to request free maps and informational brochures.