We had an excellent time during our one week stay in Boothbay Harbor -- we judge a vacation successful by whether we start thinking about moving there, and this vacation was highly successful; my husband is now very motivated to buy a cottage and retire here (at least during the summers).
We stayed at Harborfields and the accommodations, while rustic, suited our needs perfectly. If you're looking for luxury, this place is not it. But it's on the waterfront and our kids adored the dock and swam off it almost every day. They made lots of friends with the other kids staying at the other cottages, and spent many hours playing and swimming and rowing in the Harborfields rowboat. We stayed in the Wharf cottage, which is right over the shoreline and has a new deck that gave us stunning sunrises (close the curtains before bed if you don't want to be up at 6 a.m.) One quibble: the window screens were essentially useless; a bug could drive a mosquito-sized Mack truck through the gaps. This made it impossible to read in bed after dark, or even use a computer or other electronic device, as the bugs descended quickly. We didn't really mind going to bed at 9 every night, but it could be an issue for some. Oh -- bug repellent is critically necessary, as Maine has vicious predator bugs that make the bugs of our state (Pennsylvania) look like pikers. :)
We visited Reid and Popham state park beaches and found them both delightful and well worth the trip. Go to Popham at low tide to walk out to the island. There is a memorial marker at the highest point on the island, dedicated to a young man who apparently drowned there; I would love to know that story if anyone can chime in. We were a bit disappointed that we had to pay admission at each park (it was about $15 at each park - can't remember exactly) and couldn't buy some kind of day pass that would cover us at both. Of course, few people like to drive as much as we do, and aren't likely to try for both beaches in a single day. We were just having fun roaming. There is a weekly pass (?) but by the time we figured this out, it was not cost-effective.
We went to Pemaquid lighthouse at sunset. The time to visit this lighthouse, for photography purposes, is really sunrise. But that would have meant getting up at 4... The lighthouse is gorgeous and the kids loved exploring the rocky outcroppings. Definitely worth the drive; there is a fee to enter, but not, apparently, at sunset. The lighthouse was closed then anyway.
Another high point was Barrett Park. This is a municipal park, just around the corner from the landmark Catholic church in downtown Boothbay Harbor. We spent a couple of afternoons there, kayaking and swimming and picnicking. Great little sandy beach (rare) that was very close to us, and a lovely park with tables and bathrooms and shade and there was even a swing that had been roped on a tree. We loved this place - and no fee. The tide has about an 8-foot change, so low tide and high tide are completely different experiences.
I think our kids (and I) had the best time of the week at Monkey C, Monkey Do -- it's on U.S. 1 in Wiscasset. It was $99 for two hours of rope/zip line/tree top adventure. We all had a blast, except our 7-year-old, who got scared at about the second level. This is highly recommended if you're at all active. No need to be in great shape (I'm not, not by any means.) -- but if you're very overweight, you might not have a good time. I watched two overweight people getting winched down during our time there. That said, I was amazed at how much fun I had at this place. It was definitely worth the money.
We went on the Bay Lady, an old 32-foot sailing ketch (sloop?), that cost around $80 for two adults, two kids. Nice trip in the harbor and we sailed the entire time, which is what we wanted. That was the only real money we spent on Boothbay Harbor tourism activities. We just didn't have the budget for multiple excursions. The downtown is very quaint, riddled with precious shops, which aren't really our cup of tea. But we enjoyed walking around, and our English mastiff was marveled over by everyone. (Yes, Harborfields accepts pets, for an extra $75).
We had breakfast at Mama D's and really enjoyed the backyard deck. Waffles were excellent. They only take cash, though, so be prepared.
The only sour note was Red's. We drove there our first night for lobster rolls. Ordered four rolls, plus fries, plus four drinks. Total was $92 and change. I just about fell over. There are restaurants in New York that cost less. And we don't have to swat bugs and eat in the dark (lights on their deck are off because of bugs, I guess). IMHO, the place is crazy overrated.
After that, we bought our own lobster every day at the docks and made our own lobster rolls. Lobsters were insanely cheap -- $4 for a soft-shell -- and it made no sense at all to pay the inflated restaurant prices. (My husband does all the cooking, so that influences my judgment a bit -- though I did do all the dishwashing, which is a lot harder than at home, with no dishwasher)
We did a day trip down to Brunswick to visit a friend and can highly, highly recommend Gelato Fiasco. I want to order their gelato online, but can't. It is available in some regional supermarkets, but none by me. This was an amazing treat. The gelato was quite inexpensive and they'll put as many flavors as you want in a single serving, plus they offer free samples, as many as you like, while you try to make up your mind. We even detoured there on our way home, just to get more - but they didn't open until 11 and that would've meant a two-hour wait, so we regretfully left. Boudin College has a museum devoted to arctic exploration, the Peary-MacMillan Arctic Museum, and there is also a William Wegman exhibit at the college's museum of art -- we enjoyed both of those, plus an outdoor performance of MacBeth. All free.
We had wanted to rent kayaks but the prices for the four of us made no sense - we could buy kayaks for what it would cost to rent them for a couple of days. So that's what we did - we drove to the Walmart in Brunswick and bought two inflatable kayaks and a car lighter-operated pump for $200. They were fine for paddling around the harbor, which was all we wanted. Not something for ocean kayaking, or long tours, but we have little kids so that wasn't in the cards anyway. And we could pack them and take them home easily, where we are now enjoying them on our creek. Win-win!
I think that just about covers it. Any questions, just ask.