Come on down to Buzzards Bay. There's a lot of great places to go from Buzzards Bay, including the Elizabeth Islands, Cuttyhunk (which is one of them), Martha's Vineyard, Nantucket, Block Island, Newport, just to name a few places that you can easily get to from Buzzards Bay.
USCG documentation is fairly inexpensive, and very easy to do if the boat was USCG documented previously. It is easy to do if the boat was only titled previously. The costs are less than $200 IIRC, and they are a ONE TIME ONLY cost...
not paid annually as required with state registration and titling. An additional benefit, at least in Massachusetts is you don't have to have the ugly sticker and bow numbers on your boat.
Other benefits included uSCG documentation provides additional privileges when travelling in foreign waters, which may not recognize state registration. So, if you want to go down to the Bahamas or up to Canada, that becomes a bit simpler
The catch is that the boat has to be owned by a US citizen.
My research in where to put the boat in the water (when it's ready to) nudges me towards Salem; moorings can be purchased outright rather inexpensively, comparing to renting one from a marina or club. Renting a slip is way too expensive for us, even for just a 27 foot boat.
At the moment, the boat is by Buzzards Bay. I've looked from Portland, ME down to Boston and Salem seems to have a couple mooring possibilities that are affordable. It's ~90 minutes from us, which is about what it'd take to get to Portsmouth, Hampton, or Newburyport too and not as far out on Cape Ann as say, Gloucester. On the other hand, pending finding out prices for a boatyard and transportation and what not, we may end up just staying where we are; it's about a 2 hour drive.
Anyhoo, that's a long way of saying we will 99.9% of the time be in Mass. waters. So I know I'll have to register the boat there. I am just surprised as not having to have a title for the boat in NH; seems the easiest way to prove ownership. I guess the other documentation will serve.
And no, I hadn't considered documenting. I'm not famliar with the process. What are the pros/cons? (she said, making a note to google it)