Originally Posted by kilarney
I live in northern New England, and sail in lakes. Offshore sailing and large waves are not an issue - although I'd like to be able to occasionally use the boat in protected ocean bays or Long Island Sound...
I'm also starting to think that I should just go with a 25 foot weekender type boat, but's that a thread for another day. The biggest problem with going up to that size is the lack of late model used boats and the fixed costs associated with a boat that is not routinely trailered...
Here is a book with some 360 boats to choose from to 25 feet: The Sailor's Book of Small Crusing Sailboats, by Steve Henkel. Take a look at chapters 11, 12 & 13 to help with the selection process.
There are ways to rig the boat while on the trailer that makes it easier.