Max length = 26 feet

[Ishmael]

Here's my dilemma: I once had an ASA Bareboat rating (over 20 years ago), but haven't done much sailing since because my wife just isn't into it (she gets motion sickness in the car). When we were young, she indulged me and we bought a 1978 O'Day 27 and I had a mooring that would accommodate it. But...life gets in the way...built a house, a family and a business; sold the boat and gave up the mooring. I now have a mooring that limits me to a 26 foot vessel, and I now have a 17' O'Day Daysailer III that I use whenever I can find the time. I'm on the waiting list for a new mooring for a larger boat (it'll be several years before my number comes up). A seasonal rental mooring for a boat in the 27' to 37' range would cost me about $4,000 - not gonna do it. (My town mooring is only about $150/season).

I'd like to get a new boat that will give me the option for overnight and coastal cruising from my homeport (Nantucket), and also for summer live-aboard in the harbor. In that regard, the Nonsuch 26 is extremely attractive ("Classic" layout rather than the "Ultra" because of the 4 individual berths - and $). But my long-term goal is to work out the rust and get more proficient again in all things boating so that I may eventually "retire" to a boat (I'm now 48). Realistically, I'll probably never venture much beyond the Caribbean (snowbird - Nantucket for shoulder seasons and summer / Bahamas for the winters). But I don't see myself making the migration in a catboat - especially one that's only 26 feet. Eventually I would like to get a larger sloop/cutter.

So...should I go with the Nonsuch, or should I just get a sloop (26' or less) that will allow me to improve my sail-handling skills? Currently, I'm really liking the Ericson 26, but it's definitely more of a "camping" experience than the Nonsuch would be. I'd also like to keep the price for a new boat under $30,000.

This is a question I've been struggling with for a couple of seasons now, and I just can't seem to come to a decision. Any thoughts? I like the Nonsuch for the live-ability and comfort, but I don't think it'll really prepare me for the next boat after this one (or will it?)