Sloop, Cutter or Ketch
Jeff, I''d suggest you try to spend a day in your local waters with both cutter and ketch rigs. Pay particular attention to how each boat is rigged, as talking about ''ketches'' is like talking about ''cruising''; there are many differences between what one person refers to and another.
We prefer single masted boats and yet, twice, have ended up choosing ketches when planning and then executing Caribbean cruising ventures. In both cases, I''ve come to appreciate a lot of advantages to the ketch that may not appear prominently when the discussion is theoretical but become more meaningful when it''s just you, perhaps only one other crew, and you have to deal with a wide variety of conditions.
I disagree with Jeff H''s view that, on hulls that lack performance especially to windward, it''s preferable to pile a poor windward rig on top of it. And similarly, a good ketch rig (look at how Amels are set up) can keep a fast hull sailing pretty fast - even if not as wickedly windward-capable as a sloop. As two examples, a Mariner 36 and H-R Rasmus 35 were built as sloops and ketches and I think the ketch rig is highly preferable.
I don''t think ketches are the best choice; I don''t think there IS a best choice. In both our decisions, we were choosing a mix of things, including layout, build rep, price, flexibility in varying conditions (we were a man/wife crew of two), and of course what was available when we were shopping...and lots more. So rather than preach ''ketch'', I''d suggest you get more familiar, first hand, with each of these rigs so that IF the ''right'' boat shows up and is either cutter or ketch-rigged, you''ll be able to suitably weigh that rig into your overall decision-making.
BTW we most recently left for the Caribbean hoping we hadn''t jumped off the deep end and chosen too much boat (13M/42''). It was the ketch rig, especially in the heavy Xmas Trades, that made things so easy. As a result, we ended up crossing to Europe on this boat, feeling that the rig was one of the reasons this was okay. However, we did add an inner (Solent) stay for heavy wx. Unlike many, we chose to do the two long legs double-handed...and we''re no longer young at age 60. Our times were respectable for the conditions we found, and it was the rig that made day in/day out sailing a non-event.
Blowing hard, we sail on jib and mizzen. In light airs, we can add TWO light-air sails - an MPS and a mizzen staysail (a wonderful sail which I handle alone and yet is bigger than the mainsail). I wish our boat was better to windward; I really do. But this is due to very wide sheeting angles (beamy hull and wide shrouds), shallow-ish draft AND the rig. However, let''s keep things in perspective: cruising down to and in the Caribbean, people often find they are moving the boat 10% of their total time. Take away motoring into headwinds to get down there, and how often will you be sailing dead to windward? Perhaps a percent or two. The best reason to try and optimize windward performance IMO is for the pleasure it gives to sailing the boat. In real world applications, it''s just one of many factors.
Oh, and I didn''t mention the wind generator at the top of the mizzen, and the radar array, TV antenna and radar reflector all having a ''home'' a bit further down. No sailing purist will mention that, but boat owners/cruisers/liveaboards who have to install gear don''t overlook it.
Good luck on the search!
WHOOSH, now wintering in St. Kat''s, London