Join Date: Feb 2006
Location: Florida, US northeast
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Most points have been made in earlier posts but here's my 2 cents.
First, a big boat is probably the worst way to learn. In many ways they are more forgiving and you won't notice things, like trim and crew placement, that would make a difference in a small boat. It's not for nothing that many of the great big boat sailors, like Buddy Melges, are graduates of small boat racing. In things like docking, of course, big really can really cause problems. You need some experience then.
Second, once you learn to sail, you can probably single hand a boat that's bigger than you want. I met a guy in Saugatuck, Michigan who was single handing a 62 footer. The real question is how big a boat do you need. Then that decision gets complicated and requires some knowledge. I sailed my Pearson 30 alone for many years with no difficulty, even before I bought an autopilot. It was the perfect boat for what I was doing, which was day sailing and weekending. For extended cruising it was just too small for me, although I did live aboard for a while. When my wife and I went cruising for part of every year it was too much like camping, so we bought a bigger boat, an Islander Freeport 41. With the ketch rig, she's no harder to sail than the Pearson. The sails are about the same size and we have roller furling on the jib. An electric windlass takes the strain out of handling the anchor. There's plenty of room and, to tell the truth, she's probably a bit too big. Complexity and maintenance increase exponentially with size. Dockage costs more. Bigger is better, up to a point. Then it's just an un-necessary expense.
Good luck and best regards,