I've been mulling this over, thought about asking in the Learn to Sail forum section, but I thought I'd ask here as more folks would likely have more personal experience to share.
I learned to sail on 16' Bullseyes when I was young, windsurfed a bit, and am getting myself back into it sailing Rainbows at a local school/club membership program. I was talking to a good friend who is eager to sail when he retires, and has decided on buying a 40'-ish multihull (in the $500k range, so he thinks) to take off on and sail the world, after doing some ASA courses.
So, you can guess where I fall on this, but I'm curious whether I'm totally off-base, and he's more sane than I think... I always figured it's best to start small, work your way up, beginning with boats where you can overcome mistakes a bit more easily, in smaller water with smaller forces involved, and work your way up to the big sailing. That all being said, here's what I'm wondering...
How did you all get from starting out from scratch to where you are now? What progression of boats did you sail/own/experience, as owner/skipper, as crew, and what do you think makes sense as a set of steps to take?
I'm enjoying the Rainbows now, and am remembering all manner of things I forgot, and working on singlehanding in relatively controlled, mellow conditions before looking to buy something next year. I was thinking something in the 25-foot range, to take the next step up, with the option to overnight with my small troupe (dog/wife/daughter), before moving up again a few years later to something around 30' for doing cruising down the coast here in the Northeast. Clearly, I like the concept of going small to big, but I know there are folks who've gone in at the deep end with a big boat, headed offshore and survived... I'd like to get into bluewater sailing eventually, shorthanded or singlehanded in all likelihood, but I'm figuring on taking my time to get there.
I know that on a smaller boat, I feel like when a mistake happens, you can more readily muscle your way through it... you can't body-english a 37' heavy displacement boat, but you can still hope to on a 2500 pound rainbow, it seems.
Any input is useful food for thought... what did you do, what would you recommend, what would you do differently, what do you think is ideal, what are you amazed you survived (