Originally Posted by Idiens
He said he wanted to go cruising, you are suggesting race training, which requires crew, crew, crew (or be-yelled-at, be-yelled-at, be-yelled-at - 'cos that's what they do to be fast and hard - and win. (Ian's got the best idea, meet some friendly sailing people first).
I'm saying "crew-crew-crew" for the most instructive and rapid way to acquire the real-life skills every cruiser needs, particularly for boat and sail handling. He can offer to crew for cruisers on the weekends or holidays, by honestly saying "I have crewed at these positions in these many races on these types of boat", and therefore let them decide whether he's going to be a help or a hindrance.
Same with racing captains: Pick one that lets you cycle through the five or six critical positions on a race boat: grinder, tailer, foredeck/bowman, helm, mainsheet, tactician and/or navigator. Sail as much as possible and, after a few races, in challenging conditions. This will ingrain good habits of seamanship and will allow you to get the most out of whatever boat you get, even if it's a not-particularly-weatherly tub.
I raced for five years and loved it without necessarily wanting to do it myself (except maybe for a "cruiser" type race). I feel now quite relaxed in most conditions...because I've been in most conditions
...(race skippers HATE to have a race called off due to heavy weather! They see 35 knots as "an opportunity", right, Giu?).
Racing has immensely enhanced my cruising, and made me notice that a lot of cruisers are strictly fair-weather (which is fine) and some who've had the same boat for years don't quite know how to sail them. That's fine, too...for fair-weather sailing.