Originally Posted by Hesper
I chose the opposite tack to what Drynoc proposes. After learning to sail, I took six years to learn how to sail well - mostly by racing with some of the best people I could find.
I did it back to front: I bought a 33 foot cruiser-racer, and then went racing as crew on a Newport 27 for five years, as did, to a lesser extent, my wife. Instead of watching our own halyards part and sails rip, we saw it on other boats, as racing (for better or for worse) tells you the limits of a boat and the limits of her crew.
We learned a great deal about heavy-weather tactics, laying the line, rapid tacks and where to find the puffs that would keep the boat creeping along when others were slatting and still.
We brought that knowledge to our own boat, which, while we didn't overload it, we kept pretty stripped out so that we could "camp" with an emphasis on sailing performance without the cost. This meant not obsessing over the state of the bottom, and having similarly sized used racing sails recut for our boat (a two-year old composite No. 1 for $200 is better than a 20-year-old Dacron No. 1 that's held together with patches!). Then, because we HAD the racing experience, we would push our good old boat a bit further and faster than typical cruisers, and we kept up the good race habits (ready about? Ready! Helms alee!, etc.) of helming and trimming in order to "cruise" in a way that got the most out of the boat. It has also encouraged us to drive the boat in big air, and in a blow, a normally packed cruising ground thins out very quickly after 18-20 knots or over a metre in wave height. To us, that's when the boat finally starts showing off!
So while I don't necessarily endorse getting a race boat as a first boat, I think if you get an OLD "cruiser/racer" like an Express or a Mirage or some other club/PHRF-type contender, you can then race on the "committed" race boats in your area or club, and this is the royal road to getting the most out of your old boat.
In my view, a lot of cruisers (not the majority, but quite a few) are happy to cruise about without trimming the sails or tensioning the stays more than barely adequately, because they've never raced and never learned much beyond the basics. This is a shame, because they frequently have boats that can work well to weather and can really lay down in some wind.