[notfarnow]

One of the best tips made so far here: Crew on a boat. It's great if you know someone who races, but if not call a local club and say you're looking to crew. Most clubs have weekly races, and many boats are always looking for crew, and are very welcoming to strangers. No experience necessary, sometimes they want someone to work the winches or even just to act as "moveable ballast".


A few reasons to crew:
-If you sign up for weekly races, they generally go out in all weather conditions, so you learn to deal with a boat in less than ideal weather.
-Racing in particular offers a steep learning curve, you'll learn a lot about setting sails, reading the weather, rigging the boat etc... and you'll learn FAST, usually with a very enthusiastic bunch. It's almost the equivalent to being in the backseat at a DE!
-You'll be exposed to a lot of boats, and will quickly get a sense for what style, size and age suits you. Buying a boat can be expensive, and lots of folks go through 2-3 before they find a good "fit"
-Many boats are bought & sold at clubs without being advertised. You can buy with a little more confidence.

I sailed dinghies for years, and 3 years ago bought a Chrysler 22 trailerable sailboat. It was made in '73, and it is tough as nails... like someone else mentioned, a lot of the boats made before the oil crisis were very, very well built. Age isn't as important as condition.

Finding the right size is key:
-You want a boat that you won't feel cramped in, so you'll have to have a sense of how much time you'll really spend aboard. Overnight? Weekends? Weeks at a time?
-You don't want a boat that's so big you're not comfortable handing it alone. For me, a 22' boat has been ideal... I can rig it up in 10 minutes flat, so I can enjoy a 30 minute sail. However, now that my wife has started taking lessons, I'm starting to look at 26-30' boats.