I agree...
...with both Michael and Mark that you should rent boats and it can become cost prohibitive. It depends on HOW much you will be sailing(renting). The typical breakover point is 6-7 three-day charters per year. If you charter this much or more, you are better off buying a vessel of appropriate size that will be less than the price of those charters. Lease programs work well for practice and skill improvement but you're just stuck with the same boat and if you don't like it, well, you've got a year to think about that. OTOH, you might be able to get into a fleet lease program where you can take out any of the fleet's boats with one lease contract/rate. This program is much harder to find though. I would also recommend chartering in different places to get a feel for what kind of weather, seastates, etc. you are going to enjoy sailing in. This is a large factor in deciding what is the best boat for you. the disadvantage of boat ownership is you have the same boat in the same place (unless you by a trailer sailor and can move it around a lot.) I like to sail lots of places and owning a boat limits HOW much you can spend on travelling to other places; but that's just my income....uh....opinion. If you do decide to rent/crew awhile and then dive into a boat, make sure it is something that is popular, used, and holds value well like the H240 H260 or C25 to give very few examples. Then if you decide to move up or change boats, you will get a good return on your money. Before you buy anything, check on insurance, slips, cost of fuel (usually negligable on a sailboat), and the cost of equipment you know you'll want. All big factors on how much to spend on a boat.I would still recommend taking some training. No, it will not make you an expert, but it will give you a good enough knowledge base to know what to try, what to practice, and what to do in emergencies. All of these are the toughest lessons to learn on your own. Plus, you should get good information on USCG Rules and Regulations, Rules of the Road, Navigation Aids, General Good Seamanship, and in some cases, American Red Cross First Aid and Adult CPR, all in the sailing class. Taking a class can eliminate a lot of frustration when you are out there trying to figure out what to do.Good luck!