There are so many hull forms, and pros/cons to each, that you will never be able to get a definitive answer here. I have my opinions, and there are those here who have their''s, and "never the twain shall meet". But here''s my two cents worth.
Ok, so you want to "Go to sea" in a sailing vessel, BRAVO! I am a strong proponent to cutting your teeth on a smaller (read 12-14 foot) dingy with a main and jib
. You will learn more quickly and more for the actual "feel" of sailing than in any other method, PERIOD. A used "Blue Jay" can be had for about 500 bucks and will teach you all you need for starters
. Sell it after a year, for the same 500 bucks, to another enthusiastic beginner and you will be keeping the sport alive. Also spend time sailing OPB (other people''s boats) as often as you can. Go to the local yacht club and post on the crew wanted/available board. You will learn TONS of stuff about sailing that would take the average cruiser years to learn, if they learn them at all. You will also be able to get an idea of what you might like in your future boat. So now you have learned on your dingy, and hustled around the racecourse for a year or two, and will have a great basis of information on which to go to the next level, finding your dream boat. If you are planning any extensive cruising, you are going to need at least 30 feet. It''s not about the size or speed or stuff like that, it''s about storage and seakindly motion. You need to have enough boat to take along the supplies you will need for extended time away from shore. And an overloaded small boat will be a horrible handfull in the nasty stuff. Not to mention the whole itimidation factor. A 10'' wave to a 20'' boat looks like a tsunami, but to a 35'' boat it looks like just another big roller.
With all that being said, spend some time looking on yachtworld using their advanced search feature. You can really narrow down the playing field there. You did not mention a budget, but you will be able to put one in there and search away. Go to the local marinas, the ones that seem to cater to sailors, and ask questions. Be polite, but ask an owner why he/she boght their boat, what are it''s strengths and weaknesses. You will be suprised at the number of folks who will ask you aboard to show off their pride and joy. Maybe even carry a little notebook to take down some realative facts. When you see something different on a boat, ask the owner why it is designed/rigged that way.
In you situation, you have nothing to lose and everything to gain by being inquisitive.
As a parting shot, take a look at an Allied Luders 33. Inexpensive, rugged, "honest" boats. Nothing fast or flashy, just a good old boat that will get you there and back with not much fanfare or trauma. Their motion might not be to some folks liking, and they might not be fast enough for others, but as a first cruiser, it makes a sound purchse that you will not lose you shirt on when it''s time to sell. Just keep in mind, that when buying an older boat, you will be faced with the daunting task of bringing her systems up to date, unless you are lucky enough to find one that has had a well documented history or care, maintenance, and upgrades (very rare, unfortunately)