Any time you pay more than $4k or $5k for a boat, or any time you buy a boat that you will routinely sail out of sight of land, you need to see a recent survey
report, even if it means paying the surveyor
yourself. And for a sailboat this is especially important. And not knowing what to look for, this is really super important. You don't want to be in "WHEEEEEE! THIS IS FUN!" mode, reaching across 30kt trade
the lee rail with all sails
pulling full and hard, and have your windward shrouds part or your chain plates pull out and your mast
goes kersplush and you start rolling violently and the mast
starts trying to pound its way into your cabin
, and you not knowing just exactly what it is you ought to be doing NOW.
Ideally, the deal is, you take care of the boat, and the boat takes care of you. As a newbie, it is mostly a little simpler than that... you don't know how to take care of the boat yet, but you trust the boat to take care of you. Which works surprisingly often and regularly, if the boat is up to the task. RIGGING
is critical. THROUGH-HULLS. RUDDER
and STEERING GEAR
. (Even a simple tiller can fall apart. Happened to me!) ENGINE
, PROP, and SHAFT. (including stuffing box) DECK/HULL JOINT. Then there is your electronics
and navigation equipment
. Safety equipment
. A surveyor
can keep you from buying a floating deathtrap for newbies. Even a well-found boat can kill you if you really work at being wrong, but a bad boat will do it quicker and more reliably. Don't buy a boat to go a-voyaging in, without a survey.
The thing about the Caribbean
is most of the time you have plenty of wind
. PLENTY. As in sometimes way too much for some boats. On unprotected passages, when the Trades are blowing strong, a small boat gets kicked around a lot. However, those passages are pretty short so you get a break when you anchor
for a day or three. All in all, I would not even consider anything smaller than 27' and over 30' would be better. As a beginner you should stick to a sloop
rig and a hull
under 40' just to make the obligatory arbitrary pronouncement and start the obligatory distracting argument. Keep it simple.
If you are just winging it on your own, first of all make sure you have all your required safety equipment
and are proficcient in its use. Second, get a few weeks inshore cruising in, before venturing outside. Make contacts with locals and learn from them. See Black Oak's thread on the trip to Bermuda
. That's how it's done. He started out with zero knowledge or experience, just a pocket full of money, and bought a boat and instead of wondering what to do next, he went sailing. Okay, that part wasn't too smart. But from there, he made friends and presented the good side of his personality and other yachties naturally were inclined to teach and help him, and now he is sailing around, only a few weeks later, more or less a competent coastal cruiser, well on his way to being ready to tackle Bermuda
. Another good reason to read that thread is to understand the combination of fear, uncertainty, and frustration you will experience as part of the self-learning process.