Take this apart however you like... it gets alot of mileage here in /r/sailing...

Here's my advice... (My own re-post) Want to sail for FREE? Here's how... You check your local sailing mag for race days in your area (Here in SF we have Latitude 38, brilliant rag...). Dress in layers and go down to your Marina/Yacht Club with a cardboard sign that reads, "RAILMEAT FOR HIRE" or "WILL SAIL FOR FOOD"... seriously, I mean this... This is literally how I got into the sport and I've had a blast ever since... See, these guys that get the big boats NEED people to run them. It's a challenge racing a 40ftr. single handed! Even if you're a Noob we always need weight on the rail, makes the boat go faster! Be honest with your Skipper about how much experience you have in sailing and he'll put you in the right spot on board. My first few times out I was the Beer Man / Rail Meat... still had the time of my life. As a beginner you need to listen to all the more experienced sailors on board, don't be afraid to ask stupid questions, learn to tie a bowline and above all... DON'T FALL OFF THE BOAT! Also try to have a thick skin as some Skippers can be rather loud when giving orders. Don't take it personal, it is what it is... If you find yourself getting seasick do not be afraid or embarrassed to hurl, we've ALL done it and you usually feel tons better afterward. I cannot stress the importance of a PFD. That would probably be the most costly part of your gear for right now (a good one is around $120 - $150) but it is a MUST HAVE and you need to get in the habit of wearing it ALL THE TIME. Sea water is really cold and wet clothes are really heavy, not good for your health at all. I've got more tips but not enough time for now... Best of luck to you!!