I have a few questions for you.
Are you sailing alone? Having a second person will help in higher winds, and help right the boat in a capsize.
Are you completely new to sailing? If so, I'd recommend taking a few lessons, or get someone experienced to teach you the basics. (Honolulu? I'm available! Just need to pay my plane fare from Chicago!

)
Are you a comfortable swimmer? Whether you are or not, always wear your pfd. Except for...just kidding...ALWAYS wear your pfd.
Do you have emergency equipment? You should have a marine radio (Cobra makes a waterproof, floating handheld) or a cell phone in a waterproof case ON YOUR PFD. You're on the ocean. It's big.
Also, you should have a couple flares and smoke flares in a waterproof bag on the boat.
When I sailed on Lake Michigan, an experienced friend insisted I get a marine radio and flares. Why, I said? My boat is small. Exactly, my friend said, and the lake is big. And the ocean is bigger. You don't want to be capsized with an offshore wind blowing your boat away faster than you can swim, with the tide going out, and no way to summon help.
OK, I know I sound like a downer. But sailing is an absolute blast! Have fun, get wet, dump the boat over, have lazy days, have scary days, but always come back to tell the stories!