I'm a good but not great sailor and have 2-handed both 50' cats and keelboats around the BVIs multiple times. Some personal learnings for you:

1. Don't let the mainsheet foul itself around the propeller. Hilarity of the not so hilarious kind will ensue.

2. Don't let the drunken helmsman persuade you that the anemometer at the top of the mast needs repair and that you need to rig a bosun's chair to haul his drunk ass up to check on it right then.

3. You don't know how to set an anchor. No, you don't. You don't know how not to fry a windlass motor. No, really, you don't. Mooring balls - worth every nickel.

4. Why are you waiting until moored to start drinking? This is the only, only time when you can drink and drive and NOT be an appreciably greater menace to society than you already are on that big chevy suburban of a cat.

5. You don't, for fuck's sake, need to visit the Willy T. Yum. Conch critters and cougars at the Willy T.