We just went through our first boat hurricane prep (done enough in houses in the carib and Pacific) in the USVI. Luckily St. Thomas was spared the wrath of Dean, but the week leading up to it was tense. The boating community sure gets stressed during this time.
Some things I noticed:
The majority seem to wait until the last minute to do something. We are in the middle of storm season and the marine supply store sold tons of chain, shackles, etc. in the days before Dean. Thus, get on it early, have a plan A and B and the gear for it.
Many boats were never attended to... thus ready to become slow projectiles aimed at our boat.
Marina: We opted for an open slip in a protected mangrove lagoon. While it seemed like a good idea, it may have not worked with a Cat 3-5 storm as the pilings/docks were a wee bit shabby. Check your marina closely.
Get Off the Boat: In hurricane Marilyn (1995 VI), all of the deaths were of boaters on their boats. One guy who survived, was swept off his boat in Charlotte Amalie harbor (S side St. Thomas) and woke up on the beach on Jost Van Dyke (N of St. Thomas)... an 18 mile ride!! Concrete is our preferred bed for a storm.
Get the stuff off: Remember that you may end up with water down below... lots of it. And a cabin stuffed with sails, bimini, etc. all soaking wet is a nightmare to deal with. Ok, a soaked boat is a nightmare, but a soaking wet jib for a 40' boat can be a bear.
Mangroves: Wear serious footwear for the dance of tying to mangroves. One slip and you could be cut bad by barnacles and mangrove oysters. Plan on lots of lines to make it to healthy big branches. Plan on rats.
Many ways to go about it: There are as many ways to prep as there are old salts out there. And each is best in the right situation. Noting is perfect except getting your boat out of the belt during the season. OW, prep and hope the gear goes unused.
Fingers crossed for the rest of the season!