I completely concur... you will not get enough use in the Keys to
justify it, and you will be hating life because of all the additional
crap you have to deal with as a result.

Imagine, you and your family receive your luggage and gear on the
other end. As prudence would dictate, before you even leave the
baggage claim, you check the board for dings, battens for breakage,
etc. If you are lucky enough to find none - a major miracle and
probable world first -then you avoid having to deal with
unsympathetic baggage services, who could care less about the
integrity of your gear.

You then schlep your stuff out of baggage claim and get your car.
Don't tell them about the boards, or they will tag you for a full
cavity search when you return the car. You see, they know about this
sort of stuff. Then what? Onto the shuttle with all the gear, to
get the car (unless Miami has changed something recently...). Good
luck... Or leave it and your family at the terminal with the gear
while you go get the car and come back... hmmm. not so attractive,
that, eh.

Now you've got the car and are reunited with your family. So you try
to figure out how to get the "soft rack" you bought strapped on the
car, which is not the type/class/model that the rental company told
you was available (BTW, soft racks ALWAYS fubar the paint or bodywork
somehow, no matter how careful you are...) By now, you've blown a
goodly portion of your travel day away with stressful crap, and you
still need to drive a long way down the Keys, and get to the beach...
and then maybe there is no wind. Or only one or two days of it. And
then you get to do it all in reverse on the way back...

Nope, do yourself, your family, and your vacation in general a HUGE
favor and plan on renting. Unless you are going somewhere that you
KNOW it will blow more than 60% of the time, or unless you are going
for a vacation measureed in months, just take your harnesses and
wetsuits, and relax.

By the way, getting used to rental gear will actually improve your
sailing (especially if it is state of the art gear), since it causes
you to concentrate on what you're doing differently, rather than
running on autopilot like you might with your own stuff.

If you are still considering it, it sounds to me like you would need
a board bag (at least 1/2" foam, and more stuffed in around the board
so it can't slide in the bag... towels work well for that), a soft
rack (glorified straps with clips into the door frame pads that sit
on the roof in direct contact with the paint... not good, but then it
is a dental, right), mast/sail/boom bag (unless you can fit them in
your board bag or don't mind gambling). By the time you get all
that, you will probably have 9 days worth of rentals all covered,
cost wise.

Best of luck either way... let us know how it works out. Especially
on the conditions you find. Haven't been to the Keys since I was a
kid, but I'm thinking of going back sometime... Driving all the way
with my gear on the roof probably. Because I am also a bit of a
masochist...

See you,

Greg