I was at the Cayman Islands and stayed at the East end with the family (and four other couples) over Easter. I did not bring by gear... since the wind finders said there would be no wind. I wake up the first morning, and there are two guys riding right in front of where we were staying. After I spit my coffee all over my shirt and the pool, I sprinted to "the Kitehouse" (within walking distance of where I was staying), and the guys there got me set up with a "water taxi with gear" - 100 cayman dollars. They use the desk for the dive house, so there is always someone to talk to, give wind updates - much better than the "pray the call me back" situation at the Kitehouse in Key West. Anyway, the launch from our beach was in a wind shadow, so they took me out to a sandbar and had me riding on a new Cabrinha kite and board.
It was a blast riding around, looking at stingrays, butter smoooth water inside the reef, waving to the wife and kids, all afternoon. Most of the people with whom we were staying had never seen kiteboarding.. so it was fun showing off a little bit. When the wind dropped to about 13 knots, they loaned my a "plasma board", which was a great light wind board.
I rode another day that week, and went diving with the same outfit.
It was all perfect until my very last landing. As the only kiter left riding when everyone else was landed and packed away... I rode up to the instructor to ask him where he would like me to put the kite down - thinking I wanted to make it easy so everyone could get home. Imagine my shock when he threw a hissy fit since I was upwind of him (just a little). But... that's where the sandbar was! The water was deep in spots further downwind.. I swear! I got the full "riot act" read to me about how my kite was going to Hindenberg at any minute and I was going to wipe out him, his livelyhood, I was scaring the "sh#t" out of everyone in the boat, etc.. etc... Ouch!
Those guys can be pretty fussy... but I guess to them I am just another douc:e bag from the Midwest who might Hindenburg a kite at any given moment.. not a Maui Trained Kitemaster.
Other than that, it was a blast and the KiteHouse - Cayman - is a good resource, (if your ego can take it). Just clarify ahead of time exacty where and how they want to to land the kite by the boat, and maybe you can avoid a blistering tongue lashing like I got.