Rigging something forward of the tramp/mast/fwd crossbar is fine if it's kept small, light, and close to the forward crossbar for trim reasons (more on that in my response to your other post).
I don't know anything about the Keys, but I'd highly recommend spending a month or two learning the in's and out's of catamaran sailing before going on such an adventure. Maybe adventure on local lakes and in the gulf on a calm day, remaining close to shore and other boaters who can help you out in a jam. I wouldn't go on an offshore adventure without being very comfortable with the boat and confident in my ability to sail her, and especially how to right the boat in a capsize. It's not terribly difficult to capsize on accident, and if you can't right the boat, it could be extremely dangerous. Note that any addition or modification for carrying supplies could make righting more difficult and lead to "turtling" the boat, which is much more difficult to recover from. Anything you bring along should be waterproofed, as there isn't a place on the boat (not even inside the hull ports) where things won't get wet. For an "offshore" adventure, you'll want at a minimum a hand powered bilge pump, oar, VHF radio, and preferably a friend on a powerboat or jet ski that can shadow you or come looking for you if you don't make it to your intended destination after a reasonable amount of time. Let someone know where you're going and when you expect to make it there, and make sure they can go looking for you if you don't show up. Or find another Hobie sailor and sail together, so you can both watch out for each other! It'd also help to be somewhat familiar with the area and the local weather patterns, so you can plan whether you'll be primarily upwind, downwind or reaching enroute to your destination, where the shoals are that might tear off rudders & transoms or damage daggerboards and wells, or the places to avoid out of safety concerns, as fusioneng mentioned.
This may all be fairly obvious, but I suppose my whole point is just to make sure you have the skills for such a trip before leaping into it. Catamarans do handle somewhat differently from monohulls and dinghy's. The fundamentals are the same, but there are tricks of the trade when it comes to tacking, jibing, downwind sailing, etc. I'd recommend picking up "Catamaran Racing for the 90's," as I learned a lot about how to be more proficient at sailing my H18!
_________________ Mike '79 H18 standard ' Rocketman II' sail #14921 RIP '78 H18 ( unnamed) sail #14921'08 H16 sail #114312'97 H21SC sail #238
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