are you planning on renting a room, or sleeping on the boat?
The biggest problem will be what to do with the truck and trailer. most ramps don't allow overnight storage of the towing rig... (and most ramps are shallow, set up for skiffs).
Grassy Key Marina, was one place I check out a few years ago, that was trailer sailor friendly.
Sea Bird maina on long key was another -both good sailboat ramps.
Gilberts in north key largo, or the south dade marina would be other good ramps. (but never been in south dade marina).
if you don't need access to the truck, you may want to launch in homestead, move the truck to a KOA, and head south. when you want the truck, get a bus to homestead then a taxi to the KOA.
there were a few other motels with good ramps I looked at, but its been a little while.
finally, recognize getting from ocean side to bay side is not easy in the keys... only a few bridges where you don't need to drop the mast, or have openings... (and the current is STRONG in the cuts).
Hawks cay is very nice resort, but you'll want a high tide to get the boat out. (ramp is shallow IMO). -also its a long way to bay side from there....
ps: -cold fronts are stronger on bay side in winter... (SW- NW winds)
