I'd asked about renting a boat around Marathon or Key West and Gary Wall from SmarterSail replied, how'd you like to sail to Dinner Key? So it was a cruise/delivery deal. These guys have two sizes of Hunters. Then there is Bill Cooper's Pagan Fleet in Marathon, also smaller boats, and another fleet of larger boats, perhaps still at King Fisheries in Marathon. The woman at Pancho's fuel dock in Marathon said she didn't know anyone rented sailboats in the Keys!
We used the Cruising the Florida Keys by Young & Stinemetz a lot to plan anchorages and routes. Although we'd marked many locations before heading south, the actual stopping places were chosen on the fly, based on conditions and what we found.
It's not much like our home cruising grounds in New England. It's shallow (when it's not too shallow) and the routes are limited. The wind does blow all night; not making for restful anchorage in empty places. As the chart shows, we first went outside in the Hawk Channel which is rocking sailing and then cut inside where we mostly had to motor (and follow the charts!). We had two GPS's and the Richardson chart book on/open all the time. We had almost no bug problems, but gunkholing around the inside, north of Marathon to Key West, might find 'em. Lots of mangroves and wildlife and overall pretty devoid of other sailors.
It was a neat opportunity to spend boat time in a place we'd always wondered about. And of course escape the winter!