Are the flights cheap enough to cover the overpriced dockage in Key West?
Caloosa Cove Marina on the Atlantic side. Lower Matecumbe, South End of Islamorada (in my opinion) is the best deal in the Keys. $15 a foot per month (plus electric) including cable! Better yet, you can use the resort pool and tennis courts. Mostly 35-45 ft slips. Only 3 53/60ft slips. Directly on the Atlantic. Dry Stack Marina, Restaurant, Grocery, Bar, Diesel Fuel, Ethanol free gas, and Tru-Value hardware store all on premises. Also, if you have additional guests, the attached timeshare resort will rent out unoccupied units for $125 a night to boat owners who dock there. I think it's the best kept secret in the Keys. Way nicer than Plantation Harbor. My 58 Hatteras was a tight squeeze at high tide only, but what a great little spot once you're in there. The ONLY negative about this place, aside from shallow water, was that shopping in Marathon or Key Largo is still a 30 minute drive in either direction. It's a one hour, 30 minute drive from Miami Airport. Or Another hour and 30 minute drive to get to Key West. Stuck in the middle.
Where I am, in Palm Beach County, (30 minutes north of Ft. Lauderdale), (3 major airports), Some good dockage can still be had for $12-$15 a foot per month plus electric. These days, that still a fair price for dockage in South Florida. It's still the only place in America where you can "enjoy" boating in January! I heard of a couple of places up in the Stuart area for $9. The marina I'm at still only charges $1 a ft per night for transients.
I hope that helps.
Pizzaz's Daddy