Originally Posted by Captain K
I'm discovering, contrary to popular notions and to my dismay, there's a dearth of good anchorages in the FL Keys.
In Key West there are few choices for a non local, and your satement has more truth for the lower 30 miles of the island chain than the upper 80.
Captain Papy's Cruising guide is my favorite,
Cruising Guide Florida Keys, Bahamas Cruising Guide, Frank Papy
and once you get above Newfound Harbor just below the 7 mile bridge there are a great many anchorages on the Bay Side of the chain. (Little Palm Island at the entrance to Newfound Harbor is where they filmed PT109)
Above Channel 5 at Lower Matecumbe just about anywhere on the Bayside is a good anchorage with some outstanding choices that are convenient to shopping and dining and outstanding sunsets.
The choices are fewer on the Hawks Channel side, but there are several like behind Tavernier and Rodriguez Keys.
In the summer when things are calm we overnight on the reef, sometimes for days when things are calm as the reef provides good protection from the prevailing E-SE winds.
For those not willing to venture into the Bay, there are much fewer choices but above the 7 mile bridge the ICW is bayside and well marked with plenty of draft.