there ARE ladies who will make the trip for certain minimum bookings...or you can engage a lady to travel with you.  it's well-known that the lower keys are a provider wasteland.

45 or 35 mph speed limits that are patrolled closely.  The drive takes me 4 hours at the minimum depending on time of day and day of the week.  Key West is a fun place, just not a lot of providers there.

I visit the Keys for an extended time every winter. I have never known of any consistent quality providers to be touring there.  
I agree and understand the drive from SF and therefore need a multi hour visit to do so. My struggle is finding the window of time and day that suits both schedules. Working on that.  
I am adding to my bucket, hoping I will make scheduling a priority.  
Get pretty laid back down there.

It is not a place that lends itself to "the hobby." Without writing a dissertation, 1) Generally, the hobby thrives in urban environments.  Despite high tourist traffic, the Keys are rural. Participation in the hobby requires a degree of anonymity difficult to consistently achieve in a rural environment. 2) Wrong demographics.  For example, generally, the snow birds are older, married and cheap, while the tourists are younger drunk and cheap.  3) Intense LEO presence with relatively little crime.  The Keys have more sheriffs, local police, immigration, FWC and Boarder Patrol per square inch than perhaps the White House.  

I could go on, but you get the picture?