smaller distance stuff around here includes (name and approx. distance in miles):
Miami-Key Largo 50
Ft. Lauderdale - Key West 100
any of the various Cuba iterations 100
Steeplechase 100
Hiram's Haul 50
Florida 300
The current iteration of the Hogsbreath 100

I believe most of these are part of the Endurance Series?

Don't know dates for most of them (yet).

I had suggested a Naples - Long Key sail with overnight @ Everglades City or "expedition style" with no stopover as a feeder to Steeplechase and/or an experience builder for Everglades Challenge... but don't know if there would be enough sailors to justify the effort.

Plus, you'd have to bring your own banjo and crocodile rifle. It's serious back-woods, no support, "we're the Fugawee" stuff. Jake's been through there - he knows.