On Tue, 19 Aug 2008 21:20:07 -0500, Vic Smith
wrote:

There was a Carolina Skiff guy who did that trip - maybe multiple
times. Think he had a 20.' Flat water, and he was moving pretty
good. But he started on the mainland - Everglades City?

Just about any kind of trip like that is possible on the right day.
The fun starts when things start going wrong and cascade out of
control. What if you break down out there 50 miles from the mainland?
Your cell phone and VHF don't have enough range. If you can reach
another boat on the radio, and they can relay a message to SeaTow,
they might come out and get you - at a very steep price, probably in
the thousands. Free towing only goes 25 miles. USCG will do almost
anything to avoid coming out for you - you'll have to convince someone
that lives are at stake, and that's if you can get through to them at
all. The west coast of Florida south of Everglades City is 100 miles
of wilderness until you get to the Keys. Another interesting
consideration is that there are no supplies in the Tortugas or
anywhere else between there and Key West. Going from KW you need a
safe working range of at least 150 miles, from Everglades City more
like 250 miles.