A lot of years ago Rick and I tried to get a group together to sail across the backcountry from Blackwater Sound to Flamingo. Nobody else wanted to do it, so we did it ourselves on our Hobie 18. It was one of the most fun things I have ever done. I wrote an article about it that was in the Hobie Hotline. But that was another case where you had to do some serious navigating and paddling and sometimes get off and tow or push.
In places the bottom is like pancake batter! If you jump off you'll sink in up to your waist.
For those interested, I sailed the Tiki (14"draft) from Flamingo to Tavernier. My course was via Dump Keys and Billy Channel, through "toilet seat pass" to the Conch On Inn, which is right on U.S. 1.
