New perspective here. That would be a great NE downwinder from Matheson to either Blackpoint Marina (10 miles) or to Bayfront (15 miles).
Black point could be the mark and Bayfront could be the backup. I say that because if you miss Bayfront and cant get back up wind your pretty much SOL.
On that leg from Matheson to Blackpoint there are plenty of outs. I got a cell phone, waterproof pack, Garmin handheld GPS, and VHF if anyone wants to do a little experiment with me. I wont do it alone but Im game if I got company. PM me or give me a shout on the SE Florida forum. Im usually a Crandon/Marathon rider these days.
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