Naples, Naples - gateway to the 10,000 islands and a 40 minute drive from Chockaloskee; gateway to the Everglades.
I ahve fished with Dave Cassady (email@example.com) 941-352-7292 twice; once in the 10,000 uislands, once in estero bay and had an excellent time both timers; light tackle and fly on the flats and along the mangroves and oyster bars. Say I sent you.
Further south in Chockaloskee I fished with Dave Prickett (941-695-0141) and went 20 miles south of the end of the road, past Chatham River (you *must* read Killing Mr Watson before doing this trip) to a series of Bay's deep at the head of Lostman's River. There I was lucky enough to happen on a square mile or two of bay teeming with rolling 150 pound tarpon. And us with Penn 4300's and 6 and 8 pound test :-).
I cannot recommend highly enough guiding out of eitheer of those areas; the boat ride; birds and scenery is in itself worth the trip regardless of fish.
As for sting rays; booties don't cut it; my wife got a sting ray barb thru the side of a bootie in Islamaroda about 5 years back. Granted she wasn't shuffling as she should have been, but the brab sliced through the neoprene like butter. I think you want a harder and firmer upper than a scuba bootie.
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