+1 on Florida Bay Outfitters, best kayak shop in south Florida. I don't believe there are any licensed kayakfishing guides unless FB Outfitters has hired one in the last couple of years. Would be skeptical if they recommended one of their eco tour guides for fishing.
I fished Key Largo area a few times from kayak but found other areas within an hours drive in both directions that I came to enjoy much more. Don't get me wrong, Key Largo has some of the most beautiful water, crystal clear, its just that I was mainly looking for bonefish and was new to that type sightfishing at the time. Didn't have much success there and didn't care for the many eco tour paddlers on the water. Florida Bay Outfitters has a heck of a eco tour business there. I kept pushing down the keyes to areas I'd fished and had success catching tarpon and snook with much shorter paddles to productive water and much less kayak paddler traffic. For bonefish, Biscayne Bay in Miami was the my favorite.
The good news, Islamorada is not far down and is the most scenic drive in all the Keys in my opinion. Depending on how accomodating your fishing partners/family are to the idea, I would drive on down and check out Channel 2 bridge (Lower Metacumbe) and Annes Beach. Park (free)in area shown below to fish from fisherman's bridge (it runs parallel to highway bridge and just went through a major upgrade), lots of folks set up tents/lights on it and fish all night. I've caught snapper, snook, tarpon, and monster jacks from the bridge. Very nice folks from all over the world always stopping to watch the fishermen as they made their way to Key West. If you want to fish the area from kayak, you'll turn around and go to Annes Beach...lots of swimmers/waders during summer, shouldn't be that many this time of year or midweek, rarely any kayakers, but best place to launch. Its just a few hundred yards back. Not much area to park in lot. Restrooms, water fountain and boardwalk through the mangroves there. Shallow flats all around, firm sand bottom, best place to swim if you wade out deep enough.
Bridge fishing, sightseeing, and parking at Channel 2 below.
http://goo.gl/maps/S9H4bAnnes Beach parking and launch site below.
http://goo.gl/maps/FFhIxBest chance to hook a snook or tarpon below. If the wind is blowing too hard to kayak, be careful and walk down the rockpile and fish that corner of riprap. Jumbo DOA shrimp in chartruse or glow color, DOA Baitbuster in silver/black back. If current is ripping too strong fish further away from cut so that your bait slows down and has a chance to sink. 15 lb test mainline, 18 to 24 inches of 30 or 40 lb fluro leader with alberto knot to connect. Plenty heavy for fighting fish from kayak on medium heavy bass gear. Not so good if you hook a 60+ lb tarpon from bank or bridge. If you fish from bridge, as heavy as you've got with 60lb leader, ideally at least 200 yards of line capacity. Shimano 4500 baitrunner with 20 lb mono and 7 foot heavy action spinning rod was enough for most anything you'll run into except for big tarpon and grouper.
http://goo.gl/maps/Cqt7PNow if you really want to improve your chances of catching fish without a guide, head to Flamingo. You'll pass right by the road there on the way to Key Largo from Miami or Ft.Lauderdale airports. You can rent canoes or kayaks there, the best snook, tarpon, and redfish sightfishing in all of Florida.
Homestead, Florida the toughest decision I ever had to make, never knew which way I would go unitl the light turned green. Straight ahead to the Keys, left to Biscayne Bay, right to Everglades and Flamingo.
More often than not it was Flamingo.
http://floridakeysmilemarkers.com/
