The Upper Keys, from Key Largo to Islamorada are home to some tremendous fishing opportunities for the Do It Yourself fisherman. These crystal clear waters hold bonefish, tarpon, permit, snook, redfish and a variety of other gamefish. This area is best fished with a boat but there are some opportunities from shore and better opportunites using a kayak or canoe.
The Keys offer a real variety for the DIY fisherman and your fishing should not be geared toward the typical flats species. There is lots of funn to be had with barracuda, snapper and some of the reef/rock species that are reached from shore. Fishing for bonefish, permit and tarpon on your own in the Keys is tough so be prepared to shake it up and cast for whatever is swimming.
There are several places to access the beaches along the Ocean side including several of the hotels and motels that have ocean front locations. The state and county parks all have access with the oceanside flats at Long Key Beach Park and Harry Harris Park to be some of the best. By renting a kayak you can greatly extend your range and access to beachs to walk and wade.
A great place to go is Pennekamp State Park where you can rent canoes and kayaks. This allows access to the oceanside, Largo Sound where you can find bones, barracuda and snapper. On the bay side of Key Largo are Barnes, Blackwater and Buttonwood Sound which provides wonderful calm conditions for canoes and kayaks and offers some great opportunity for snapper, trout and snook.
One of the ways to access fishing locations is to stay at a hotel or motel that is right on the water and provides access to not only the beach right in front of you but other beaches in the area. I can highly recommend the Pines and Palms Resort in Islamorada as one of those places. It is owned by Jim and Sara Bernardin and Jim is a keen fisherman. If he is there he can help you with where to go and the staff will be happy to set you up with one the guides they work with. At the Pines and Palms they have kayaks for their customers and it is easy to paddly around to a couple of the adjacent bays to walk and wade. Some of the largest bonefish I have ever seen (did not catch) swam right by the dock. You can also fish of their docks for a variety of species as you practice your casting into the wind.
The Upper Keys are easy to get to and provide a nice compromise as a place to visit and enjoy with your family and provide some opportunity to fish. The DIY fishing is not great and access is generally a problem. But if you stay at a beach side location, make sure there are kayaks to rent and you will be okay.
There is a huge (and beautiful) World Wide Sportsman Store (Bass Pro Shops) in Islamorada with lots of local information and maps, it is well worth the visit. Also stop in at Bud and Mary's Marina for the latest information and to hook up with a guide.
Even if you don't catch one yurself go down to ....dock and buy a bucket of fish for a $1 and feed them to the tarpon cruidsing around the dock.