From someone who has fished every square inch of Florida since I first moved here in 1982, I will recommend Everglades City/Chokoloskee/10k Islands. Flamingo is good too, but you will have much faster access to both types of fishing (Back country & flats) out of 10k. You design the trip to be as “Text book” or “Adventurous” as you want it to be. Adventurous meaning………….there are very few expeditions that compare to heading south through the 10k and/or the wilderness waterway, camping on small sand/shell barrier islands or on designated chickees, fishing along the way and taking in all of what “Old Florida” has to offer……..eventually making it down to Flamingo and heading back north. I’ve done this trip many times by boat, and hands down (IMO) the overall experience is simply awesome. You will be one on one with nature, the diversity and the excellent fishing of the everglades. I would not do this solo on a kayak your first time around. From a text book standpoint, you will have endless miles of daily backcountry and fishing from a yak. “Follow the tide out and follow it back in”. Bugs are not too bad this time of the year………..but bring plenty of hard core bug repellent just in case.