Which flies should I bring? As far as flies are concerned there are no magic flies so all of the standards the you hear about will work. It just depends on the situation that you are fishing as to what to go to. That being said I recommend a variety of flies (gotchas, charlies, bitters etc) at least with the bones. Around the island I like to go small #6,8and even 10 and I like natural colors tans and olives. I would also mix up the weight, you will encounter deeper water situations up to 5 feet which you could use lead eyes and then the skinny water with turtle grass making no weight and weed guards necessary. The happy medium would be a size 8 with small chain eyes. Everybody has there own favorite and there always different because everybody presents and retrieves a bit different therefore making some flies work for some people and some for others. So mix it up and have fun. I forgot to mention that I like to add rubber legs to some of my bone flies. For Tarpon I like Cockroachs , orange apt tarpon flies and chartreuse or purple toads in sizes no bigger than 2/0. Permit I like merkins and spawning shrimp. Then for snook blue and white decievers and crease flies on top.
Which rods and gear should I bring? An 8wt for bones,9wt for permit, 10-12wt for the tarpon depending on what you are looking for and time of year. If you can only bring one rod I would go with the 9wt for the most versitility. Reels should be of saltwater quality with a smooth drag and plenty of backing. Weight forward floating lines and tapered leaders from 8lbs to 20lbs. Shock tippet for tarpon from 40lbs to 100lbs. You will also want to bring long sleeve shirts, sun screen, bug spray, hat, and good polorized sunglasses.
What is the best time of year to come and fish? Any time is a good time to fish! The large tarpon are the only real seasonal fish which can start as early as May to September. Other than that the real difference is the weather. Windy season is typically November to May but always varies. The Summer June to September can be pretty hot but if you can take the heat and a couple mosquitos the conditions can be great.
How many people can fish in a boat? Two fisherman per boat is the preferred situation. Three is possible if there is an odd man out.