More info needed
GuyHSome things will depend on what you would like to do,and some on your boat. You can stay inside completely as far as Pensacola from Ponchatrain. After Pensacola, you will have make offshore runs if your mast if over 50'. You can make day sails to Destin, Panama City etc. You can do Pt.St.Joe to Appalachicola inside. After that you have to go outside to at least the Clearwater area. This is a 24 hour run, or a tad more depending on boat speed and weather. From there south you can stay inside most of the way down to the Keys. If you want to make a straight shot it is approx. 4 days from the Pascagula entrance to the south end of Sanibel island, Fr. Meyers area. If you decide for the offshore route, be sure to check the weather forecast carefully, and also the gulf loop currents. Depending on the currents you may want to stay closer to shore, or maybe pick up a boost at some point. I am familiar with the area as far south as Ft.Meyers, Sannibel area. Some very good sailing down there, but if you stay inside you will be pretty dependent on the engine most of the time. Offshore is some pretty fantastic sailing. Get a good cruising guide, and have fun. Some really nice anchorages along the way. If you have any more specific questions drop me a line.