We sail a 22' Starwind 223 in 10-12 day trips at choice sailing destinations like the Long Island Sound, the Outer Banks, the Chesapeake Bay, etc. First of all I would advise you to trailer the boat to the Keys. It would take you close to 2 weeks just to get there and back. If you just want to experience the sail from Gulfport to the Keys then at the very least position the trailer down there so that you can bring the boat back and do not have to do the same trip twice. We have two coolers that conveniently fit under the companionway step. One is for food and the other one for drinks. The less you open them the longer the ice will last. You do not have to stock a lot as there will be opportunities to re-stock along the way. We will stock food for about two days and by then we are ready to re-stock ice and fuel. We carry two gallons of drinking water for cooking and other necessities. We also fill a sun-shower which we carry on deck attached to the mast. Bathe with a bucket of salt water and then rinse with the sun-shower. Joy is the best detergent that works in salt water to do dishes. take 13 gallon garbage bags that you can tie around the stanchions until you reach a dumpster facility. Also take cloth pins so that you can dry bathing suits and towels. We try not to cook aboard but merely reheat. Prior to departure we will prepare some food and freeze it so that it will last longer in the coolers. Our 2 stroke Nissan 9.8HP burns 1 gallon an hour and we have a 3.5 gallon tank feeding the engine and also carry two 5 gallon jerry cans tied to the stanchions. Take a small battery charger with an extension cord and a 30A adapter to recharge your batteries along the way. We usually plan for every third night to hit a Marina to take a hot shower, recharge batteries and re-stock supplies. Speaking of Marinas take a Florida West Coast cruising guide that includes the Keys with you. It will help you to plan your stops. Marine charts are essential, a compass, a handheld GPS and a handheld VHF radio will complete your navigation package. Keep an eye on the weather and stay relatively close to shore this would mean rounding up Florida Bay. Getting into and navigating the Intracoastal anywhere from Ana Maria to Naples is an option in foul weather, make sure you know the possible entry points and keep in mind always your distance to any of them. We have done this in the past and it is always an option to arrange to leave the boat at a marina and catch a ride back home to continue the trip at a latter date. Someone said cruising is about doing maintenance to your boat in distant places so take a small but well assorted tool box and some spares. My last advise is to budget some money for entertainment and sightseeing during stops. I have known some people that sailed to a destination and never got off the boat . For that they could have anchored close to home and would have had a similar view of the shore.