I live in Fort Walton Beach and sail the Choctawhatchee bay often. If you are going to be here for a few days, I would recommend bringing the Mac. Every weekend, the big crowds are at Crab Island (just north of the destin bridge), Norriega Point and Destin Harbor. Personally, I avoid those places. Spectre Island, marker 50 just south of Hurlburt Field, is a nice place where you can overnight camp/anchor. There are numerous places where you can launch, depending on where you will be located. If you have the mast up, you won't be able to go to the mouth of many of the bayous--Rocky Bayou, Cinco Bayou, etc because of the low bridge clearances. But, there are plenty of nice anchorages without going into them. I like the cove in Nelson Point for overnight anchoring or up into Boggy Bayou. A good sail might be up into Boggy Bayou to get dinner at Dockside and then anchor up there for the night or close to the bridge in Valparaiso--just a little south. If you want to be adventurous, you can go out the Destin Pass and sail the gulf, but that pass gets pretty rough if the tide is running against you and the winds are strong. You can stay overnight at the FWB landing for free, just have to let the city know. If you give me specifics of what you are looking for, I can try to help out. I think you'll really like it down here, but be warned it is really hot and humid in the summer and we typically get isolated T-storms everyday at 4PM. Oh, the local yacht clubs race every wednesday night around 5:30 from Fort Walton Beach and Bluewater Bay...a good time to go out for an afternoon sail and watch.
-david