As Claude said, this is a long haul for one day trip, but doable. Much more enjoyable if you do it in two days. Several good anchorages along the way though. Once out of the lake you can anchor just west on the Hwy.90 bridge, on your port side, across from Ft. Pike. Also when you come out of the Rigolets, you can snug up behind Rabbit Island, although this time of year it may be somewhat buggy. From there on to Gulfport, you can pretty well sail and enjoy. And be careful of shallow water in the places Chuck mentioned. If you go through Pass Marianne, stay in the channel. Some real shallow water on both sides. If you go around the south side of Cat Island, be careful. I have not done that way recently, but since Katrina, the charts are not too good. Other than these two places, there is plenty of water all the way. Have a nice sail.