There are basically 2 channels " if you wanna stay in the ICW " that run to gulfport.
Being a tugboat rather than sail boat, ive made that passage too many times to count.
The one member here that i know can help from experience is nice-n-easy. He lives off the lake and sailed many miles eastwardly. THe south Marriane channel is well marked as well as grand isle channel. When you come out of the ICW into lakebougne just follow the channel to grassy island, turn NE toward st joe light and grand isle channel.
That is what we call the south channel. To the north is an old channel that runs up toward gulfport. keep grassy island off your stern and there are only 2 " two " green day boards about 3 miles apart. that lead you to the north channel. If you want shoot me an e-mail with contct info and we can discuss it in detail.
Hey, Chris..That is agood run.. you'll have to leave very early in the morning to make that in one day.. Once you get out of the Rigolets, the sailing is fine. The "spoil areas" shown on the chart are deep enough for you to cross so you can sail as the wind carries you and ya don't have to stay in the channel EXCEPT .. when you get closer to Gulfport and have to get through Merrill Coquille and Pass Marianne.. You have to be in the channel to get through there.. very shallow water and pretty far out .. Have a good trip.. Here is a web site that you can use to look at the area where you are heading.. http://marine.geogarage.com/routes
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.