We have been here all of our lives, and live in Slidell, LA. We have sailed from here to Destin so many times. From what we read, the Gulf Coast is much more lay back and cruiser friendly than South FL., where we have never cruised. In fact we now are very apprehensive about even bothering with south FL because of the Florida water cops (except for The Keys, where we would probably use a mooring ball). Just don't want to be bothered when anchored. Not so bad in the panhandle. We have been stopped once while at anchor
in Big Lagoon, near Pensacola, by FWC. Fairly friendly and not requesting boarding, just checked papers. AL. WC are similar. They seem to have anchoring time limits but we have never been approached. They seem to be mostly focused on power boaters with DUI issues and speed.
Mobile Bay has several facilities which are LAB friendly. We have stayed at Turner Marine, on Dog River, for several months. The MS. coast also has a few but some are not LA friendly. Pass Christian Manicipal Harbor no longer allows LA. There are now new marinas in Gulfport, Long Beach, Biloxi, Ocean Springs, and back into Bay St. Louis, and Waveland on Bayou Caddy, but I am not sure of restrictions. Too many casinos around for my taste as it is always very busy and noisy.
There are quite a few marinas on Lake Pontchartrain which allow LA and a few which do not. Many of those are located a decent distance from the Lake up various bayous or rivers and are quite safe from most weather problems.
Once you leave Lake Pontchartrain, where there are a few good anchorages, and head east, good protected anchorages are hard to come by until you enter the ICW on the eastern shore of the Mobile Bay. After entering there you come to the very best anchorages on the GC., Roberts Bayou (PIRATES COVE), INGRAM BAYOU, BIG LAGOON. A friend rode
out "IVAN" in '04, in Roberts Bayou. These are as good as it gets IMHO and are all good for anything less than a hurricane.
If you head west out of Pontchartrain and enter Lake Maurapas there are numerous bayous and rivers, which are considered, by locals, to be totally hurricane proof. Most are also very still and quiet for total peace. You must have a 50' stick, or less, to transit the area between the lakes. Have never been, on our boat, as we are too tall. There are also marinas up most of these waterways.
The offshore Gulf Islands are quite exposed, especially with winds from the North, with a fetch of 8 to 10 miles from the mainland. The water around all of them is very shallow and shoals rapidly. As long as the wind is blowing S, SE, SW you are good to go. That said, we have visited each of them, every year since 1973 and have had few problems, other than an occasional bumping . The bottom is usually good, hard, deep sand, good holding, but nasty, sticky, anchor
hugging, mud is very common in most places.