Stede,
We have our 32' schooner at Fly Creek on the eastern shore of Mobile Bay, across from the Dog River and Mobile.
We've lived here over four years and we enjoy Mobile Bay as a cruising area. Like any area, of course, there are compromises. The bay itself is quite shallow; outside the dredged ship channel, the average
depth in the bay is around 8', and in many areas it's much shallower. Most folks here try to have boats with draft of 5' or less (ours is 2'10" with the
centerboard up) - it opens up more areas of the bay to sail in.
In terms of liveaboards, over on the western shore south of Mobile, there are 2-3
marinas on the Dog River that you'd want to check out. This is probably the closest
live-aboard area to the city of Mobile proper. Here on the eastern shore,
liveaboard opportunities are more limited - there are two
marinas here on Fly Creek, a city marina at Fairhope about a mile south of us, and a pretty nice (and pricey) marina at the Grand
Hotel at Point Clear, another 5 miles or so farther south.
You didn't mention the
LOA of the boats you're considering, but that can limit your marina options a bit. For example, currently at Fly Creek Marina, there are only a couple of open slips that could take anything over about 32' (we're 39' LOA).
In terms of cruising locations, in the upper reaches of the bay there are limited
anchorages at Dog River and Fowl River on the western shore; and really no
anchorages on the eastern shore. It takes 5-6 hours to sail down the bay (winds are predominately out of the southeast); from there you can go east in the
ICW and over to
Pensacola, several nice anchorages and marinas along the way including Ingram Bayou and Pirates Cove; or go west in
Mississippi Sound to the barrier islands, Biloxi and Gulfport, and then on into New Orleans/Lake Pontchartrain, etc.
Coming up from SW
Florida, once you get over onto the
Gulf Coast, you'll have
ICW availability up through Clearwater; then go out into the Gulf up through Anclote Key (Tarpon Springs) and then into the "Lost Coast," from
Hudson up to
Carrabelle. We bought our boat at
Hudson last year and sailed/motored up to Fairhope - if the winds are with you (they weren't with us) you can jump off at Anclote and go direct to either Cedar Key (roughly 20-24 hours) or all the way to Carrabelle/Apalachicola (roughly 24-30 hours). Or you can take the route we did: day
sails up from Hudson to Yankeetown, Suwanne, Steinhatchee and then overnight to Carrabelle/Apalachicola. Unfortunately this involves long, shallow channels at each port, limited anchorages/marinas and not much in the way of towns for reprovisioning. We enjoyed the trip but in the future would hope to do more direct overnight passages to avoid all the shallows.
At Apalachicola you re-enter the ICW and can either follow the ICW all the way up through
Panama City, Destin,
Pensacola and on into Mobile Bay; or jump out at Port St Joe or
Panama City to do day or overnight passages to Pensacola or Mobile Bay. There are a few bridges between Fort Walton Beach and Pensacola that are 50' or less clearance which can impact you depending on your air draft - you might have to go outside no later than Panama City to by-pass them and then go back inside at Pensacola or Mobile Bay.
That's a thumbnail sketch, if you want more specifics either on Mobile Bay sailing or the
passage up from Anclote let me know, I'll dig it out and post it (I've posted it on other sites but I don't think I have here).
Mike Turner
Lazyjack 32 schooner "Mary'Lis"
Mobile Bay, Alabama