Pensacola - where thousands live like millions wish they could.
http://www.visitpensacola.com/
We have none of the traffic, congestion, or expense of central or south Florida. The cost of living here is about as low as you're going to find anywhere on the coast. We have a large protected bay to sail in, and numerous bayous and lagoons as well as the Intracoastal Waterway to explore and gunkhole. We have something like 30 or 40 miles of National Seashore, where the barrier islands have no development and you can anchor in a protected cove in the sound and dink ashore to explore miles of sugar white beach. Our marina is right next to Sherman Field, which is home to the Navy's Blue Angels, so we have free airshows twice a week as they practice. We're small enough to still feel like a town and not a city, but big enough to have pretty much anything you'd want. Our new waterfront baseball stadium opens next month, home of the Blue Wahoos, a AA farm team for the Cincinatti Reds. If you need a bigger city, we're 45 minutes from Mobile, AL, 2 1/2 hours to New Orleans, and 5 hours to Atlanta. We personally sail from early March until late November or early December, and then do maintenance and upkeep in Jan and Feb. We just hauled and did our bottom between Christmas and New Year, and were back in the slip the first week of January.
The downsides are that we do have an actual winter, with temperatures sometimes hitting the '20s and even the upper teens (but not usually for very long). Waterfront property is very expensive, but if you don't mind living ten or fifteen minutes from the water, you'll find great deals. Like all of coastal Florida, home owners insurance for anything near the coast is crazy expensive, and possibly even unobtainable, throwing you into the state's high risk pool. Marina fees are pretty pricey, running on average $10 to $14 a foot per month. If you're retired military, you can get a great slip at the Navy base like ours for $7.25 a month including utilities, and it even comes with 24 hour armed security (hey, it's a military base!). We do use a diver to keep our bottom clean. We paint with a hard modified epoxy, and then pay $75 a month for a monthly cleaning. You could certainly do it yourself if you dive. But we only have to do our bottom about once every three years, so it all evens out more or less. Although there's abundant deep water, with the bay averaging 25 to 30 feet, it does get a little thin around the edges. But we have soft sandy bottoms around here, so we've never touched bottom where we couldn't just back ourselves off, and have never damaged anything.
It's a very popular area for retirees and snow birds. You should check us out.