When the weather turns cold and this old boy can't watch his beloved Georgia Dawgs put a whuppin' on their football rivals in the fall, it's time to head south, where the weather suits my clothes. Since the early 1960s, when I first met my college roommate, "south in the winter" has always meant Key West. My roomie was a native Key Wester, called himself a "conch," and probably descended from the first pirates who settled those islands south of Miami.

Before Key West was "discovered" by cruise ships and tourists, it was America — but just barely. The place looked like one of those mythical Caribbean settlements that Jimmy Buffett is trying to sell you — old wood-frame houses on narrow streets with a profusion of tropical flowers and trees that always seem to be blooming. The place was unique, the people were unique, and for a Georgia boy who grew up on boiled vegetables and overcooked meat, the food was to die for — an exotic cuisine somewhere between Cuban and Latin, with strange fruits and gobs of seafood that used liberal amounts of unheard-of spices. I fell in love with the place.

Through college, I spent as much time in Key West as I could. After we both returned from Vietnam, my old roommate and I got there regularly to meet each other's wives and children and watch the place change. By the time my wife, Teresa, and I could afford a sailboat to make the yearly winter trek to Key West, the place was almost unrecognizably honky-tonk from what I'd known in the early years. While the Key West of my memory no longer exists, traces of old Key West can still be found.

Key West By Boat

One thing that hasn't changed is the joy of visiting the Conch Republic by boat. Once Teresa and I retired in 2010 and had more time, we journeyed to Key West aboard Grace, our 35-foot Gemini sailing catamaran. The first few years we joined the trek down the East Coast from our home in Georgia, ahead of the first cold weather. Once in a while we ducked offshore when the weather was favorable. More often, we ground our way down the Intracoastal Waterway, an experience akin to driving through rural Georgia on state roads — a bit novel the first time, drudgery on the way back.

In Florida, south of the Space Coast, one can get to the Keys down the East Coast, but along the way you have to deal with dozens of bridges, heavy boat traffic, and expensive marinas. Or, you can travel west through the Caloosahatchee Waterway and Lake Okeechobee, then head to Key West down the lower west coast of Florida. This route is way more laid back and definitely the path less traveled.

Grace was a shallow-draft cat that would float in a heavy dew, just the boat we needed when we entered the waterway at Stuart and traveled west toward Okeechobee. The only obstacle for our sailboat on that waterway is the Indiantown railroad bridge about 20 miles inland and on the east side of Okeechobee. It looks like something out of an 18th century industrial nightmare — scaly, rusty, and rising from the morning mists like Puff the dragon's evil twin. As it goes up and down, it creaks and groans, and if you're in a sailboat, you hope it goes up to its max height of 57 feet.

When Grace squeaked under, our masthead VHF antenna pinged along the rusty girders overhead, which made me grind my teeth until it was over. From there, the waterway is a leisurely cruise through old Florida, broken by an occasional lock or swing bridge. There's little traffic, the lockmasters and bridgetenders are chatty, and you'll see cattle on the banks. Pull over to the side at night, but beware of the local bloodsuckers that hunt in clouds. Bug spray and screens are as necessary in these parts as plenty of ice-cold drinks.

Then zip through Fort Myers, turn left, and Key West is 150 miles away on a rhumb line due south. But if you go directly there, you'll miss a part of storied old Florida — its southwest coast. Take a couple of extra days to explore Shark River, the numerous keys of the Everglades, and Cape Sable. Same rules apply: This place should be called the Mosquito Coast. I warn you, Pilgrim, when the sun goes down and the wind dies, don't be caught unprepared.

Instead of heading directly to Key West, investigate another road less taken: the sail into Marathon from the north. Then gunkhole down the north side of the keys to Key West where the graceful arches of Henry Flagler's Florida Overseas Railway point the way. Completed in 1905, the railway provided the first means to get to Key West from the mainland. Ferries to Havana and extensive ship traffic to the Panama Canal construction site soon made Key West the most populous city in the state of Florida.

When the Overseas Railway was completed, it was a stupendous feat of engineering. Much of it was built across the shallow water between keys using solid concrete arches that exist to this day. The deeper channels, such as Bahia Honda, were bridged with iron girder structures on concrete piers. The railway was wrecked by the hurricane of 1935 and never rebuilt. Instead, the state built the Overseas Highway over the arches and girder bridges and, until recently, that was the one and only narrow and claustrophobic road to Key West — exciting, to say the least, if you're towing a boat.

If you choose to get to Key West down the east side of the keys, plot a careful course inshore of the Gulf Stream but keep an eye on the depth. Entry into the ship channel from due south can be tricky at night without a chartplotter, or during a heavy weather. And, speaking of wind, understand that Key West is in the open ocean and subject to the same weather one finds at sea. In the winter, that means the periodic cold fronts that sweep through can play havoc in a congested anchorage. In the Keys and Bahamas, the prevailing wind is northeast and blows stink in the winter.

As a cold front approaches from Florida, the wind shifts into the east, then goes south and dies as the front passes over. Visualize a clockwise movement around the compass. When the front has fully passed your local location, the wind will often blow like the hammers of hell from the west until it shifts back to the prevailing northeast. But beware: Sometimes it stalls, sometimes it backs. Be guided by the oldest of the Principles of War: "None of the above is necessarily true." Pay a great deal of attention to the strength and fidelity of your anchoring system.

The Past Is Present

Key West can be a confusing place to navigate, whether you come in by boat, or in a towing vehicle with your boat behind you. Eventually everybody gets to Duval Street, the heart of town. Today this is "tourista central," but when Papa Hemingway was there writing Islands in the Stream, one could look way down Duval Street at noon and see maybe a dozen people, most headed for Sloppy Joe's for that famous lunchtime rum punch eye-opener.

Duval Street was lined with old wood-frame houses way back when, and pretty much now, too. The tropical foliage spilled over the sidewalks and filled the small yards, squawking green parrots filled the trees, and free-range chickens leisurely moved out of your way. The public spaces were filled with exotic flowering trees that seemed to bloom year-round, and the mango and avocado trees provided snacks whenever needed. To this redneck kid from the piney woods of Georgia, it was like stepping into a fantasy.

When Fidel drove his people out of Cuba, many left with nothing and had to fall back on basic skills — such were the cigar makers on Duval Street, who rented the front 6 feet of store fronts and installed small cigar-making operations. You could watch them through the glass as they rolled and packed cigars into hand-made wooden molds. The cigars were premium quality and dirt-cheap.

Another Cuban was Blackie who operated Blackie's Cafe, a gathering place for locals who were up early going to work at the adjacent Navy dry dock, or those who needed a demitasse of heart-stoppingly strong Cuban coffee to cut through the rum they'd been drinking all night. A bowl of smoking-hot, creamy, garlicky black beans from the perpetually cooking pot, along with a couple slices of buttered Cuban bread, was a breakfast that would carry a worker all the way to lunch. Today, as close as you'll get is Buffett's Margaritaville Cafe serving cheeseburgers in paradise, but no Cuban coffee or frijoles negroes.

Sure, there were downers, too. Key West is a desert island essentially without a freshwater supply. The old houses all had cisterns underneath connected to gutters and downspouts just like the rest of the houses in the Caribbean. It rained every day, and water really wasn't a problem ... until the place got discovered. For many years there was a 12-inch water main that traversed the entire length of the Keys from the mainland. The best that one could hope to get from a 12-inch water line that had traveled more than 100 miles was something that looked like a drizzle. It was not intended for bathing but to keep the inhabitants from dying of thirst. Then, in 1967, the new desalinization plant opened, but unfortunately it wasn't much better than the pipe. The best way to get a shower was to stand outside with a bar of soap when it rained. These days the water pressure is better but still a matter of concern during hurricanes.

Mallory Square is the terminus of U.S. Highway 1 (the famed "Mile Marker 0") and Duval Street. Back then, it seemed like all of society's loose nuts and bolts rolled down to Mallory Square and grunged together with their sleeping bags, haversacks, and clapped-out guitars to watch the sunset. For the city fathers, Mallory Square was a stroke of genius to replace the Turtle Kraals that once existed there. That's kraal, as in an Afrikaner livestock pen, except that the pen was a netted enclosure that contained sea turtles. In the old days, folks would pick a turtle to be butchered, then take the meat home to bread and pan-fry it.

Always there was the food — picadillo, paella, ropa vieja, unending seafood, flan, and pie made with real key-lime juice and raw eggs. Key West cuisine is unique because the place is a crossroads between the Caribbean and northern latitudes. The mix of sweet/spicy achieved with native spices such as allspice and ginger, annatto, cilantro, and cumin exploded on the palate of a kid whose mother cooked pork to shoe leather. I couldn't believe what I was tasting! The experience has never left me. Even the silky-smooth dark rum complimented the food, and mojitos made with fresh mint were something that even the poorest folks could enjoy. It was easy to overdo the rum because the stuff went down like ice water, a caution that has also survived in me to the present day.

Pervasive above all in those days was the boating culture. Everyone seemed to have a boat, and most of the people on the island made their living doing something with a boat. The water around Key West was crystal-clear; the reefs teemed with fish, langouste, and stone crab; and the flats all the way out to Dry Tortugas were a playground for a couple of young guys with a boat. Though the water is not quite as clear these days, in other respects the place hasn't changed much. It's still a paradise for anglers, and even though there are many more people, if one looks closely into the corners, you can still see old Key West. The food is still yummy and, if you know where to look, you can still find that wonderful flavor of Cuba.