Miami and the Florida Keys by Superyacht

There are few departures in yachting as theatrical as leaving Miami. You slip out through Government Cut with the towers of Brickell hardening in the morning haze astern, the beach running away to port, and within an hour the mainland has thinned to a green line and the water has turned the particular pale green of shallow ground. Ahead lies a chain of islands that curves south and west for something like a hundred and twenty miles, ending in a town that has always been more Caribbean than American. The Florida Keys are the only tropical cruising ground in the continental United States, and they sit close enough to the Bahamas to feel like the start of something larger. A week here is not a passage-making week. It is a slow, warm, shallow-water drift down a reef line, and it suits a superyacht better than most people expect.

Miami: The Departure City

Miami earns its days before you ever untie. The city's waterfront is best read from the water, and the run through Biscayne Bay past Fisher Island, Star Island and the Venetian Islands is the cleanest way to understand how the place is arranged — a city of causeways and private islands where the front door of a great many houses faces the bay rather than the street. Ashore, the Art Deco district along Ocean Drive holds its pastel geometry against the beach, and Vizcaya, the villa James Deering built on the bay in the 1910s, still presents its stone barge to the water exactly as it was designed to be approached: by boat.

Timing is worth a thought. Each February the city fills for the boat show, and Miami becomes the centre of the yachting world for a week — wonderful if that is what you came for, and worth avoiding if it is not. Either way, Miami is a serious provisioning and crew-change port, which is why so many Keys charters begin and end here rather than in Key West.

Biscayne Bay and Stiltsville

South of the Rickenbacker Causeway the bay empties out and Biscayne National Park begins — a national park that is almost entirely water, protecting the bay, the mangrove shoreline and the northern end of the reef. On the flats near the Key Biscayne channels stand the last of the Stiltsville houses, a scatter of timber cabins raised on pilings out in open water, survivors of a much larger community that hurricanes reduced over the decades. They are strange and wonderful to pass at slow speed, and they mark the moment the cruise properly begins.

From here the geography dictates everything. The Keys have two sides: Florida Bay to the north-west, which is beautiful and almost uniformly too shallow for a yacht of any size, and the Atlantic side, where Hawk Channel runs inside the reef from Key Biscayne all the way to Key West. Hawk Channel is the road. It carries the depth a larger yacht needs, it is sheltered from the ocean swell by the reef itself, and it puts the day's diving a mile or two off the beam. Your captain will spend the week on it.

The Upper Keys: Key Largo and Islamorada

Key Largo is where the reef announces itself. Offshore lies John Pennekamp Coral Reef State Park, established in the 1960s as the first undersea park in the United States and now bordered by the wider Florida Keys National Marine Sanctuary, which protects the only living coral barrier reef in the continental United States. Molasses Reef is the best known of the dive sites here, and in the shallows nearby stands Christ of the Abyss, a bronze figure set on the seabed with its arms raised, visible from the surface on a calm day and a genuinely moving thing to swim down to.

The sanctuary shapes how the week is run, and for the better. Anchoring on coral is prohibited, and free mooring buoys are laid on the reefs so that visiting boats can tie up without touching the bottom. A professional crew will have the tender on a buoy and the guests in the water within minutes of stopping, and nothing gets dragged across four thousand years of coral in the process.

Islamorada, a little further down, has built its name on fishing and has never really needed another one. The flats behind the islands hold bonefish, permit and tarpon, stalked in inches of water from a skiff; a few miles the other way, the Gulf Stream runs close enough offshore to put sailfish and mahi within a morning's reach. Alligator Reef, marked by its skeletal iron lighthouse, is the snorkelling stop most crews choose here. It makes a good day: skiff at dawn, reef after lunch, and the yacht never moving more than a few miles.

The Middle Keys and the Lower Keys

The middle of the chain belongs to Marathon and the Seven Mile Bridge, the long low span that carries the Overseas Highway across the widest gap in the islands. Alongside it stand the remains of Henry Flagler's Overseas Railroad, an extraordinary piece of early twentieth-century engineering that ran trains to Key West until a hurricane took it out in the 1930s; the old bridge sits derelict and photogenic beside the new one. Just west, Bahia Honda has the best beach in the Keys by common consent — an honest arc of sand facing open water, unusual in a chain where most shorelines are mangrove or rock.

Past the bridge the islands grow quieter. Big Pine Key is the home of the Key deer, a miniature subspecies found nowhere else and protected by a national wildlife refuge that covers much of the island; they are small enough to be startling the first time one steps out of the pines. Offshore, Looe Key is the reef the lower Keys are known for, a spur-and-groove formation inside the sanctuary that on a still morning is as good as snorkelling gets in North America.

Key West

Key West is the point of the whole thing. It sits ninety miles from Cuba and considerably further than that from the rest of Florida in temperament — a town of tin roofs, shuttered conch houses, roosters in the street and an unembarrassed appetite for its own mythology. Hemingway's house on Whitehead Street is still there, still full of the descendants of his cats; Fort Zachary Taylor guards the southwest corner with the best swimming beach in town below its walls; and every evening the crowd gathers at Mallory Square to watch the sun go down over the Gulf, which is either the most charming ritual in Florida or the most commercial, depending on your mood.

A word on logistics, because this is the one place in the Keys where they bite. Deep-water dockage in Key West is in real demand and the largest yachts often cannot be accommodated alongside, so many lie at anchor off the island's northwest side and run guests in by tender. It works perfectly well, and it is worth knowing in advance rather than on the day — this is a stop your broker and captain should be squaring away weeks out.

Dry Tortugas: Seventy Miles Further

For those with the time, the Keys have one more thing to offer, and it is the best of them. Roughly seventy miles west of Key West, out where the charts empty, lies Dry Tortugas National Park — a handful of low sand islands, superb water, and on Garden Key an enormous unfinished nineteenth-century brick fort, Fort Jefferson, sitting improbably in the middle of the ocean with a moat around it. The snorkelling along the moat wall is excellent, the seabird colonies on the neighbouring key are nationally important, and because almost everyone else arrives by ferry or seaplane and leaves the same day, a yacht that stays the night has the anchorage largely to itself. It is an overnight run each way and it wants settled weather, which is precisely why so few charters do it and why the ones that do never stop talking about it.

When to Go

The Keys season runs through the northern winter, roughly December into April, when the humidity drops, the north-east trades settle in and the water clears. Christmas, New Year and the weeks either side of the February boat show are the busiest, and command premium rates accordingly. Late spring is the quiet reward — warm water, long light and far fewer boats — while the summer months are hot, still and prone to afternoon thunderstorms, and the Atlantic hurricane season runs from June to November, which is why most yachts are elsewhere by then.

That elsewhere is often north. The same fleet that works the Keys and the Bahamas in winter runs up the coast for the American summer, and a charterer can follow the same rhythm: a February week on the reef, a July week among the mansions and islands described in our guide to Newport and New England. One coastline, two entirely different holidays.

The Keys reward a yacht that is planned around them — the right draft for Hawk Channel, a tender programme built for reef days, and a captain who knows the water well enough to pick the right mooring at Looe Key on a busy Saturday. Explore the charter fleet and speak to the Ahoy Club team, who will match a yacht to your dates and handle the detail from the Miami berth to the anchorage off Fort Jefferson.