A Guide to Sailing in the Florida Keys

For a seamless day sailing the Florida Keys.

What to see and do in the Florida Keys

Heading south from Miami, Key Largo is first in line. This Florida Key hosts America’s first undersea sanctuary – the John Pennekamp Coral Reef State Park. Step off your yacht with snorkels, scuba tanks, or a glass-bottomed kayak. Finding Nemo? He’s right here, along with yellow snappers posing for selfies and lobsters peeking out from coral reefs.

Shhh. The Florida Keys extend just under another 100km (62mi) west from Key West in the form of the Dry Tortugas. This little-known collection of coral islets is protected within a National Park that’s 99% water. The archipelago is linked by an irregular ferry service and hosts a single rustic campsite, making a chartered yacht the ultimate way to arrive. From the deck, spot loggerhead turtles, bottlenose dolphins and magnificent frigatebirds.

Key West’s line of petite marinas is sheltered on the northern side of the island – a stroll away from dozens of oyster shacks and lobster houses. Conch Harbor Marina offers free bikes, document printing and hammocks to sailors who tie-up – plus iced beers, two restaurants and a fishing store. Call ahead or contact them on open VHF Channel 16. Paradise is a tie-up to a mooring buoy off Looe Key – while the island is a National Marine Sanctuary where sea life congregates in droves. Leap over the side to see parrotfish, butterflyfish and jacks. As with all coral reefs, look but don’t touch.

The sustainable larder of the Florida Keys is stocked with stone crabs, mahi-mahi and lionfish – where your menu should include shrimp tacos, Cuban pork and conch fritters. All crowned by a calorific wedge of key lime pie. No establishment on Key West can be considered fancy – Red Shoe Island Bistro simply gathers top drawer ingredients then serves them on the half shell, au beurre, or simply grilled. Harpoon Harry’s is as unabashed as its name – Join salty seadogs for a lobster po’boy or a seafood platter with the works. Pair with Bigger Boat White, a malty pilsner beer brewed in the Waterfront Brewery in Key West.

Sailing a motorized catamaran is a cinch. You can cruise the Florida Keys – with or without a skipper – with horsepower under the bonnet and not a single sail to worry about. Hire a vessel with Dream Yacht Charter, from skippered charters to bareboat fleets, let the captain do the work unless you’re a sailor.

New Market is the marina neighborhood store for pickles and mayonnaise to accompany your lunch on Picnic Island – yes, there’s a clue with that name. The Sunbeam Grocery, a few blocks east of Key West’s marina strip, is bigger and less expensive. Stock up on all-American snacks, international beers and Taittinger Champagne to bring out your inner James Bond.

The Buccaneer Blast kicks off from Key Largo’s Upper Keys Sailing Club each February. The two-day race sees scores of younger sailors compete in Lasters, Optimists and Open Skiffs.

As a yacht charter destination, Florida is fabulous for up to 10 months per year. Easterly winds promise 10-knot breezes through spring and autumn, rising to 15-knots in winter. Best of all, the reefs that surround the “American Caribbean” ward off choppy seas. Sunny? The Florida Keys and Miami Beach are the only places in the continental United States that have never recorded a frost. Winter highs average 25°C (76°F) while sea breezes stop summers from scorching. The only poor period for sailors is between late August and early October when sultry squalls and the occasional hurricane drift in. Sailors are advised to keep a keen eye on tides, too.

Most travelers fly into Miami International airport. The Florida Keys start a one-hour drive south at Key Largo. From here, it’s a sun-drenched 148km (92mi) drive down Highway 1 to Key West. Here, minor airport Key West International welcomes smaller jets from North American cities, including Chicago and New York.

Set sail around the Florida Keys.

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