A Guide to Sailing in the Florida Keys

Known for coral islands and sandy picnics, the Florida Keys are an incredible sailing destination
Known for coral islands and sandy picnics, the Florida Keys are an incredible sailing destination | © Stephen Saks Photography / Alamy Stock Photo
Tristan Rutherford

There are over 880 reasons why the Florida Keys are the best yacht charter destination in America. This endless chain of coral islands wiggles from Miami to Key West in a sandy necklace licked by the sun. Only 30 of the islands are populated – mainly by lucky park rangers and oyster shack shuckers. Anchor off the hundreds of other Florida Keys for dolphin spotting, mangrove kayaking, desert island picnics and whirlpool-warm seas. Access? Solely by sea.

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.

Pack a telescope and a stargazing app to spot Jupiter, Venus and Mars. Less than 100,000 people live in the Florida Keys, who are blessed with cloudless nights and unpolluted skies. The sandy beaches of Big Pine Key are the only place in the United States where astronomers can see the Southern Cross constellation. Park yourself under a palm tree and look to the heavens.

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.

A banded butterflyfish swims through the ring of a Spanish galleon anchor encrusted with corals and sponges in the Florida Keys

Best mooring locations in the Florida Keys

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.

Sailboats docked at the Conch Harbor Marina in Key West in the Florida Keys

Where to eat and drink in the Florida Keys

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.

Harpoon Harry’s Restaurant and Bar in the Florida Keys

Best charter options in the Florida Keys

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.

An elevated view of sailing ships in the Florida Keys

Where to get groceries in the Florida Keys

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.

Key annual sailing events in the Florida Keys

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.

Climate and weather in the Florida Keys

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.

Sailing boats sit on South Beach in the Florida Keys

How to get to the Florida Keys

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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