Sailing the Florida Keys

  • Photo of Sailing the Florida Keys
  • Photo of Sailing the Florida Keys
  • Photo of Sailing the Florida Keys
  • Photo of Sailing the Florida Keys
  • Photo of Sailing the Florida Keys
  • Photo of Sailing the Florida Keys
  • Photo of Sailing the Florida Keys
  • Photo of Sailing the Florida Keys
Photo of Sailing the Florida Keys
Photo by flickr user eutrophication&hypoxia

Between Florida and Cuba is the gentle arced chain of 1700 islands of the Florida Keys, a place that's not quite America, but not quite the Caribbean, but with many of the best bits of both. There are a few really good reasons these islands make a perfect sailing destination:

1. There's no language barrier.

2. The weather is tropical.

3. The islands are the exposed parts of a coral reef, which means they're close together, covered in white sand and lush vegetation, and underneath them there's brilliant diving and snorkelling. The island's also have their own endemic species of plants and animals.

Sailing the Florida KeysThe arc of islands runs for 106 miles with the Atlantic Ocean on one side and the Gulf of Mexico on the other, and as well as world class sailing diving, snorkelling and Key Lime pie, the Florida Keys are also known for their fishing grounds. Key Largo is the the first island off Florida's mainland and Key West is the farthest away, about 100 miles to the south, and between them the other thousand or so are dotted, some small and uninhabited, perfect for secluded moorings, and some busy hubs, known for knowing how to have a sunny, laid back good time.

There are a vast number of potential sailing trips in the Florida Keys. There are organised trips lasting anywhere between one day and one month, and if you want to plan it yourself there are many charter companies to choose from, offering everything from your basic boat to a luxury cruiser complete with a jacuzzi and all the trimmings.

The four basic options if you want to organise it yourself are:

Chartered Sailing: book your boat with a captain/ and or crew depending on your craft's size.

Sailing Training: if you want to learn to sail you choose a boat that's relatively easy to handle and comes with a captain who will train you into crew.

Bareboat Charters: if you're already a sailor you can lease your boat without a captain or a crew.

All Inclusive Charters: these ships come complete with captain, crew and cook, so you can just relax and enjoy the view.

Beyond that there's hundreds of potential routes to choose from. Here are just two examples, both lasting a week and beginning in Miami.

Miami to Key West

Underwater visit to the 'Christ of the Deep'Most charter companies get people settled onto their boats from about 10am. With the rest of the first day sail to the Biscayne Bay National Park then stay overnight at Pumpkin Key. If you're interested in diving them on the second day chart your course to the Carysfort Reef and Key Largo Dry Rocks the visit the statue of Christ of the Deep. Find a spot in one of Key Largo's marinas for the night. Key Largo is one of the largest ports in the region and the best place to pick up unusual supplies. One of the main industries is fishing, which also equates to excellent seafood restaurants. It’s also in a good position between the Everglades National Park and the Dry Tortugas National Park, where you can hope to see both turtles and dolphins. There's a group that have been known to swim alongside boats, escorting them between Garden Key and Loggerhead Key.

Dry Tortugas National ParkIf you're seeing the sights you might want to stay another day here, if not weigh anchor and head for Windley Key which has some of the nicest beaches in the Keys.

On the forth day sail on to Duck Key and on the fifth to Boot Key which has more excellent snorkelling opportunities. Close by is Looe Key, another excellent Key for snorkellers. The final leg of your journey is between Newfound Harbour Key where you spend your sixth night and Key West, which you should aim to reach in time to the Sunset Celebration held every evening in Mallory Square before heading out to Sloppy Joe's on Duval Street. Joe was a friend of Hemingway, one of Key West's best known locals. Most charter companies will let you drop your boat off there and you can hire a car to get back to Miami on the Overseas Highway.

Miami round trip

This second option follows the first up until Duck Key on the fifth day. From there you have to start turning back towards Tavernier Key via Lower Matecumbe Key, which is near a sunken Spanish galleon if you're interested in wreck diving. On the sixth day plot your course for Caesar's Creek Channel and find a protected spot there for the night, then on the seventh day head back to Miami Beach via Elliott Key and Dinner Key.

It takes about three days sailing to get from Miami to the Upper Keys and then in season another week to sail all the way through to the Bahamas, which is tempting once you’re settled into the lifestyle and the sun and sea. From Miami it’s Elliot KeyPumpkin KeyKey LargoIslamoranda.

The tropical weather means you can sail here all year round, but the best time of year for sailing the Florida Keys is March though May and the last two weeks of November and the first two of December. The hurricane months, when you also have to contend with humidity and mosquitoes, are June through to November, with a peak in July, August September, and October.

Expect your sailing views while amongst the keys to be wide and flat. Most of the islands are flat and the ocean is pretty flat on top of the reefs. You can also expect wealthy people in big yachts and speed boats cutting up the water. And sun, expect lots of sun and a really laid back atmosphere all round.

Comments by other travellers

We launched in Stuart, then anchored in Peck's Lake, then spent a few nights at the anchorage in the north end of Lake Worth and a few nights at Old Port Cove Marina, then a night in a slip at the Palm Beach Yacht Centre (since it was stormy), then a night at Lighthouse Point Marina at the Hillsboro Inlet, then cruised to Bahia Mar in Fort Lauderdale where we spent a couple of days in a resort like atmosphere, then anchored for a week in Sunset Lake in Miami, then a few days Dinner Key Mooring Field in Coconut Grove, then a few days anchored in No Name Harbor in Key Biscayne, then a night at a slip at Elliott Key, then one night anchored out at Steamboat Creek, then a night anchored out at Tarpon Basin, then several days slipped at Plantation Yacht Centre, then a night anchored out at Fiesta Key, then we ended our journey at Marathon, where we stayed two weeks at City Marina. I blogged the whole trip. It was amazing.

1 Reply

Thanks for that - I'll get my map out...

There is no doubt that the Florida Keys are one of the greatest places to sail in North America. We trailered our 26-foot sailboat down this winter, and starting from Stuart, cruised to Marathon, the sailor's mecca, via the Intracoastal Waterway. It was one of the best trips ever. I have hundreds of gorgeous photos of the journey. Two months of aquamarine waters, glorious sunsets and friendly laid back people!

1 Reply

Sounds amazing - what was your itinerary?

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