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Tricky Waters: West Side of the Florida Keys

“I always put the fear of God into people that this is the world’s third-largest barrier reef,” says Capt. Joe Dyll of the western Florida Keys, which have long been one of his favorite cruising grounds.

Oh, the places you’ll go!”

When Dr. Seuss wrote these words, he must have had cruisers on his mind. Rare is the cruiser who doesn’t dream of sailing over the horizon, of exploring remote areas. Distance breeds confidence, confidence breeds a taste for adventure, and few vehicles are better equipped to deliver one into the heart of the unknown than a sailboat. 

In the United States and Canada alone, cruisers can find enough challenging cruising grounds to fill a lifetime—places where the scream of an eagle, the spout of an orca or the call of a lonely loon will be the soundtrack to your days afloat. These places aren’t for greenhorns; they beckon to experienced cruisers and demand preparation and judgment. And while they vary greatly in terms of latitude and remoteness, each of these destinations harbors rewards both subtle and extravagant for those bold enough to look for them. 

Read about Pacific Northwest: Vancouver Island

Florida: West Side of the Florida Keys

“I always put the fear of God into people that this is the world’s third-largest barrier reef,” says Capt. Joe Dyll of the western Florida Keys, which have long been one of his favorite cruising grounds. “It starts in Miami and goes all the way down to Key West. I’ve seen everything from small reef fish to 35-foot whale sharks.” 

Dyll adds that draft is often the biggest challenge in this cruising ground, as the western side—known colloquially as “Bay Side”—offers soundings of five feet or less. 

Everglades National Park commands the southwestern tip of mainland Florida. Terra firma here is comprised of mangroves and everglades. Bay Side sailing conditions are characterized by 5 to 15 knot breezes and small seas that usually run a foot or less. According to Paul Keever of Key Largo, Florida, there are islands out in the Everglades that are great destinations, as well as jungle tours that cruisers can make via kayak or—if their draft is shallow enough and their sense of adventure strong enough—sailboat. Because of this, Dyll and Keever both recommend cruising here in a boat with a lifting keel or centerboard, or aboard a multihull. 

As for provisioning and cruising amenities, large grocery stores abound, 3G-cell coverage is ubiquitous (so you can get weather forecasts and communications on your smartphone), fuel and water are easily acquired and, as Dyll jokes, “showers are 50 cents, and it usually costs two dollars to watch.” There are also plenty of boatyards for repairs and Sea Tow is locally active. 

According to Keever, the most commonly sustained cruising wounds from going aground on the Bay Side are broken rudders and busted props. Keever reports that the charts are accurate, but he’s also quick to advise that there’s no substitute for local knowledge, especially when negotiating an unknown, coral head-studded harbor entrance.

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