Skip to main content

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.

Related

05-Sailboats-moored-in-sheltered-waters-off-of-Kärrsön

Charter: Sweden

With 2,000 miles of coastline, 270,000 islands and seemingly countless bays and inlets, Sweden is truly a sailor’s paradise. One of the top sailing destinations here is the archipelago just outside the country’s second largest city Gothenburg (locally known as Göteborg), on the ...read more

fa70b13c-8eec-4c35-b30f-f89e497b469a

Crowdsourcing Age-of-Sail Weather Data

Although big, multi-million-dollar projects like the Large Hadron Collider and the human genome project with their legions of PHD’s tend to grab headlines, there’s still a part of play for the “citizen scientists” of the world. Amateur birders have long contributed to an ...read more

01-LEAD-Ultime-race-Yvan-Zedda,-OC-Sport-Pen-Duick

Ultims to Race Solo Around the World

For years now, maxi-trimarans, both solo-sailed and fully crewed, have been racing the clock on their own around the world in an effort to set ever faster records for the world’s fastest circumnavigation under sail. Back in 2000-01 there was also a no-holds-barred ...read more

P1-01-LEAD-018_CARYNBDAVIS_AMISTAD

Juneteenth on the Water

Discovering Amistad and Mystic Seaport Museum have partnered to organize their third annual Juneteenth festival, featuring concerts, speakers and a reflection on the lasting legacy of racial injustice in America. Declared a National Holiday in 2021, Juneteenth celebrates the end ...read more

Lead-2021-01-17-vue-03-34-av-tb-01

New Multihulls for 2022

Lagoon 51 In keeping with many of the more recently launched models created by French multihull builder Lagoon, the Lagoon 51 is all about comfort, “en plein air,” in particular, as the French might say. Topside, a whopping 80 percent of the boat’s flybridge is given over to ...read more

bermuda

How to Spectate on the Newport Bermuda

The biannual Newport Bermuda Race starts on Friday with the first warning signal at 1 pm. Whether you’re tracking a loved one’s progress or just spectating an event that draws pros and weekend warriors alike, there are plenty of ways to stay up to watch. The starting line will ...read more

03-Hyeres-220429_SOF2022_SAILINGENERGY_1933_3184-copy

US Sailing Strikes Gold in Hyères

After being skunked or nearly skunked at multiple Olympiads, could the US Sailing Team (USST) now under the direction of Olympic veteran Paul Cayard, be finally turning it around? If its performance at the 53rd French Olympic Week regatta in Hyères, France, where the team posted ...read more

P1480042

New York City’s Newest Fleet

120 children enrolled in Brooklyn Boatworks’ STEM and life skills-focused program launched their hand-built optimist prams on June 14 from Pier 2 in Brooklyn Bridge Park. The launch is the culmination of years of student work, with boats in process before the pandemic caused the ...read more