The Tradition and Passion of Sailing the Emerald Coast

Reading the Wind

Sailors read the wind on the water as you might read a great novel. Wind lines are new chapters that guide and propel them toward grand destinations, and approaching squalls are plot twists that must be surmounted to further their character arcs. Home to some of the most stunning cruising grounds on the entire Gulf Coast, Florida’s Panhandle has provided sailors with a long and continuing history that stretches back to the early 19th century as boats under sail were transitioning from one of utility and transportation to one of sport and recreation.

Troy Gilbert

Whether you are a cruiser or a racer, distance regattas on the Gulf Coast are a true adventure and a beautiful and unforgettable life experience. They also offer up the opportunity to earn those stories that are best told at your favorite beachside watering hole.

With few bluewater regattas remaining on the Gulf Coast, the annual Gulfport to Pensacola Race held in June has become one of those graduation regattas for young or up-and-coming sailors looking to build an offshore résumé and perhaps a crew slot for the Mexico Race and beyond. For cruisers, it can be a weekend-long excursion that ends with sailors enjoying the hospitality of the Pensacola Yacht Club and its legendary bushwacker cocktail.


The biennial Regata al Sol — or as it’s more commonly referred, the Mexico Race — is run by both the Pensacola and Southern yacht clubs and will next be held in May 2016. Sailing from Pensacola Bay to the rustic 6-mile-long island of Isla Mujeres just off the shores of Cancun, this 555-nautical-mile race is a true bluewater regatta and a unique experience. Racing and cruising classes sail for five days across the electric blue waters of the Gulf of Mexico, and then crews and “racer chasers” effectively take over the island with four days of events and legendary parties.

Professional solo sailor Ryan Finn earned some of his chops sailing on the waters off the Panhandle and, at 37, has spent a few years racing in the European circuits.

“Pensacola is a natural destination and host for these distance regattas with its easy access to the Gulf of Mexico and hospitality,” Finn said. “Whether finishing the race from Gulfport or disembarking for the island shores of Mexico, the Panhandle has a unique connection for all the sailors from the Gulf Coast.”



Onboard, these amateur and expert crews revel in the hours spent under sail and on the water. As the sun sets and meals are rustled from the galley below, stories and laughter are shared while the spray coming off the bow becomes saltier and the lights from the cities and towns vanish as they sail south from the Gulf Islands. These men and women are sharing an adventure, a sport that is more akin to wilderness expeditions. It creates enduring bonds and experiences, and the legacy gets passed down from generation to generation.

Ask any collegiate sailor under scholarship who aspires for the Olympics and he or she will tell you about skills acquired sailing small 8-foot Optimist dinghies at yacht clubs throughout the country. In fact, talk to most sailors and they’ll not hesitate to describe how they learned self-reliance out on the waters under the guidance of junior sailing programs. The Panhandle is home to several excellent accredited junior sailing programs, including Fort Walton Beach and St. Andrews Bay yacht clubs, but the program at Pensacola Yacht Club, helmed by Olympic windsurfer Bert Rice Jr., is one of the better ones in the region.

“Our programs are all about developing a love in these kids for being around the water,” Rice said. As the sailing director, Rice handles a fleet of 10 Optimists and a number of other classes of dinghies for junior sailors. “They all have to pass a swimming test. They need to already have a little bit of fish in them, and then we expose them to different boats to discover what they enjoy. Over time, we are able to see which ones enjoy racing, and we groom them and train them up for our racing program.”

Whether you are a sail or power boater, these programs start a lifetime love for the water for kids by simply instilling the sense of adventure, self-reliance and the freedom found in boating — and yacht clubs are a great avenue to do just that. Most clubs run two- to four-week-long summer camps and teach sailing instruction, seamanship, boating safety and navigation before sending the kids, many as young as 6 years old, out on protected and supervised waters in the Optimist dinghies that are used by junior programs throughout the world. As the kids learn and become more skilled in sailing the dinghy, they eventually graduate to sailing Opti regattas against other clubs and then can graduate to even larger junior regattas held throughout the United States and possibly even world championship events.

Ashley Sukalski, 32, has long been active in sailing at the Fort Walton Yacht Club and along the entire Gulf Coast through the formal inter-club association known as the Gulf Yachting Association.

“The GYA is very active in racing, which is great for anyone from kids to adults, but the Florida Council of Yacht Clubs all throughout Florida is ideal for older people who tend to be more into cruising,” Sukalski said. “They both have their benefits. I’m an active racer and enjoy the camaraderie.”

Surprising is the groundbreaking leadership role of women in the sport over the years. In a time well before women had the right to vote in this country, all-female-crewed boats were openly competing against men — and not without some disconcertion from a segment of their old-school male counterparts. There are several documented examples of all-female crews and regattas on the Gulf Coast dating back to 1904, and today female skippers, crew and regattas are common.

While regattas are the most publicized events and are certainly daunting for individuals with little to no sailing experience, racing constitutes a scant 15 percent of the on-the-water activities. Cruising sailors, whether affiliated with a club or not, make up the vast majority of the sailing population. On weekends, it’s easy to spot groups of eight to 10 cruising sailboats gathering together and sailing out to the barrier islands or to destination marinas such as Lulu’s Homeport or the Wharf at Orange Beach.

It is a liberating escape for families to set out on relaxed sails for the barrier islands and anchor in those quiet lee shores. Turning off the PlayStations, the iPads and grilling the day’s catch off the stern of a sailboat over cocktails as the kids learn to crab or simply run their feet through the sand — such experiences last a lifetime.

With the Gulf Islands and their legacy of pirates and Civil War-era forts within easy reach for day sailors, it’s hard not to get wrapped up in the romanticism of sailing. The ideal method to get acquainted with the lifestyle is to finally accept that invitation out on a friend of a friend’s boat, or walk the piers during the fun weekly “beer can” races at your local club and introduce yourself to skippers who may be looking for dedicated crew willing to learn. In addition to junior sailing camps, there are multiple courses available for adults, women only and even singles along the coast.


Aspects of this world may appear daunting to the uninitiated; however, with most seasoned sailors decked out in flip-flops, it should not be surprising that they are readily accepting and willing to teach people who feel the call of the water. There are families beginning their legacies on the water every day and learning what it means to have that sail full in the breeze and those island shores within their grasp.

Sailing Race Roster

The northern Gulf Coast is home to some of the oldest regattas in North America, including some that have continuously been raced since 1850. Geographically, the Florida Panhandle has always been heavily involved with their counterparts in Louisiana, Alabama and Mississippi, especially with offshore or bluewater distance regattas.

While the field of these great offshore events has narrowed on the Gulf Coast over the decades, it is notable that two of the largest and most prestigious that remain are directly linked to Florida’s Emerald Coast. Always a draw for sailors, especially the large and active racing scene in New Orleans with deep ties to the beaches of the Panhandle, it is a common sight to see 50 to 60 boats rafted up at the yacht club piers and hailing from Mobile, Biloxi, Gulfport and New Orleans.

Navy Cup Regatta — Buoy Racing: Navy Yacht Club, June 13–14

Gulfport to Pensacola Race —100 nautical miles: Southern, Gulfport and Pensacola yacht clubs, June 27–28

Big Mouth Regatta — Buoy Racing: Pensacola Beach Yacht Club, Aug. 22

WFORC — Buoy Racing: Pensacola Yacht Club, Oct. 16–18

Regata al Sol —555 nautical miles: Southern, Isla Mujeres and Pensacola yacht clubs, May 7–12, 2016

Categories: On the Water