Outside Doris and Steve Colgate’s bedroom window, overlooking the Caloosahatchee River, clouds take and release sunlight like stained glass. Dragonflies zip in and out, coursing across a widening channel. Their translucent wings disappear into a translucent sky.
The couple is absorbed in the reopening of the Fort Myers Beach location of their US Sailing-certified Offshore Sailing School. The beach site and their 36-year-old Fort Myers office were lost to Hurricane Ian, along with five boats and so many paper memories. Their scrapbooks, filled with newspaper clippings marking races won and medals earned, and relics commemorating business and wedding anniversaries—all of it was left in tatters.
There were photographs of the boats Steve and Doris helmed from one edge of the earth to the other, including the 81-foot racing yacht he steered in stretches of seven hours; hours that felt like minutes. There were portraits of Doris in her florid red sail jacket and Steve peering over a map filled with islands looped like constellations.
Vintage 1973 photo courtesy Offshore Sailing School
Doris buried the books in baking soda, hoping to salvage, well, anything. But the scrapbooks were a loss. “We’re survivors. We always have been,” she says. “When you know how to navigate through the challenges at sea, the challenges that occur in life become inconsequential.” Their commitment to each other and their work continues to carry the couple as they move through their 80s and consider handing the reins to trusted staff.
Doris and Steve met in 1968 when Doris, a sailing novice, took a job at Yachting Magazine in New York. Her coworkers recommended she take a course at Steve’s Offshore Sailing School. Doris recalls the first time they met—the bathing suit she wore, the floral cover-up. “I walked down to the docks to find him. He was working on the boats out there, and the minute I saw him, I fell in love,” she says, her voice lilting. The scrapbooks may be gone—their loss is immeasurable—but the memories remain.
While Offshore Sailing School has locations in St. Petersburg, Key West and the British Virgin Islands, the Colgates call Fort Myers home. They have cultivated strong relationships with local resorts, like ’Tween Waters Island Resort & Spa, where they run their Captiva Island school, and Pink Shell Beach Resort & Marina, where their Fort Myers Beach site recently reopened.
Offshore students navigate between Pine Island Sound and the Gulf of Mexico, both ideal for sailors with enough wind to keep boats from running aground. A few decades ago, sailboats were a rarity on our Gulf shores. Now, they can be seen as easily from land as from water. Sailcloths dot the azure waves beneath the Sanibel Causeway, like puffs of cotton, carried to and fro, waving at the cars above.
Steve discovered his passion for sailing while out on the water with his family as a 9-year-old boy on Long Island Sound. He was tasked with bailing water out of the sailboat—a chore he happily took on. “I feel whole out on the water,” he says. A part of the notable Colgate family (his ancestor, industrialist William Colgate, founded what would become the multinational personal care products company Colgate-Palmolive), Steve was a member of the 1968 Olympic sailing team, wrote textbooks on the sport and became a fixture on the racing circuit. Doris echoed Steve’s passion, then matched it, becoming a champion of women’s sailing. “[It’s a] mutual admiration society,” Steve says. “I can never believe how much Doris is capable of on the water, and off it.”
In the early years, when Steve competed along, Doris ran the company. Long-distance races, from Massachusetts to Spain, proved difficult, as the two went weeks without contact. “No one had cell phones, and the boats kept a code of silence, so their competition couldn’t track them,” Doris says.
Back home, the couple spent their days in close quarters, aboard a sailboat or in their 300-square-foot apartment, with only a folding table and roll-out couch. The distance when they were apart was immense, but Doris was lifted by thoughts of Steve skirting the Spanish islands and pushing the boat through wayward winds on the open water.
On the boat together, Steve likes to steer while Doris scans the water for navigation marks, each empowered and working in partnership with the ocean. Through sailing, the couple has been able to crisscross the globe, going ashore in tiny villages and hamlets from Greece to Tonga in the South Pacific. They’ve immersed themselves in local foodways in Norway and Sardinia, where they’ve spent days meandering earthen streets awash in saffron. Plenty of times, they’ve dined on fish gathered in baskets straight from the sea and mangoes plucked from low-hanging branches on an island.
The couple imparts the gift of exploration to the hundreds of sailors they’ve trained. “‘I can’t believe I did this’ is the reaction we hear most,” Doris says. In the school’s most popular course, the eight-day Fast Track to Cruising, students find their sea legs on a 26-foot training boat before taking the helm of a mid-size cruiser. Newbies are astonished each time the wind picks up their sails, their boats reliant on nothing but air and water.
The Colgates no longer sail as much as they used to but remain committed to their students and the community they’ve cultivated. Both of them were inducted into the National Sailing Hall of Fame (Steve in 2015 and Doris in 2022), and Doris is on the board of directors for Florida Repertory Theatre.
Photo By Brian Tietz
Photo By Brian Tietz
The future of sailing in Southwest Florida and beyond concerns Steve, especially as powerboats turn electric and silent, rivaling one of the sport’s main draws: the noiseless glide. Still, Steve says, no machine-powered vessel can match the challenge and adventure you experience when it’s just you and the elements. On a sailboat, you’re feet from the water, with nothing to deaden the sounds of the lapping waves, the wind’s whisper in the sail. “Once a person has experienced sailing, they are converts,” he says.
As the sun sets over the Caloosahatchee, the Colgates watch the sailboats glide across the water, their silhouettes etched against a fiery sky. When the couple thinks of the future, they’re confident Offshore will endure and continue to grow as it has since 1964, blossoming from a one-branch, two-boat passion project to a celebrated institution, unrivaled in the industry.
Photo By Brian Tietz
With time, the school will chart its own course, propelled by the constant winds of change, and a new generation of sailors will take the helm. But the Colgates’ spirit will remain, woven into the billowed sails flashing against the coral sky, a testament to the enduring power of their love and the sport that brought them together.