EVER WONDER HOW YOU JOIN THE RANKS OF THOSE WHO CAN WALK INTO A MARINA AND RENT A QUARTER-MILLION-DOLLAR YACHT? YOU NEED TO GRADUATE FROM AN OFFSHORE SAILING SCHOOL, AS FORMER LANDLUBBER ROGER TOLL DID.
It is blowing 20 knots out of the east. We’re beating hard on a northeasterly tack toward our anchorage for the night, and our 44-foot sloop is on her ear, heeling so far her rail is buried in the water. photos by chris rogers
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lace crochet cover-up by milly; sunglasses by oakley
learning curves
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learning curves
sailing school
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e’re overpowered,” I shout to my three companions. “We have to reef the mainsail.” Like an experienced crew, my wife, Kathryn, jumps to the mast to switch the furling winch, Erica eases the outhaul and Taylor opens the line clutches on the inhaul and pulls the mainsail in a little. In less than a minute, the boat is sailing more upright, weather helm has eased and our speed is nearing 6 knots from 41/2, the most we’ve gotten out of her since leaving the marina several hours earlier. It has been a perfect afternoon of sailing, but already the sun hangs low on the horizon. After a long day on the water, we look forward to reaching a safe harbor, anchoring the boat, diving into the warm bay, then opening a bottle of wine and toasting our success. After all, we have something to celebrate. A week earlier, we were newcomers to serious sailing, and now we are captains of our own yacht.
River, one on Long Island Sound, one on the Chesapeake Bay, one in the British Virgin Islands and one in Abaco, Bahamas. “How’s the trim of your jib, Roger?” asked instructor Kevin Wensley, standing near the stern of a Colgate 26. I’d not noticed “Capt.” Erica’s slight change in direction, and the foresail was now sheeted in too tight. Kevin, who oversees the school’s Captiva-based branch at the South Seas Island Resort, taught with a deft touch of native British wit, a lot of positive reinforcement and in-depth knowledge from 15 years of racing.
We arrived on Captiva—an island just off the coast of Fort Myers, Florida—with the same sort of apprehension a child might feel about his first day at school. Four of us—two couples who had never met each other— headed to our first session of Offshore Sailing School’s Fast Track to Cruising, a nine-day course that would carry us from the basics of sailing right up to all the knowledge we’d need to charter a “bareboat,” the term for a liveaboard sailing-cruiser that you drive yourself, like a rental car. Understandably, chartering companies like to see credentials and a sailing résumé before handing over the keys to a quarter-million-dollar yacht. So, short of already being an experienced sailor, the only way to get qualified is to take a course from a respected school. We had selected Offshore Sailing School, which has 10 locations—four in Florida, two on the Hudson
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It was Kevin who guided the four of us (Kathryn and I, along with Taylor and Erica Ruggles, a couple from Washington, D.C.) through a daily regimen of classroom learning, followed by two three-hour sessions of practical training. Once we’d completed the course and passed our exams, we’d be American
polo by milly
When four people go in on it, leasing a bareboat can be less expensive than a resort, and it’s a lot more mobile.
Sailing Association certified in Basic Keelboat (101)—the first stage of a multitiered certification program. Typically, we took turns steering, tacking, jibing, heaving to, setting the spinnaker, practicing man-overboard drills, tying knots, learning the lingo, and studying nautical rules and regulations. Offshore Sailing School’s founder, Steve Colgate, knew that sailing would be his life as soon as he crewed on a transatlantic race at age 19. After graduation from Yale and a stint in the Air Force, he founded the school in New York City in 1964. His wife, Doris, now president and CEO, worked with him on finances and marketing while he amassed a résumé that includes two America’s Cup races, 19 Newport, Rhode Island– to-Bermuda races, eight transatlantic races and the Olympic Games. Frustrated with the sailboats they were using for teaching, Steve also—with help from naval architect Jim Taylor—designed his own boat, the Colgate 26, which the school uses for all its basic and high-performance teaching. “Steve believes in challenging students to get them out of their comfort zones,” Kevin told me. “Even if you’re an accomplished sailor, there are things we teach that you won’t know.” I understood what he meant: That morning, while we were tacking furiously into a strong headwind through a channel about a boat-length wide, he taught us how to sail backward, or “stern first.” On our way back into the marina, with a strong wind blowing, he had us drop our sails just in time to slide up to the dock. New skills
came at breakneck speed, and each time one of us took the tiller, Kevin would up the ante, adding yet another complex variation. On the third day, we scored high marks on our Basic Sailing test, an 80-question multiple-choice exam provided by U.S. Sailing, the sport’s governing organization. As a graduation gift, Kevin handed over the Colgate 26, which we sailed out to the Gulf of Mexico by ourselves, each taking turns leading our mates through our favorite maneuvers and drills. The next morning, we boarded the school’s 44-foot Hunter, our home for the remaining five nights of school and the last two stages of the syllabus, Basic Cruising and Bareboat Cruising. With its roomy salon and three cabins, it seemed like a mansion after our opencockpit racer, but our now practiced eyes saw that the Hunter, with its simplified systems and self-furling jib and mainsail, would be easier to sail than the sportier Colgate. Cruising is to performance sailing what an RV trip is to a Formula One race. It’s about touring in transparent waters, relaxing in the lee of a tropical isle and sitting on deck in a beautiful bay. When four people go in on it, leasing a bareboat can be less expensive than a resort, and it’s a lot more mobile. And chartering companies suggest routes to suit one’s level, complete with suggested anchorages, idyllic picnic beaches, and useful information on currents, tides and hazards. “Living on board this boat while learning the basics of
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learning curves sailing school
Dare to Go Bare(boating)
About 3,000 students a year attend Offshore Sailing School’s various courses, from beginner to advanced navigation and racing, at 10 locations between New York and the Caribbean (State University of New York Maritime College, Fort Schuyler, New York; Chelsea Piers, New York; Liberty Landing Marina, Jersey City, New Jersey; The Inn at Perry Cabin, St. Michaels Maryland; South Seas Island Resort, Captiva Island, Florida; Pink Shell Beach Resort & Spa, Fort Myers Beach, Florida; Mansion House B&B, St. Petersburg, Florida; Hawk’s Cay Resort, Duck Key, Florida; The Moorings, Road Town, Tortola, British Virgin Islands; and The Moorings, Marsh Harbour, Abacos, Bahamas). Fast Track to Cruising offers instruction in the first three levels of certification necessary for chartering a bareboat. Info: 800-221-4326, 239-454-1700 or www.offshore-sailing.com.—R.T.
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Cruising is to performance sailing what an RV trip is to a Formula One race.
bilge. Before getting under way each morning, Andy taught a session on the diesel engine, for instance, or on anchoring and docking, the water system, pumps and plumbing, or the basics of navigation. On Andy’s last evening on board, we anchored off Useppa Island, its mangroves dotted with white herons like decorations on a Christmas tree. The sun dropped low on the horizon, igniting distant clouds in fiery hues of peach, orange and canary yellow. It felt timeless, healthy, unstressed, and we talked like old friends. Kathryn cooked rosemary-garlic potatoes, Erica made a salad, Taylor put a grouper on the barbecue and I opened another bottle of wine. Around us, neighboring boats turned on anchor lights at the tops of their masts, which appeared like bright stars in the gloaming. The next day, we took our last two exams, passed again with high scores and dropped Andy off at the South Seas Island Resort marina. For the next 24 hours, the Hunter 44 was ours. We pointed our bow back to Pelican Bay in a wind that whipped up whitecaps, taking turns as skipper of a quarter-million-dollar yacht. After a four-hour sail, we cautiously motored into our anchorage with the depth gauge indicating a mere half-foot clearance below our keel. We touched a sandbar, but Taylor quickly threw the engine into reverse and we pulled away. The breeze off the sea was strong despite our protected harbor as we set the anchor and let out 100 feet of rope. During dinner, the wind died, then shifted 180 degrees as the land cooled, picking up again until it neared 20 knots. The boat swung with it, and we scurried back on deck, nervous that we might collide with neighboring boats that also lay at anchor. During the night, we took turns coming up top to reassure ourselves that the anchor was holding. Just before dawn, I awoke, made a pot of coffee, then watched the narrow band of red in the east lengthen into day. Kathryn soon joined me on deck. “You know, maybe we should chuck it all, buy a boat and try sailing the Caribbean for a couple of years,” I suggested, under the influence of the morning. “Why not?” she answered, her eyes shining as bright as the rising sun. When Sky Contributing Editor Roger Toll isn’t enjoying the mountains of Utah, he is often found sailing on Caribbean seas, and with his new expertise, now more than ever.
polo and shorts by lija; opposite page: silk cover-up by tory burch
cruising is a true-to-life experience,” said Andy Cross, our new instructor, who learned to sail as a child on Lake Michigan. “It combines a cruising vacation with a lot of learning.” And with knowledge fresh from our Basic Sailing course, we had more time to just cruise. Life on the Hunter was relaxed, with each of us taking turns steering at the helm while others trimmed the sails, practiced knots or studied for the next two exams. The boat cruised along between 3 and 5 knots depending on the wind, which was brisk the first day as we sailed north in the Gulf of Mexico toward our anchorage in Pelican Bay, near Cabbage Key. Taylor and Erica shared duties, taking turns at the helm, manning the sails, and while two cleaned up below deck and latched things down for sailing, two others washed down the decks and checked the motor oil, generator, water tanks and
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