Aaron Maynard owns an electric-­bike shop in Myrtle Beach, South Carolina, where a customer came in one day seeking a folding bike. 

“I asked him specifically why he wanted a folding bike because we sell many models,” Maynard says. “He said that he and his wife were going to sell their house and their belongings, and move onto a sailboat for a few years. After he left, I looked up ‘45-foot sailboat’ online. What I saw totally enthralled me. I began researching boats nonstop. I ordered a catalog from The Moorings and read it from cover to cover. In the back of the catalog, there was information about learning to sail.”

The next day, Maynard called Offshore Sailing School and signed up himself and his wife, Michele, for a certification class. They had never set foot on a sailboat when they attended the Offshore Sailing School at the South Seas Island Resort on Captiva Island, Florida, in 2018, joining the increasingly large ranks of people who are taking certification courses either to learn the basics or to gain advanced skills.

And make no mistake: It’s far from just newbies like the Maynards signing up for classes these days. For boat ­owners, some insurance companies require sailing certifications, and some charter companies have tightened up certification ­requirements for bareboat sailing as well. 

John Gaston was an experienced sailor and boat owner who had completed basic and intermediate cruising certification courses in Canada. He was looking for advanced cruising certification when he came across Barefoot Offshore Sailing School in St. Vincent and the Grenadines. He knew the school’s instructor, Rob McLean, who was associated with the courses in Ontario. Gaston signed up and completed his Sail Canada Advanced and Offshore courses in the southern Caribbean.

“I find that taking sailing courses provides excellent training to prepare for situations and response options,” he says. “I would rather learn from other people’s training and experience because you don’t know what you don’t know. A sailing course tends to be a safe and controlled environment.”

Taking the classes helped the Maynards and Gaston live their sailing dreams. The Maynards went on to complete multiple certifications, purchased a yacht and placed it in a BVI charter fleet, and have chartered 14 times over the years. They also bought a boat that they keep closer to home. Gaston recently completed an offshore sail-training trans-Atlantic crossing. 

Class Is In

No matter what sailing interests students have these days, there are classes available to help them achieve their goals. The American Sailing Association has certified close to 600,000 sailors at more than 400 sailing schools around the globe. 

Jonathan Payne, executive director of ASA, says that he sees two common paths in ASA sailing education. “One, someone takes in interest in local sailing courses. They make a long-term commitment to learn at a sailing school near where they live and attend weekend classes,” Payne says. This typically takes six weeks.

The second path, he says, is a ­weeklong destination school. “This is a full-­immersion, intensive course where students do a fair amount of study before arriving,” he says. “Once they are there, they are in class and running maneuvers sunup to sundown. The skill-building happens on the water.”

Of the two paths, the sailor who studies locally over a longer period might build a broader base of knowledge, while the other might be looking for a deep dive into the aspects of chartering. “A student in a course stretched out over six weeks might learn more about sail trim and sail theory, whereas someone on board a boat 24 hours a day might learn more about seamanship, bilges, and troubleshooting the engine,” he says. “There are certain things that happen on the water when you’re living on a boat. You have the opportunity to learn ­problem-solving in the moment.”

For the ASA local courses, Basic Keelboat Sailing (ASA 101) teaches skills inside a marina. Basic Coastal Cruising (ASA 103) takes the student outside the marina, and up and down the coast. Bareboat Cruising (ASA 104) is required to charter a boat.

“You can learn to sail in Colorado on your weekends, or sign up for a charter yacht in Greece,” Payne says. “There are a lot of options.”

US Sailing, the governing body for the sport of sailing in the United States, offers similar building-block tracks: Basic Keelboat, Basic Cruising and Bareboat Cruising.

Doris and Steve Colgate, founders of US Sailing-certified Offshore Sailing School, come from a racing background and have more than 160,000 graduates in over 60 years of teaching. Offshore offers one-week training courses in Florida and the British Virgin Islands, where students earn certifications for boats up to 50 feet. 

Students attend for a variety of reasons, according to Beth Oliver, vice president and director of sales and marketing. Some are new to sailing. Others are veteran sailors who want to experience the BVI. “These are people who either want to charter on their own, or who are considering purchasing a yacht and living aboard,” Oliver says. “They’re adventure-seekers with an active lifestyle, and want to share this enthusiasm with like-minded people. Many of our students are highly educated professionals, so continual learning is important to them. They like to share their skills with family and friends. Many want to pass on the sailing lifestyle to their children and grandchildren as a sort of legacy.”

 For those who want to charter, Offshore offers a combination course: Fast Track to Cruising. “We like to say that we can take you from your couch to the captain’s chair in one week,” Oliver says. Textbooks are sent in advance, and students arrive at class prepared to learn.

Offshore is the official sailing school of The Moorings, one of the world’s largest charter companies. The Moorings offers Offshore Sailing School courses in the BVI and Royal Yachting Association courses in the Mediterranean, according to Amanda Kurland, charter sales representative for The Moorings and Sunsail. These sister companies offer several levels of courses in multiple places. Sunsail has destination sailing schools in the United Kingdom, Croatia, Greece, Australia and Grenada.

Some people do the training because they want to purchase their own boat when they retire, Kurland says. Others are jumping from lake sailing to ocean ­sailing. Still others have the goal to ­charter a bareboat.

Blue Water Sailing School, an ­ASA-certified school in Fort Lauderdale, Florida, offers destination sail ­training charters closer to home. These are seven-day liveaboard courses where the vessels anchor out at night. Classes are available in Florida, Rhode Island, the Virgin Islands and the Bahamas. 

Blue Water owner David Pyle says that he also finds two basic groups of people looking for sail training: those who want to go cruising on their own boat someday and those who want to charter. “We try to get students to a point where they’re comfortable, confident and safe on a boat,” Pyle says. “It’s kind of like getting a pilot’s license to fly a small plane. You can get the training and certification, but of course you want to be safe and competent before you fly a plane on your own.”

Pyle says that approximately 15 to 20 percent of basic-level students return later for advanced courses. “We get a lot of people who have this goal to purchase their own boat,” he says. “They want to see if this is for them. I was just talking to a couple from Nebraska. They’ve never sailed, and they’re interested in finding out if this is for them. This is not uncommon.”

Pyle and Oliver agree that the most challenging aspect for students is often the amount of material they need to learn. Most students are also fairly anxious when it comes to docking. “Students who have been away from testing for a while might get nervous about the written-test ­component, but our instructors determine each student’s learning levels and preferences, and work with them individually, quizzing everyone each day on topics, so most are very comfortable by the time they take the written tests,” Oliver says.

There’s a lot of repetition and refreshing as the course goes along. Some students fear that they lack the physical strength for sailing work, but the sailboats have equipment such as winches to assist the student with maneuvers. Other students have a general fear of the water and ­seasickness, but most of that can be overcome with time on the boat.

Pyle says that it’s not uncommon to work with sailors who have had smaller boats, such as a 25-foot boat on a lake, but now want to go coastal sailing on a 40-foot monohull or offshore sailing on a 50-foot catamaran.

West Coast Multihulls in San Diego runs a sailing school with training on multihulls. Students who complete AS 101, 103 and 104 can take ASA 114: Cruising Catamaran Certification. It’s a five-day liveaboard class offered around Catalina Island and in the Sea of Cortez.

“We are catamaran experts with the largest sailing catamaran fleet on the West Coast,” says Guinevere King, general manager at West Coast Multihulls. “People come to our school to learn how to sail catamarans and experience the liveaboard cruising lifestyle in Southern California and in the Sea of Cortez.”

Most students want to get ASA 114 certifications while building their sailing resumes so that they can bareboat charter. “We also have a large percentage of our students who are looking to buy a catamaran and cruise the world with family and friends.”

 West Coast Multihulls also offers ASA 105 and 106 advanced courses for experienced sailors. The company recently added ASA 107 and 108, which cover celestial navigation and passagemaking.

“Our instructors share their knowledge and expertise with their students in a supportive environment,” Kurland says. “Our students gain confidence and invaluable real-world experience on board, which you can’t replicate by watching a YouTube video.” 

Barefoot Offshore Sailing School ­instructor McClean says that because there are so many levels and types of courses available, he doesn’t see a typical student but rather a thread that links them all. It’s people who want to sail, who want to live on a boat and learn for a week, who want to go offshore.

“Fifteen percent of our students are new to sailing,” he says. “Forty to 50 percent have already taken an initial course and are there to advance their skills.” The school welcomes all levels, he says, “but we do encourage people to take that first level at home. Someone can get far more out of their investment if they can learn the basics of tacking and jibing before coming to the Grenadines. It’s an ideal location for learning. You’re exposed to 8- to 15-knot winds, waves offshore off the islands, and a guaranteed variety of good winds.”

McClean says that the most important skill, in any context, is ensuring the safety of the crew and skipper. Other tough skills for students include navigating in ­unfamiliar waters, understanding weather, and anchoring at night. “Probably the most challenging [skill] we teach is crew-overboard drills,” he says, adding that students practice in multiple circumstances at multiple times. “If you’re not confident on all points of sail and you can’t manage a beam reach, then you need training and practice.”

After the introductory and ­intermediate courses, some students apply for advanced courses, including sailing at night. Some want to learn offshore sailing on a trans-Atlantic course. “We have a discussion with them to verify that this a good match for them,” McClean says. “The last thing they want is to wake up and find that this is the last place they want to be.” 

Award-winning journalist Theresa Nicholson is CW’s senior editor.

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Forget the hurricanes: It’s business as usual at Blue Water Sailing School, which reopens December 2, 2017, in St. Thomas, in the United States Virgin Islands. Most of its fleet was not in the Virgin Islands and sustained no fall storm damage.

The school’s base, at American Yacht Harbor in the village of Red Hook, St. Thomas, offers courses through the American Sailing Association curriculum. Among them are Course A+ Cat: Bareboat Catamaran Skipper, a one-week liveaboard cruising course, and Course A: Bareboat Monohull Skipper, starting mid-January 2018.

For more details contact Blue Water Sailing School (www.bwss.com).

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Offshore Sailing School has announced two women-only sailing weeks next April and May to take women from novice or little sailing experience to competent sailors capable of handling large cruising boats up to 54’. Taught by expert U.S. Sailing-certified instructors, the women-only program mirrors the school’s popular Fast Track to Cruising® course – an eight day program that results in gaining three levels of US Sailing certification. Taught by US Sailing-certified women instructors at the bareboat cruising level, these special weeks are “designed to fulfill the three C’s of sailing,” says Offshore Sailing’s President and CEO, Doris Colgate. “Those three C’s are Confidence – in yourself, the boat and those with whom you sail; Comfort – with all the factors that go into feeling at home when you sail; and Control – of your sailing destiny, where you go, how you go and when you go.” But Colgate says there is a fourth C that has to be achieved before all the others kick in, “and that is Competence – which is the focus of all that we do at Offshore Sailing School.”

Colgate should know. She started sailing at age 27 when she took a Learn to Sail course at Offshore Sailing School, and then fell in love with (and married) the school’s owner, Steve Colgate, “and the school,” she says. She has been advocating for women to learn how to successfully and competently handle sailboats of all sizes ever since. In 1990 she founded the National Women’s Sailing Association, and two years later the not-for-profit Women’s Sailing Foundation. “I want women to be able to see the world under sail with the self-assurance that comes with knowing how to sail well,” says Colgate.

Available at the school’s locations on Captiva Island, Florida, and Scrub Island in the British Virgin Islands, the Fast Track Women’s Weeks start with two days learning basic to intermediate sailing skills on a Colgate 26, and then six days aboard learning skills to handle 43’ to 54’ cruising monohulls or 39’ to 48’ cruising catamarans, all while making new friends and memories in a comfortable environment.

The special women-only Fast Track to Cruising programs are April 29-May 6 at South Seas Island Resort on Captiva Island, Florida, and May 19-27, 2017 in the British Virgin Islands, at Scrub Island Resort, Spa & Marina. Cruising boats available in Florida are two Jeanneau 439s and a Leopard 48 catamaran. In the British Virgin Islands, women will sail on a Moorings 3900 catamaran and Moorings 54.5 monohull. No more than four women students and a woman instructor will be on each boat.

Arrival is Friday before the course begins Saturday, and ends the following Saturday. Course packages range from $3,995 to $6,500 depending on the size of the cruising boat, and whether participants are signing up for a private or shared room ashore and private or shared cabin aboard. Packages include full week course tuition, professional instructions, three nights’ resort accommodations ashore with room tax and daily resort fee, shared or private cabin aboard the cruising boat for five or six nights depending on location, welcome party first night, dinner ashore the night before the cruising course starts, all meals and snacks aboard the cruising boat plus two dinners ashore during the cruising course, graduation celebration, special women’s week logo shirt and hat, Doris Colgate’s book Sailing – A Woman’s Guide and three US Sailing textbooks (for each level of the course), three US Sailing certifications culminating in Bareboat Cruising Certification, diploma and logbook, and one year complimentary Cruising World magazine subscription. All participants also enjoy automatic first-year membership in US Sailing, and in the Offshore Cruising Club for world-wide flotilla sailing vacations led by Offshore, discounted membership in BoatUS, and first-time discounted charter benefits from The Moorings.

Offshore Sailing School was founded in 1964 by Olympian, America’s Cup Sailor and National Sailing Hall of Fame Inductee, Steve Colgate. The school provides a full range of sailing instruction with US Sailing certification – from beginning sailing to advanced cruising and racing – at seven locations in Florida, the British Virgin Islands, New York and New Jersey. In addition, the Company conducts team building programs for corporations and groups, and leadership training for universities, including Emory’s Goizuetta Advanced Leadership Academy. More than 140,000 adults and their families have graduated from Offshore Sailing School programs over the past 52 years. For more information and hi-res images, contact Beth Oliver, Director of Sales and Marketing – Boliver@OffshoreSailing.com or call 239-985-7516. Visit OffshoreSailing.com for more details

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It felt like finals week in college all over again. While I sat desperately trying to study, nearby I could hear the parties thrown by those whose responsibilities were behind them. Only this time, the revelers were the patrons of William Thornton, better known as Willy T’s, the pirate ship turned dive bar in the back corner of the Bight at Norman Island, in the British Virgins, and my study materials were the textbooks provided by the Colgate Offshore Sailing School in my Fast Track to Cruising course.

Perched in the ­cockpit of our Beneteau 50.5, I tried to ignore the thumping of bad ’90s rap. The whirr of a blender from our galley drowned out the music for a passing moment, and seconds later, through the companionway came my instructor, Brian, who handed me a perfectly blended piña colada. Maybe this wasn’t quite like college after all.

The Fast Track to Cruising program is one of a handful offered by Colgate Offshore Sailing School in an effort to educate and vet future charter customers. Its partnership with The Moorings gives graduates a sort of passport to Moorings charter fleets around the globe, save for a few locations that require further testing or certification.

The program I signed on with involves two days of learn-to-sail instruction followed by four days of bareboat chartering classes. Those who already know how to sail can test out of the first portion or, like I did, jump into a Colgate 26 for a two-day instructional refresher.

My family chartered a handful of times when I was growing up. Back then, though, my dad, an experienced sailor, would show up at a charter facility and answer a few questions, and then they’d hand over the keys to a 50-something-foot cruiser without any additional checks or balances, waving us off. While undoubtedly many miss the simpler days of bareboat chartering, I for one am thankful that I followed a full curriculum and have total confidence in my ability to skipper a sailboat for a week. Plus, hands-on learning in the Caribbean never hurts.

During our week of fun in the sun, we went over everything from man-overboard drills to docking under power, points of sail to heaving to. With three written and three sailing tests conducted over the course of the week, our curriculum was just serious enough for us to be learning, but just relaxed enough to let us still have fun.

Our cast of characters seemed comical at first, but the spaciousness of the Beneteau 50.5 kept us all friendly throughout the week. There was me, the 25-year-old editor on a mission; our instructor, Brian, who has been a part of the Colgate School for years and is currently on a two-year stint in the BVI (not too shabby); a couple from Colorado hoping to soon retire and live aboard; and a man from Brooklyn with dreams of chartering with his wife and two daughters.

While the course is certainly structured to accelerate those with little to no sailing experience from novice to confident charter captain, it’s equally beneficial for those looking to reinforce their skills before embarking on a solo command. “The important part of the first couple of days on the C26 is to learn basic sailing skills, or brush up on what you already know,” says Kevin Wensley, Offshore Sailing School’s director of operations. “We cover how to steer by the telltales, how to maneuver, and how to handle MOB situations. It’s easier to learn on a small boat because it’s so responsive. You get immediate feedback to any adjustments you make.”

After those first two days, students switch over to a Beneteau 50.5 charter boat, a cushy 50-foot monohull with five cabins and, yes, air conditioning. “The performance is great,” says Wensley. “Fifty feet is as big as an average-size family is going to want to take out, so we want to give people experience aboard.”

“The Moorings is very standardized across the fleet,” adds Ian Pederson, marketing manager for The Moorings, which is under the TUI Marine umbrella. “You can charter the same model boat that you learned on anywhere in the world that The Moorings has a base.”

Well, almost anywhere. A student who completes his or her certification in the BVI can then charter any monohull, up to 50 feet long, at bases in countries that don’t require additional paperwork. The International Proficiency Certificate can be obtained through a simple application process with no additional testing, and several charter companies offer courses that can help you meet other certification requirements for primarily Mediterranean chartering.

Though we didn’t make it out of sight of Tortola at my Fast Track to Cruising course, it’s easy to fantasize about all the places your certification could take you. Christine Cooper and Bruce Putzman, two of my classmates, plan to retire soon and buy a boat to sail around the world and live aboard. In the meantime, they plan to charter. “The goal is for us to learn how to sail together the best we can,” Cooper told me one night while we were moored off Jost Van Dyke. “There are so many amazing places in the world that we’ll get to see once we’re both competent sailors.”

Over the course of our week together, Christine and Bruce; our other classmate, Steve; and I certainly became competent. We practiced docking drills on Scrub Island, picked up a “man-overboard” buoy in the calm waters off Virgin Gorda’s Baths, and even snapped a halyard, learning firsthand how valuable The Moorings’ support team is; at Scrub Island, the Moorings staff arrived with a replacement boat, and within hours we were underway again with fully functional rigging and without any headache from repairs.

While the course is rigorous, there’s still time for plenty of fun and enjoying the beauty of bareboat sailing. We snorkeled into caves, fed 6-foot tarpon from the docks at Scrub Island, and played dozens of raucous games of Yahtzee late into the night.

Though our end goals were unique, my classmates and I arrived back at The Moorings’ base six days later fully confident in our abilities to charter independently — an assurance immediately put to the test as we left instructor Brian behind in Tortola for our final night of sailing. After a relatively uneventful evening (except for the four attempts it took us to grab our mooring), the next morning we returned to the base a final time no worse for wear and having survived our first night of true bareboat chartering.

For me, completing the course didn’t just mean I would have the opportunity to enjoy charter vacations with my fiancé and future family, just as I did with my family in the past; it was also a validation of the valuable sailing lessons my own dad had taught me on those long, lazy trips around the islands when my brother and I were kids. I look forward to the day when I can invite my parents on a charter, take the helm, and hand my dad his own piña colada.

Lisa Gabrielson is the associate editor of CW’s sister publication, Sailing World.

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