I knew how to sail, but I was never properly taught how to return a boat to its mooring. So I was like an airplane pilot who knows how to fly but can’t quite figure out how to land.

Tired of playing bumper cars with other boats in the marina, I decided to take another sailing course. And like thousands of other people, I wanted to do it in Florida or the Caribbean. After all, if you’re going to be out on the water, it might as well be beautiful and swimmable water, right? And it helps to have reliable winds.

Would it matter which of the many sailing schools I chose? You bet, because every school is unique. Some emphasize day-sailing, some stress racing, others teach skills required for bareboating (sailing a sleep-aboard boat), and some offer a combination of the above.

But even when competing schools’ courses seem similar, they may not be. First of all, different schools teach you on different vessels. Second, they employ course outlines and certification standards mandated by different agencies, primarily the American Sailing Association, U.S. Sailing, and the Royal Yachting Association.

So deciding where to learn or improve your sailing is like buying a house or a car or a vacation package: You choose what’s suitable for you. But first, you narrow the field down to the best candidates, and that’s where we can be of help:


Sail Florida Keys in Marathon, Florida, is a good choice for anyone looking to own or charter a sleep-aboard vessel. It offers both American Sailing Association and US Sailing certification, and because some sailors feel that the US Sailing program is a bit more rigorous, this school beefs up its ASA lessons. It also insists that students in its cruising classes know how to sail single-handed just in case.

SFK’s single courses include the three-day Learn to Sail (ASA 101), Coastal Cruising (ASA 103), and Bareboat Cruising (ASA 104, the three you need to qualify for bareboating. Recognizing how busy people are these days, SFK also has four-day combination courses, such as the two-course Combination Basic Keelboat & Coastal Cruising Live-Aboard Class (which covers anchoring, chart reading, and other basic cruising skills) and, for students who already know the basics of sailing, a four-day Combination Coastal & Bareboat Cruising Live-Aboard Class.

But get this: Sail Florida Keys also offers a one-couple-per-boat Basic Keelboat, Coastal Cruising, and Bareboat Cruising combo that takes just six days. Intense? Sure, but school director Bruce Palmenberg notes that this program is even more popular than the nine-day, three-course combo that includes four days and nights aboard a Moorings Beneteau 51.

"The six-day course doesn’t just take less time; it also costs less," says Palmenberg. "The nine-day is ideal for people who want to sail bigger boats, but not everyone wants that."

Blue Water Sailing School(BWSS), often cited for excellence by the American Sailing Association, is based in Fort Lauderdale. Like SFK, BWSS has found that the most popular course of its single- and combo-course offerings is its three-in-one Basic Sailing, Basic Coastal Cruising, and Bareboat Chartering combination.

Winch Students live aboard the boats and, depending upon the course level and weather conditions, sail to the Bahamas or to the Keys. There is also a facility in St. Thomas, and another in the Bahamas emphasizes large catamaran sailing. BWSS boats moor at a different spot every night that’s true even for combos that include the Basic Sailing course so students get a real sailing experience as well as lessons.

BWSS’s advanced cruising courses, such as Offshore Passage-Making, are absolutely first rate, so this is a great school for people who plan to do open-water (aka blue water) sailing. The course descriptions used to end with a line guaranteed to inspire daydreams: "The next stop will be to sail around the world on your own boat ." The website uses different wording now, but the dream is the same.

Steve and Doris Colgate’s Offshore Sailing School, the 800-pound gorilla of sailing instruction, has taught more than 100,000 students over the past 42 years. OSS has a fleet of custom-made vessels and a choice of locations, including four in Florida and one in Tortola. It has long offered US Sailing certification, but starting this year, it is also offering Royal Yachting Association certification.

Offshore Sailing School features a wide variety of courses and programs at every level, including cruising courses, women’s sessions, and more. The Learn to Sail classes (available in three-, four-, and six-day sessions), in which students sleep at a hotel rather than aboard a boat, are still the most popular here, but combination courses are gaining popularity. The prestigious RYA version of Learn to Sail is called Competent Crew, and it’s a full seven-day program that employs 44- to 51-foot sloops.

When you consider Steve Colgate’s background as an Olympics-level competitor, it’s no surprise that Offshore Sailing School is superb at teaching racing as well as introductory sailing and cruising. The Performance Sailing and Performance Racing Week programs are perennial favorites.

Sailingclass Bitter End Yacht Club was my choice for sailing lessons, because the school at this British Virgin Islands resort focuses on day-sailing. In other words, I didn’t need the skills or certification that would enable me to own or charter a sleep-aboard vessel; I needed to improve my skills at daysailing small (less than 30 feet long) sloops.

The resort has more than 100 watercraft. More, in fact, than there are guestrooms. Although most of the classes employ keelboats, the Bitter End’s fleet also includes plenty of light sportboats, such as Hobie Cats and Lasers, not to mention Windsurfers and motorized dinghies.

The three-hour, complimentary Introduction to Sailing course teaches snippets of physics (if the wind is from the north, how can it be that we’re sailing toward the northwest?) and lingo (a sheet is a rope, not a sail got that?). But I had come for the next stage, a Learn to Sail a Rhodes 19 and Hunter 216 that takes just two days.

Classroom work was minimal; mostly we went out on simple Rhodes 19 sloops with instructors dedicated to teaching practical skills and helping us master them quickly. We took turns rigging the boats, sailing at various points to the wind, tacking and jibing (turning), and retrieving a man overboard–well, a lifejacket overboard. Then we came back to the mooring, left the mooring, came back to the mooring, left the mooring until a certain party was confident he could reenter the harbor without triggering a lawsuit.

On Day Two we traded up to a fast Hunter 216, sailed through a gap in the reef and out into open water, fine-tuned our skills, and did a victory lap around Richard Branson’s Necker Island retreat. And that was that. The course was over, and our instructor assured us that we could and should take out one of the Bitter End’s (expensive) sloops.

So three of us graduates headed out the next day, and even I, someone who’d thought he knew how to sail, sailed better than ever before. A sudden squall didn’t faze us, either; we got back to the marina smoothly and safely. And, when we reached our mooring, I made a perfect landing.


Sail Florida Keys Live-aboard courses are all-inclusive. Rates per couple will go up starting Jan. 2; meanwhile (through Jan. 1) the four-day Combination Basic Keelboat & Coastal Cruising Live Aboard Class costs $1,999; the six-day, three-course combo costs $2,999; and the nine-day, three-course combo is $5,499. 305-289-9519.

Blue Water Sailing School Live-aboard courses are all-inclusive. The seven-night three-course combo that concludes with Bareboat Chartering certification costs $1,595 per person. The 14-day Offshore Passage-Making program is $3,495 per person. Note that BWSS does not raise its rates during Christmas week. 800-255-1840.

Steve and Doris Colgate’s Offshore Sailing School The popular Learn to Sail course starts at $895 plus hotel and meals, Royal Yachting Association courses start at $3,595, and Race Week(s), $2,794. 800.221.4326.

Bitter End Yacht Club Accommodations run from $630 per couple per night through Dec. 21 and $1,200 Dec. 22-Jan. 2, 2008. All rates include the Introduction to Sailing course as well as hotel room, three (very good) meals daily, use of the fleet, and many other resort activities. The Learn to Sail a Rhodes 19 and Hunter 216 course described in this story costs guests an additional $75. 800-872-2392.


Sailing does not have to break the bank. Craigslist, eBay, and other sites offer thousands of used day-sailers and live-aboard vessels. Also, local sailing schools and clubs either rent boats for as little as $30 an hour, or sell memberships that let you borrow boats without having to maintain them. Schools and clubs sponsor races, too, and often nonmembers are welcome to crew. Finally, once you’ve earned the right credentials, you can charter (rent) a two-couple bareboat (a live-aboard vessel) in the Caribbean for as little as $3,000 a week.



Editor, scrivener, and magazine doctor Ed Wetschler has written for The New York Times, Delta Sky, Caribbean Travel & Life, Arthur Frommer’s Budget Travel, and other national publications. He is the former editor-in-chief of Diversion magazine and consulting editor for Caribbean Escapes.

Previous post


Next post

The Interview: Toni Neubauer