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When I stepped off the plane I wasn’t exactly sure what to expect. However, one thing became clear, quite quickly. It was hot. I couldn’t help but wonder why I didn’t make more trips down south from Boston during the rainy and somewhat miserable month of April. I was on my way to the headquarters of the Offshore Sailing School at South Seas Island Resort on Captiva Island, Florida, to take part in a women’s only Fast Track to Cruising course. For women, taught by women—it sounded like just what I needed, and I had jumped at the chance to partake.

As a full-time liveaboard going on my fourth year, who sails frequently and works in the industry, I certainly didn’t feel like a novice. That said, I knew that while my lifestyle, career and passion all revolve around sailing, I still had a lot to learn. I also knew that I didn’t have weeks on end to learn it, especially if I wanted to use my newly gained knowledge this summer. The “fast track” part of the course means that over one week you learn the basics of sailing, and beyond: from how to tie a bowline, and tacking and gybing, to how to plot a course, and actually stay on it, there is no doubt that your sailing knowledge will grow exponentially.

Smiles all around once we got the broken impeller out

Smiles all around once we got the broken impeller out

The course does go by quickly but is by no means rushed, and by the end, you will go home with three US Sailing certifications; Basic Keelboat, Basic Cruising and Bareboat Cruising, after passing the written and practical exams that is. (Pro-Tip: when they recommend that you study beforehand, they mean it; they make that easy, though, providing books and other materials ahead of time.)

Like many women sailors, most of what I already knew had been gained from my much more experienced significant other. During the classes, it was hard not to notice the difference between learning from my partner and learning from a stranger. Let’s just put it this way, I felt much more eager to respond to commands or direction when I wasn’t thinking about how my instructor hadn’t done the dishes in the past three days. I also wanted to go on a women-only trip as an effort to encourage more women to take the initiative and do the same. The feelings of empowerment, independence and confidence that come when you really learn the ins and outs of sailing and how your boat works are second to none. It might sound cheesy, but knowledge really is power.

Barb explains the ins and outs of shore power

Barb explains the ins and outs of shore power

My first two days at sailing school were spent on a Colgate 26 with my, instructor Barb, who has been teaching sailing for over 20 years and flew down from New York City especially for this course, and our two other crewmembers, Adrianna from Columbia and Lisa from Tennessee. The four of us got along flawlessly, which was quite the relief. Considering we would be spending the following week together, including five days aboard our sailboat, appropriately named, Offshore 1, a Jeanneau 439 it was good that we got along—not to mention that teamwork and trust would be two major aspects of the course, as is the case when sailing with crew in just about every situation.

While the women’s courses are typically one boat, one instructor and three students, this time around there were two boats, two instructors and six students. The other instructor, Joelle, who teaches regularly from the South Seas Resort location, and her crew, which consisted of Lisa and “the Kellys,” as we called them, were on a Leopard 48 catamaran and their course was nearly identical to ours, aside from an additional certification specific to catamaran cruising. Having two boats instead of one created a flotilla vibe, which added to the overall experience.

“The Kellys,” came together on one of their every-year-or-so reunions since back when they’d been college roommates, while the rest of us flew solo. However, just like summer camp or your freshman year at university, while we met as strangers we left as family. Each student’s sailing experience varied, but everyone seemed to be at a similar level. Aside from Adrianna from Columbia, everyone was originally from the South (you could say I picked up a little southern twang by the time I left) and of a similar age. Aside from myself, that is, and after we did the math at dinner one night it was discovered that everyone on the trip could have, hypothetically, been my mother. It gave us a good laugh, and not only did I learn a lot about sailing from my instructors, I learned a lot about life from my new friends.

At the resort, our days began with classroom lectures. There were a lot of slides, a lot of white-boarding, a lot of demonstrations on a mini-model sailboat and a lot of questions. These lasted a few hours and were followed by a short break for lunch after which it was straight to the boats, where we were given the basic rundown as to what part of the boat was what. Then it was out on the water. I had never sailed a Colgate 26 before and not only did I feel comfortable and safe, but I had a great time. We got very lucky with the weather, enough wind to keep the sails full but not so much to scare away the beginners.

the catamaran crew shows off its well deserved certificates of completion

the catamaran crew shows off its well-deserved certificates of completion

Before I knew it, we were on Day Two, tacking, gybing and rescuing our man-overboard cushions, all in the company of some of the most beautiful wildlife I’ve ever seen. Full disclosure—I’d never seen a dolphin before, so I was more than a little excited when I saw my first one. Trying to keep me focused, Barb yelled, “Don’t worry, you’re going to see more,” but I didn’t believe her. Little did I know I’d see them every day and everywhere, just another reason why you should always listen to your instructor. Besides dolphins, I was awestruck by the pelicans and manatees. OK, let’s face it, I was even awestruck by the palm trees.

After three nights at the resort (which one of the crew appropriately deemed, “the most luxurious bootcamp ever”) and two days on the Colgates, it was time to move from tiller to wheel and step aboard the “big boats,” which is where all the fun happened. After another morning lecture and a beautiful sail up the Gulf, anchoring was a breeze, and we were ready to enjoy our first night aboard. Having been the only liveaboard on the boat, I was slightly blown away that we went through an entire water tank our first night, at which point our captain made it clear—no more showers. (Which was fine with me, I’m used to it.)

The crew inspects the rig of Offshore 1

The crew inspects the rig of Offshore 1

That wasn’t the only thing that happened our first night at anchor. It was just as I was about to doze off in the cockpit, sleeping outside being one of my favorite parts of warm weather sailing, when I heard a crack of thunder and suddenly it looked like someone had just set-off a fireworks finale. Luckily, I was able to scoot inside before the downpour hit, which was actually a bit refreshing. But then we did a 180 on our anchor and the next thing I knew I was sitting upright again. Meanwhile, in the other bunks, Adrianna had put on her foulweather gear, ready to save the day at any moment, and Lisa was texting her husband for some reassurance. When he asked her what our instructor was doing, she replied, “She’s snoring!” Given that fact, I assumed things were OK. However, I still didn’t close my eyes until the storm had passed.

The next morning there were no casualties, but some other issues arose, such as the dinghy painter getting stuck under the boat while also losing all its air and filling with water. Small problems in the big picture though. Having had plenty of experience living on a mooring with my dinghy as my lifeline, I volunteered to bring her back to life.

With each day that passed, the excitement, experiences and stories to tell when we got home grew. After getting the boat shipshape on the second day of sailing the Jeanneau, we were motoring out through the channel near Cabbage Key when the engine alarm went off: a sound I’m pretty sure nobody likes to hear—ever. Soon it was official; our engine was down for the count, right in the middle of a busy channel. Luckily, everyone was game to sail back to the anchorage without the engine, and I got to live out the dream of anchoring under sail alone. Besides nearly hitting a daymarker, we nailed it.


After some troubleshooting, we discovered that the lid to the strainer had been askew (it was easy to tell there was an issue, as there was no water in it), which led to a busted impeller and a melted waterlift muffler. If there had been a shop-vac to suck out all the broken pieces that broke off the impeller and a spare muffler, we could have fixed the problem ourselves. As it was, we had to resort to some help from the lovely people at Offshore Sailing School.

The last few days were a bit less intense, which was good, as we had time and the right mindset to take quizzes, study, relax and get ready for our tests. We all passed (in the 90s might I add!) and while afterward my brain, forearms, legs and neck were all a bit sore, my spirit had never been higher.


Sailing Teachers

The Offshore Sailing School has grown vastly over the years. As of 2014, founders Steve and Doris Colgate estimated that they had taught over 130,000 students. And if the name Colgate sounds familiar, it should. Both Doris and Steve have played huge roles in expanding the scope of the sailing world and making it accessible to people who may not have had the opportunity otherwise, or were hesitant about giving it a try.

Doris founded the National Women’s Sailing Association (NWSA) back in 1990 as well as the Women’s Sailing Foundation (WSF) in an effort to enhance the lives of women and girls by educating and opening them up to the joys of sailing.

Meanwhile, Steve is the original founder and chairman of the Offshore Sailing School as well as the brains behind the acclaimed Colgate 26.

Offshore Sailing School will be hosting another Women’s Week at South Seas Island Resort ( on its new Jeanneau 479 in November. For more information go to

Photo courtesy of Offshore Sailing School

August 2017



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