Southern Learning


Why heading south this winter for a sailing course might be right for you  (published August 2013)

Having taught everything from Learn to Sail to Race Weeks to Offshore Passagemaking classes in beautiful southern locales, one theme—besides sailing—typically appears: students aren’t just there to learn, they’re on vacation.

Over the past few decades, learning to sail has shifted from people’s home waters to places around the world. And most of those places happen to be popular vacation destinations. It is no surprise really, as sailing in tropical isles makes for the perfect getaway. The sun, sand, water and weather all combine to give sailing students a relaxing and rewarding learning experience.

So, in the spirit of getting away this winter, here is a rundown on why and how choosing a learning vacation may be the right choice for you or your family.

Because many sailing schools are based at welcoming resorts, choosing to take a sailing class with your family while on vacation just makes sense. And if the resort route isn’t your family’s style, then a live aboard sailing class might be the perfect way to become charter ready for your next vacation.

It used to be that just Dad was the one who knew how to sail and would suggest loudly (yell) what should be done while aboard. That never worked and it still doesn’t. By taking a sailing class as a family, each person is empowered by learning to steer, trim lines, perform crew overboard maneuvers, navigate and even dock the boat in a friendly atmosphere. Plus, learning to sail as a family will put everyone on equal footing when you sail on your own boat or take a charter, which will make the whole experience more enjoyable.

Somewhere between the BVI and St. Martin I was on watch with two students teaching them about constellations and steering with the stars. At some point we started talking about our different sailing experiences and the one student mentioned that he had done an absurd amount of charters and that he was taking the course merely to try something more challenging for this vacation. And that is just it, taking a sailing class in the Caribbean, Bahamas, Mexico, California or Florida is a great way to do something that is off the well-beaten charter path and allows you to gain some knowledge and experience at the same time. He ended up really enjoying the class and went on to the highest levels of certification.

Let’s be honest. Not everyone wants to spend their vacation living on a boat. When some people think of vacationing, they think of a resort with beaches, pools, restaurants and entertainment. Well, part of that entertainment can be a sailing class.

By taking a sailing class at or near a resort you can have the best of both worlds. At many sailing schools you don’t have to take a full day, weekend, or weeklong class. Instead, you can choose to take a two to four hour refresher course that will help hone your skills and be a fun activity as well. Also, some schools will charter their boats for a day or a few hours if all you want to do is get in some sailing time.

Another great option is to go to a sailing oriented resort that can put you on the water as little or often as you like while you’re there. Resorts such as the Bitter End Yacht Club in the BVI give you full access to boats, host mini regattas and offer sailing instruction.

During student introductions on the first day of class, more than a few students have told me they are “experienced” and don’t need to be there but are there for a spouse or family member to learn. That is all well and good, but the majority of the time that same person will finish the class by saying something to the affect of, “Wow, I didn’t realize how much I didn’t know.” That sentiment is one of the great things about sailing and sailing instruction. There is always something to learn and sailing instructors have different styles, stories and tips that aid in your learning—no matter what experience level you’re at.

This is compounded when that experienced sailor gets off their own boat and is put in unfamiliar situations; like on a live aboard, passagemaking or expedition course. Getting out of your comfort zone is key to learning anything and taking a sailing class outside your home waters may be the way best way to get out and enhance your sailing knowledge.

Another great reason for an experienced sailor to take a class is if they want to move up to bigger boats or catamarans. Operating a 50-foot boat can be quite a bit more intimidating than a 30-footer and many charter companies require some experience before chartering a catamaran. A class in big boat sailing might be what you need to take that next step.

A few years ago while working the Strictly Sail Chicago boat show, the wind chill was a brisk negative 28 and the snow relentless. I couldn’t wait to get back to Florida and the Caribbean and the other show-goers were no different. Though the weather was doing little favors, it did help the charter companies and sailing schools capitalize with sunny photos of swimsuit-clad people sailing through the tropics.

While the main reason to fly south for a sailing course in the winter may be to escape harsh winter weather, it is also a great opportunity to keep your sailing skills sharp or to obtain new ones before the northern sailing season begins. Also, taking a warm weather sailing course before launching your own boat is a great way to energize you for your own summer sailing plans.

No matter why you choose to head south for a sailing course this winter, you won’t regret it. There are a lot of great schools and instructors in beautiful locations who are there to help you get the most out of your experience. Happy learning.

There are hundreds of sailing schools in North America and the Caribbean, so when you start looking for schools in warm climates you need to start with the two major certification organizations where you will find the complete school listings. Or you can get involved with a Sailtime fractional sailing program.

U.S. Sailing:  U.S. Sailing is the governing body for the sport of sailing and has an excellent certification program used by many of the biggest and most respected sailing schools. A good place to start is on the new Start Sailing website at where you will find a complete list of the U.S. Sailing certified schools.
If you go to the main U.S. Sailing website you will find even more information on schools and the curriculum. There are nine certified schools in California, four in the Caribbean and 16 in Florida.

U.S. Sailing also works with hundreds of community sailing programs across America and you can find a list of these schools on the main website. If you join your local community sailing program, in most cases you can be a guest member at centers in other states, like Florida or California where it is warm in January.
American Sailing Association: ASA is a for profit sailing school certification company that has hundreds of member schools  that use the well proven ASA curriculum. You can start as a total beginner and in a matter of a year or two become a seasoned skipper through the ASA program. Looking for a school in a warm place, well there are 36 ASA affiliated schools in Florida and 16 in the Caribbean. Check out ASA at

Fractional Sailing: Sailtime is the largest fractional sailing program with bases scattered across America. If you become a Sailtime member, which gives you access to boats in your home waters and often to sailing lessons, you also qualify for guest memberships at schools in the warm states, too. Sailtime has five bases in California and three in Florida. Log on to