Please review the following questions:

  1. Would you rather be onboard or toiling away on a keyboard?
  2. Would you rather be pushed around by the wind or your boss?
  3. Do you prefer Monday blues or Caribbean blues?
  4. Would you rather punch a time sheet or release the main sheet?
  5. Which sounds better: complaining at the water cooler or contemplating life on the cool, clear water?

Do we even need to go over the answers?

Face it, the corporate rat race is not a regatta. It is a grind.  The real question is, how to make sailing a part of your life, even if it is just for week-long getaways. It is easier than you think and it starts with getting the right certification.

The good news is that there are hundreds of sailing schools in the United States that offer the American Sailing Association (ASA) courses covering the basics of sailing and bareboat chartering.  The really good news is that, while there is a little “classroom” learning, most of the education is hands-on, on the water, making it seem less like school and more like the best choice you’ve ever made.

Upon successful completion of the ASA 101, 103, and 104 courses (no, there is no 102, and no, we don’t know why) you will be able to charter and skipper your own boat for daytime sailing. In Europe, you would refer to the Royal Yachting Association (RYA) for a Day Skipper certification. Once you are hooked, you can sign up for additional courses for overnight chartering if your destination dreams extend beyond line-of-sight sailing.

When we first started sailing, after quite a bit of research, my husband landed on the courses offered by Sunsail in the beautiful British Virgin Islands. We signed up with another couple for a ten-day plan covering all three courses, which was a great, convenient way to tackle getting the certification we needed. But if you don’t have ten days in a row, or if you want to take ASA 101 in one spot and 103/104 in another, that works too.

So, what are these courses about? What will you learn? Probably best to let ASA speak for themselves with a little editorial commentary. The courses and “official” ASA definitions – straight from the ASA website – are below.

ASA 101, Basic Keelboat Sailing

ASA Definition: Able to skipper a sloop-rigged keelboat of approximately 20 to 27 feet in length by day in light to moderate winds (up to 15 knots) and sea conditions. Knowledge of basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards. Auxiliary power operation is not required.

This class (2 to 3 days) offers the true sailing basics, and typically you will be on a boat with a tiller for steering versus a wheel. This is great and necessary practice for learning how the rudder works and the foundational mechanics of sailing. I had never been on a sailboat before this class, and I was thrilled to find out that I didn’t need to have a background at all. They teach you everything from the ground up, and this class is all about the basics.

ASA 103, Basic Coastal Cruising

ASA Definition: Able to skipper a sloop-rigged auxiliary powered (inboard or outboard engine) keelboat of approximately 25 to 35 feet length by day in moderate winds (up to 20 knots) and sea conditions. Knowledge of cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather interpretation, safety and seamanship.

I’ll be honest, ASA 103 and ASA 104 sort of blended together for me because we were living aboard the boat for both, and each day we would have lessons and then would practice skills and sail to our next destination. I suppose 103 was probably more about extending our bank of basic skills and 104 layered on additional new concepts like charting. What was most beneficial was being able to learn a skill and then be able to build on it with additional skills and gain the necessary practice to really understand what we were learning.

ASA 104, Bareboat Cruising

ASA Definition: Able to skipper a sloop-rigged, auxiliary powered keelboat of approximately 30 to 45 feet in length during a multi-day cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions. Knowledge of provisioning, galley operations, boat systems, auxiliary engine operation, routine maintenance procedures, advanced sail trim, coastal navigation including basic chart plotting and GPS operation, multiple-anchor mooring, docking, health & safety, emergency operations, weather interpretation, and dinghy/tender operation.

Don’t worry if reading those definitions doesn’t mean much right now. I remember reading those definitions when we signed up and having a sense of dread that was exceeded perhaps only by my sense of confusion.

When I look back to that moment, I remember I had absolutely no idea what to expect when we signed up, other than I wasn’t going to be very good at it. I am not the most “mechanically inclined”, and if I’m honest with myself, I don’t think anyone would consider me a particularly adept driver on land. How in the world was this going to translate on the water?

Knowing that it was going to be me, an instructor, and three very capable and skilled firefighters on the boat, I read the text book ahead of time and, in secret, bought Sailing for Dummies and a DVD on sailing basics. None of this was helpful. It was like reading Greek, and I ultimately went into the experience understanding nothing at all except that I was probably going to accidentally capsize the boat.

The good news is that all I really needed was a point of reference. I need to see it, do it, and understand why I was doing it. Over the ten-day course, that’s exactly what happened. I did earn my certification but more importantly I gained a love of sailing where I never thought I would.

Sold? I thought so. Here’s what you need to know before you go…

  1. It is ok to know nothing when you arrive.

This is school, there are tests, and you need to pass those tests to get your certification. In sailing school your goal is to learn and demonstrate knowledge of basic sailing skills, rules, safety, and boat care.  That said, do not stress out like I did! I promise, you will learn everything you need to know on the water and in the short instructional sessions. Just pay attention, ask questions, study when given the opportunity, and relax!

If you just can’t wait to dive into the material, the ASA has a great free online sailing course that can help get you started (click here). You should also check out their website and have a look around. We love the information and support offered by the ASA. They are a terrific resource for sailors of any experience level.

  1. Pack light. Then remove 50% of those items.

I had never sailed before so greatly overestimated cabin space for my cute dresses and matching sandals for the evenings, multiple shorts/shirts combinations, long shirts and pants just in case, and bathing suits galore. I also brought approximately a pound of face lotion, makeup, and other unnecessary items. Don’t do this. Plan to wear items more than once and focus on essentials. You probably need fewer clothes than you think but will definitely want to include items like a headlamp, boat-friendly shoes to avoid slipping, and a good hat with a string or clip. Check out our what to pack blog for more Intel.

  1. Not all instructors are created equal so do your research.

By a stroke of luck we landed the best sailing instructor ever, Matt Holt with Sunsail in Tortola. Legitimately, look him up, he’s earned all kinds of sailing instructor accolades. I often tell people that he is the best teacher I’ve ever had in any subject: Incredibly skilled and knowledgeable but also very good at teaching and explaining new concepts. In addition to Sunsail, there are many other companies in the U.S. and abroad with excellent instructors, and as you research these companies pay attention to details. It is important to research the company you will be signing up with, read the reviews, and if it is a deal that seems “too good to be true”, like most things, I’ll bet it is.

  1. Have an organized way to take and keep notes.

I may not be good at mechanically-based activities, but I am an excellent student! I have the grades and rousing Friday-night-at-the-library collegiate stories to prove it. Because of this, I am particularly well suited to give the advice that you bring a notebook for taking notes that will serve you not only for test taking, but in the future when you charter on you own. There is a lot of material, and much of it will seem foreign in nature. The better notes you can take for yourself as an on-board resource, the more well-equipped you will be when you put the sail up for the first time, anchor for the first time, or wonder who has the right of way.

  1. Embrace the unknown and the unexpected.

If you’ve never slept on a boat and you sleep “head in” you are going to hit your head every single time you get up. If you turn 180 degrees with your “head toward the door”, you will hit your head every other time. You are going to hit your head. But it’s ok! That’s just part of the sailing lesson. You may also have severe weather that changes your plans, or you just might not “get” knot tying. But for every small frustration, there are many, many incredible experiences just around the corner: learning new skills every day, snorkeling, exploring beautiful islands that you can only reach by boat, and the special camaraderie that only comes with accomplishing something entirely new as a team.