How To Choose a Good Sailing School

, How To Choose a Good Sailing School

Determining what questions to ask before choosing a sailing school when you don’t even know what to ask can be overwhelming. Here’s a start to what questions you should ask, and a bit about what you should hear.

, How To Choose a Good Sailing School

In No Particular Order

There are a lot of considerations when choosing a sailing school. You’re about to invest a lot of money in your learning and experience, so you want to make sure you not only enjoy the process, but also get the most out of it.

I’m going to present considerations to give you an idea of what questions to ask a prospective training facility. These questions probably will inspire more questions that are applicable to your particular situation. Enjoy!

, How To Choose a Good Sailing School

Age of Boats

The age of the boats a sailing school uses for classes may or may not matter to you. While an older boat may be just as well-maintained and maybe even more seaworthy than a newer boat; it might make a difference to you anyway.

If you are planning to rent a charter boat in the islands, it might work in your favor to gain experience on a boat similar to one you plan to rent. Rental fleets usually are populated by more recent models of boats.

Sailing is sailing, and it’s all about the wind, however, if you want to become even more familiar with the type boat you are going to purchase or rent, keep this in mind.

Pay attention to what type and size of boats are available, the maintenance and condition, the safety features and equipment, and even the surrounding marina – that will tell you a lot about the company.

, How To Choose a Good Sailing School

Size of Boats

Ask if your class will be on a small keelboat or larger boat. The debate on whether or not you must learn to sail first with a tiller, then move up to a wheel rages on eternally.

What does matter is which method you prefer. While some prospective sailors may want to jump straight to larger boats with full keels and wheels, other prefer to start “at the beginning.”

Often ASA and US Sailing schools begin classes on smaller, mid-20 footers. They usually have tillers, they heel, they do not have protection from the sun and wind, and may have outboard engines.

I believe you can learn on large or small boats equally well. The theory is the same. One drawback of learning on a larger boat is attempting to understand all the sailing and the systems at one time.

That means a benefit of learning on a smaller boat is being able to concentrate solely on the sailing portion of sailing, leaving the details of engines, holding tanks, windlasses, and all that for later.

, How To Choose a Good Sailing School

Class Curriculum

While learning from a friend certainly has its merits, there is something reassuring about learning when there is a set curriculum. Having a standardized set of skills, maneuvers, knots, terminology, and more ensures you are learning in a methodical manner.

This also is a benefit over being self-taught. While your friend may not quiz you mercilessly on the items they don’t care to emphasize, a sailing school with a set curriculum will check off skills as you learn and demonstrate them. That means no skipping docking practice or safety drills and manuevers…

A set lesson plan also means that when you go to another location to rent a boat or continue classes, that company knows exactly what you have accomplished, mastered, and still need to learn.

Another important consideration is how much time you will spend on the water and in the classroom. While I prefer to use the boat as my classroom – other instructors like to do a bit of white board instruction before heading out. Determine your expectations, and inquire about time on the water.

, How To Choose a Good Sailing School


More than just knowing how much you are going to pay, you also need to know of any additional costs. Keep in mind, a higher price point will probably preclude people not very dedicated to their learning – which benefits you by weeding out anyone not serious about the class.

Amazingly, in one of my recent sailing classes, one of the students had completed a class with a private individual. He had been required to bring his own personal flotation device and a whistle! I had never heard of this.

Factors such as price of class, return on your investment measured in quality of instruction, condition of vessels, and all the other factors listed here all contribute to the worthiness of your expense.

Additional expenses for hotel, meals, fuel, travel, and so on should be added to your total expense to weigh your best options.

If a company says they can give you a discount for combination classes, that may or may not be in your best interest. Keep reading!

, How To Choose a Good Sailing School

Length of Class

I would have to say – the longer, the better! The more time you have at the wheel, over a longer period of time, the better.

Rushing to complete a sailing class does not actually work all that well for beginners. Some sailing schools will offer combination classes. That works out great for people who already have experience and are simply “ticking that box” in order to charter somewhere.

For someone just starting, an abbreviated class does them no favors. Also, combining two levels of classes means you do not have time between classes to perfect the beginning techniques before moving on to the advanced maneuvers.

, How To Choose a Good Sailing School

Number of Students in Class

Three. I swear, it’s three. Or four.

With one or two people, you would think that means more wheel or tiller time, which means more time for you to steer, which equals more yield. Not necessarily.

Part of learning to sail requires observing and letting the knowledge “sink in.” You need time to process what you are learning, and to confirm your technique.

When you are the only person in class, you are busy the whole time. You never have time to watch someone else. Watching someone else gives you a chance to see what they are doing well, and that you could improve. It also reinforces what you have mastered, and you can see their shortcomings, further reinforcing your knowledge.

With one student, the instructor does half the work. You lose out on being able to observe. You have no comparison whether you are doing something really well or just passably.

With two students, it’s much the same. You are working and doing the whole time, with no breaks.

With three students, it’s just about perfect. One steering, one on the main, one on the jib. With everyone rotating, each student gets a chance to see how someone else runs each line, and handles the helm. A lot of learning is comparing what works well and what does not and adjusting technique.

Four students is just about perfect too. One on each jib sheet, one on the main, and one on the helm. If anyone doubles up jobs, then one is the “idler” who can serve as lookout as well as absorb the overall scene.

, How To Choose a Good Sailing School

Practice Opportunities

One important aspect of learning how to sail is slowly reinforcing learning and gaining more sea time between classes.

Some sailing schools have crew programs where you can join a club of sorts, and have the opportunity to get on boats, sail, and solidify what you learned in the last class before moving on to the next step.

These crew programs allow you to build experience, meet other sailors, and build some time less expensively than purchasing a boat.

, How To Choose a Good Sailing School

All Female Classes

Some women call and request all female classes. Good instructors don’t mind mixed or single-sex classes. We teach no matter what, and are pretty good at eliminating the problem of overbearing spouses.

However, some female students prefer to participate in a class of all women. If that’s important to you, be sure to let them know.

, How To Choose a Good Sailing School

Female Instructor

Often, at the school where I teach, people call asking for a female instructor.

Sometimes they are calling for themselves, other times for their wife. If this is important to you, you need to tell the prospective school up front and early so they can schedule your class with a female captain.

, How To Choose a Good Sailing School


When you are spending hundreds of dollars for a class, it’s a good idea to research some reviews.

American Sailing Association, ASA, has their annual Outstanding ASA Sailing Instructor awards. These awards are based on positive reviews from sailing school students. I’ve been fortunate to have been a Featured Instructor, then again a Featured Instructor, as well as an Outstanding Instructor of the Year. I can tell you, it takes a lot of hard work to achieve that recognition, and I’m not the only one at our school who earned those distinctions!

, How To Choose a Good Sailing School

Course Levels and Specialty Courses

Another consideration is if you will want to continue courses with a particular sailing school. Find out what levels of courses they offer.

The benefit would be taking additional courses from a known school, familiarity with their boats and captains and the area. Or, you might prefer to gain experience in a different setting and opt for that.

If specific courses are of interest to you – say docking, or navigation – check to see which courses are offered.

Ask about private classes, couples classes, weekend and weekday schedules, and holiday practices. Some schools will not conduct class on busy holiday weekends due to added stress of crowded waterways.

, How To Choose a Good Sailing School

Credentialing Body

If you are planning on renting a boat elsewhere, the credentials you earn in a sailing class might matter to you. ASA and US Sailing offer internationally-recognized certifications.

This means they have met nationally-recognized standards, have trained instructors, safe equipment, and and complete curriculum. Other schools around the country will recognize your certifications, and you can take different levels in different locations to gain further experience.

, How To Choose a Good Sailing School

Captain Qualifications

Also, find out what certifications the captains possess. Some skippers have instructor trainings and instructor certifications, others are US Coast Guard-licensed captains of varying tonnage in addition to their teaching credentials.

An anomaly, I happen to hold a master’s degree in teaching adult learners – very handy in sailing school! You never know what special qualifications each captain may possess until you ask or research further.

With websites capable of presenting loads of information, you might be able to see the teaching staff, their resumes and biographies online. Then, go meet them in person!

, How To Choose a Good Sailing School

Local Experience

Different sailing school locations yield various experiences. Some are land-locked on lakes; others have access to the ocean. I like to tell students in our classes that we have everything but locks – we have inland waterway, inland marking system, ocean, inlet, bridges, sandbars, intersections, strong tides, ripping currents, and more.

The features of the area in which you are considering taking sailing lessons do matter. Depending on your future goals, you can gain a lot of exposure to a variety of conditions – or not.

, How To Choose a Good Sailing School

The Business

A sailing school is not just a sailing school – it’s a business. Pay attention to rate of return on phone calls and emails, familiarity of office people with their boats and courses. Whatever is important to you, pay attention to those aspects.

If you prefer to conduct business with a company that is environmentally friendly, take note of their practices. You can easily discover if they prefer to avoid single-use plastics, or recycle, or promote ocean-friendly sunscreen.

You might opt for a couple hour charter to get a feel for a particular company if you know you are going to be sailing with them often.

, How To Choose a Good Sailing School

Refunds, Cancellations

It’s better to know in advance a school’s policy on refunds and cancellations. Do understand that last-minute cancellations are difficult due to boats and captains being reserved and scheduled. Unlike cancelling a flight at the last minute; there probably is not someone on standby.

, How To Choose a Good Sailing School

What Else to Ask

What to wear – don’t forget to ask the locals, since they have a good idea of what weather to expect on any day of the year.

, How To Choose a Good Sailing School


Find out what other events the sailing school hosts or in which they participate. One school may be heavily involved in racing, another in working with charity events. Some offer social events for meeting other sailors, or women-specific workshops.

Some schools have skills workshops, or other opportunities. Unless you ask, you might not know, and if you ask and they don’t have it – you might inspire them to add your interest, like waterway cleanups or bird watching.

, How To Choose a Good Sailing School

Yacht Club Sailing Classes

Our local yacht club offers extremely inexpensive sailing classes for adults, to prepare their members to utilize their small boat fleet. This can be a wonderful start for someone new to boating.

Our yacht club teaches on sailing dinghies. This may or may not interest new sailors. Some limitations are the inability to bring along friends who are not members, and not actually earning a certification that translates to the ability to rent a boat in the islands. Instructors may not be actual captains, and you might get wet – however, it’s a great start for beginners.

, How To Choose a Good Sailing School

Self Taught

There are thousands of self-taught people! There’s absolutely nothing wrong with being self-taught. These days, many people have less time, and want to take lessons and learn faster without learning from bad experiences.

Here’s my quote of the year from someone explaining her partner’s artwork: “Some of David’s oil paintings (possibly proof that the man who is self-taught has been to the worst school in the world).” India Hicks.

I’m not sure being self taught is more or less valuable than learning in a class from a reputable school. But, that’s a topic for another article, linked below!

Whatever you do, get started! Go, learn to sail!

, How To Choose a Good Sailing School

What to Read Next

Advanced First Aid Afloat by Peter Eastman is a pretty serious handbook if you are planning offshore and crossings.

Why You Should Take Sailing Classes From A Recognized School – my article giving you some reasons why credentialed schools are best.

Already know how to sail and need to rent a boat? Or you haven’t learned yet, and want to rent one with a captain? Finding a Boat to Rent // There’s an App for That Too // Boat Rental Apps

For both of us, if you use my discount code “KIMWA1,” we both get $100 off our next boat rental at Sailo! Yippee!

Stream2Sea has generously given me a discount code “DeepWH” for you to use at the checkout at checkout to save 10% on ocean-safe sunscreens as well as hand sanitizer, eco stick sunscreen, shampoo, conditioner, sting relief, and UPF clothing.

Updated March 12, 2021


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