How to become a sailing skipper

Want to learn how to sail?

Carving through clear water, harnessing nature, under a blue sky: sailing is a dream for many of us. It represents freedom and a connection with nature that is sorely missed in this day of commuting and social media.

“…it is an interesting biological fact that all of us have in our veins the exact same percentage of salt in our blood that exists in the ocean, and, therefore, we have salt in our blood, in our sweat, in our tears. We are tied to the ocean. And when we go back to the sea — whether it is to sail or to watch it — we are going back from whence we came.” — John F. Kennedy

If you are thinking about sailing, you need to answer the “where”, the “who”, the “what” and the “which”. That is, where should I learn to sail? And who is the best to teach me how to sail? Then, what sailing course should I do? Finally, which qualification is important to have? In this post we explore the best places to sail in the world, then focus in on the best sailing schools in those places. We take a brief look at the courses you can do. Then we look at the sort of sailing qualification that will benefit you the most.

Where to sail

When looking for the best places to learn to sail you need to weigh up a few factors. Proximity is important as the closer the location, the quicker and cheaper it will most likely be to visit. In the table below we have listed proximity relative to someone coming from the United States and Canada (where the bulk of our readers live). Warmth is next. If you’re like us you enjoy sailing when it is warm. For our star rating we have looked at how warm the place is over a twelve month period. Our third factor is Beauty. Here we focus on the natural beauty of the place in question. Finally we look at quality of Sailing Schools. This takes into account availability of a broad set of sailing conditions, recommendations on Tripadvisor and subjective elements.

The list above shows that all things considered, sailing in the Virgin Islands is the best option for most people living in the United States and Canada. The Virgin Islands provide consistently good sailing conditions for most of the year, excepting 2–3 months in the middle of summer (July-September). Most other places are the other way around: they provide decent conditions for 2–3 months of the year; outside of which they are less than suitable. Want to find somewhere to sail when it is zero degrees and snowing outside your home? The Virgin Islands’ “Christmas Trade-winds” are legendary for their consistency. And it rarely falls below 80º Fahrenheit there. Ever.

Who to learn to sail with

Given that for most of our readers the Virgin Islands is — all things considered — the best place to be sailing, we will now focus in on sailing schools in the Virgin Islands. We note that there are actually three separate “groups” of Virgin Islands: the British Virgin Islands, the US Virgin Islands and the Spanish Virgin Islands. The most famous of the three, and the group with the most options for sailors, is the British Virgin Islands. So we narrow our focus further to schools located here.

In looking for a sailing school we believe the most effective measure is reviews from recent past clients. So we have taken a snapshot of the three major review sites: Tripadvisor, Google and Facebook. Given that recency of reviews is key, we have looked at five star reviews that have been given over the past six months.

Sailing Virgins is the clear winner based on recent user feedback. This company is a relative newcomer to sailing schools in the area. Founded by Australian sailor James Kell early in 2016, we asked him what he is doing differently to his competitors. “…Sailing Virgins started when a few of us wanted to reach out to people in their 20s and 30s who want to improve their sailing. We saw that sailing is changing so much, yet these people were being ignored. We all come from working for this phenomenon called The Yacht Week so we know the sort of energy that comes when energetic, positive people go sailing. That’s why we started Sailing Virgins”. Judging by the reviews this strategy seems to be working for them.

Which Sailing Course to Book

The next question is how many different courses are there on offer and which one is the right one to do? Fortunately this decision is made a lot easier by a select few schools. We found a highly regarded school in the US Virgin Islands, on the island of St Thomas, Virgin Islands Sailing School (VISS, ), which focuses on catamaran instruction.

There we asked principal Scott Dempster what type of courses he had on offer; “…we like to keep things simple. Our courses all go for one week in duration. If you are a beginner we have a one week course for you. If you have sailed before we have a slightly more intense week-long course for you”.

Back over at the British Virgin Islands, Sailing Virgins offers similar packages. Says Kell, “…when establishing our courses we saw what Virgin Islands Sailing School were doing and liked it a lot. So we emulated them. All our courses start on a Sunday and end on the following Saturday. We have three levels, beginner, intermediate and advanced. Our most popular level is the intermediate as this gives the successful student a qualification to charter their own boat”.

On this post covering how to sail, we have established where to sail, who to sail with and now what sort of course to book. Let’s continue on to look at the outcomes of such a course, including the qualifications a student is likely to earn.

Which qualifications are most beneficial

Most people learn to sail for one of two reasons: one, so they can eventually go out sailing with their friends of family. Or two, so they can work in the industry. That is, they want to gain the skills necessary to sail their own boat. The first organisation to offer such qualifications was the Royal Yachting Association out of the UK. They are still held in high regard amongst sailors. However nowadays there are other associations that also offer a very comprehensive syllabus. In the US and Canada you have the American Sailing Association (ASA), NauticEd, Sail Canada and International Yacht Training (IYT). While a qualification from any of these is seen to be perfectly adequate, some offer a few more benefits than others.

The organisations listed above are all held in high regard amongst both sailors and charter companies worldwide. However tech-based NauticEd ( takes a different approach, focusing on what the charter companies ask for: the sailing resume. All courses on NauticEd are done online, including the logbook. When a charter company asks for your sailing resume, rather than having to transcribe your paper logbook, with NauticEd it is simply a case of printing out your most current resume. This is pretty handy.

Nevertheless it must be noted that the exact star-rating is a general guide only. If anyone is seeking a world-renowned Yachtmaster for working in the industry, they would do well to look at an RYA qualification. NauticEd has partnered up with the RYA to be able to offer RYA theory courses and qualifications through its own program. This may be the best of both worlds.

The American Sailing Association is very well known in the United States. It was the first organisation to offer a specialised catamaran skipper endorsement, teaching the ins and outs of catamarans.

In summary the organisation you choose to gain your qualification from is not as important as the school you choose to teach you. We would recommend choosing whichever was most suitable to your lifestyle: some people favour a tactile text-book based learning approach whereas for others they prefer everything to be online and/or on their devices.

Best ways to get to the Virgin Islands

The easiest way to get to the Virgin Islands is to fly to St Thomas (STT) and ferry to your island of choice. STT offers daily non-stop (direct) flights from several east-coast hubs including Atlanta, Baltimore, Boston, Charlotte, Chicago, Detroit, Fort Lauderdale, Miami, New York, Newark and Philadelphia. If you come from the west coast or would simply like to spend a day or two in Puerto Rico on your way through, connecting flights are available to and from Atlanta, Dallas, Los Angeles, Miami and New York via the San Juan hub. Check out startup Fareness ( for time-based flight deals.

Once you reach St Thomas airport, a ten minute, $10 taxi will take you to the Charlotte Amalie ferry terminal. From the ferry terminal you can catch a $40 ferry to the British Virgin Islands. The main two ferry terminals in the main British Virgin Island of Tortola are Road Town and West End. West End is the home of both Sailing Virgins and Tortola Sailing School, making connections simpler for these two schools. Road Town is closer to Sunsail and Rob Swain Sailing Schools.

Best time of the year to do a sailing course

The sailing season in the Virgin Islands is active for around nine months of the year. Longer if you don’t have a problem sailing during the hurricane season (which is not as crazy as it sounds. However trip cancellation insurance, always recommended, is a must in this case). The wind, always decent because of the trade-winds, tends to be the best around December and January. However this is also when the crowds are the highest. Choosing a shoulder season period such as November or May can be wise if you would like to avoid the crowds. However if you like the festive atmosphere created by lots of people, it’s hard to miss the Christmas/New Year period.

What to bring on a sailing course

Whichever sailing school you choose will help you in this regard. In short, you don’t need to bring much with you. In fact most, if not all schools recommend a “less is more” approach. Given you are in the Virgin Islands, you won’t be needing any heavy foul-weather gear. A rain jacket suffices. And then it’s simply shorts, shirts, skirts and swimwear. Even shoes are an option when sailing in the Caribbean. While some sailors swear by gloves, and they are necessary in cold weather sailing, it is hard to find a sailor in the Virgin Islands who uses them (with the exception of when they are racing).

What to read before a course

The sailing school you choose will either point you to a place to buy the relevant text-books or if you are doing a NauticEd course, will send you the login details for you to get straight into your course. If you are interested in general sailing literature to give you a taste of things, we have read and can recommend the following:

A Voyage for Mad Men: The incredible true story of the first solo round-the-world race, held in the late 1960’s. Nine yachts started. Only one finished.

The Long Way: French sailor Bernard Moitessier’s account of the same race, which he “won but didn’t win”. If that is difficult to understand, read one of these books.

Treasure Island: the classic novel by Robert Louis Stevenson, who wrote a tale of pirates and buried gold. The British Virgin Islands feature heavily here.


In summary this article covers the Virgin Islands as the recommended place to sail out of a shortlist of seven well-known sailing locations. As far as schools go, we recommend relative newcomer Sailing Virgins as the highest-ranked school according to five-star ratings over the past six months on platforms Tripadvisor, Google and Facebook. We note the actual sailing association you choose to accredit with is not so important provided it is well known (we feature the main organisations here). Yet we note that NauticEd is recommended for people who wish for a tech-based solution to their sail training. And finally we cover such aspects as how to get to the Virgin Islands, the best time of the year to sail, what to bring and recommended pre-reading material.