Over the years, I’ve met numerous people who have decided they want to get into the sport of sailing, for one reason or another. For some it is perceived as a cool hobby, nautical and yachtie. It encompasses lots of intertwined skills and abilities, from knowing one’s position on a chart, how to tweak boat speed, to turning a wrench on occasion.

For others it is a chance to see the world before it loses its charm as the world continues to get smaller. Not surprising, for many sailors, it may begin as a sport, but it becomes a lifetime passion for which there is no substitute.

Whether I work a booth at a boat show, or simply stroll down the bulkhead along the waterfront, I often hear the conversations of people talking about their interest in this fascinating thing…this sailing thing.

I recall one late-afternoon dinner I had at the Bluewater Bistro on Lake Union at the in-water boat show that kicks off the year (but not the season, at least not in Seattle in January). The booth behind me in the restaurant had four people, talking about the show. One of the guys commented how much he thought he would enjoy the freedom and outdoor activity that sailing seemed to represent. The others were supportive but offered little constructive advice on how he might go about it. When one of them mentioned Annapolis was the sailing capital of the country, I made some comment to downplay that I was eavesdropping on their conversation while we all had a drink to warm up after standing outside in the cold.

We had a pleasant conversation that I hoped added some positive input to what this fellow wanted to learn more about. It would be nice to think I motivated him to get beyond simply wondering and take the first step to see what sailing is all about.

"Is sailing hard?", he asked, with an inquisitive grin. "Not at all", I replied. With the right instructor and the right sailboat, most people can learn to sail by themselves after a few short lessons. Many sailboats today are being designed specifically for solo-sailing with low weight, a self-tacking jib, and easy rigging.

(Below: The Hanse 348  is a great first sailboat for beginners learning to sail. It won 'Boat of the Year' in 2019 when it first debuted.)

hanse 348 sailboat for beginners


How Did You Get Here?

While it is not critical, I find it helpful to understand how someone got interested in sailing, and why the experience got them wondering if it might be something they would enjoy. This can happen in a variety of ways, and knowing the background can help determine the right path to get the necessary experience and training. It helps to know what, when, and where.

Of course, many people get acquainted with sailing because it is part of their family life. With sailing parents, children are very likely to be urged to follow the same path, as it keeps the family together in the unique ways that sailing and camping provide.

For others, it all began in summer camp as a kid. Many camps are situated by a lake or other body of calm water. It is customary to provide the opportunity to get out on the water on canoes, kayaks, Sunfish, Lasers, catboats, Hobie or Nacra cats, or any number of other small boat types. For a kid just learning about the world (and themselves), being in company with new friends and getting out on the water provide the perfect opportunity for magic to happen.

A group of kids decide to venture out from the shore, so counselors launch a couple of small sailboats. Under the watchful eye of counselor or instructor, the kids splash around on the small boats, just having fun. And then one kid suggests they try to reach the other side of the lake and use the sails to make it happen. Even if it is only a hundred yards across, it is still too far to paddle, so they agree to raise the sail and attempt to make it using the power of wind. A puff fills the sail, and they are amazed as they take off in a direction someone notices is directly related to how the tiller is turned. The basic pieces of the puzzle come together, and hopefully at least one of the kids comprehends what is going on. Not only do they reach the other side of the lake, but on the way back they have a bit of a race with the other kids.

A sailor is born.

(Below: A great introductory to sailing video by Youtube channel 'Learn 2Sail'.)

Another first taste of sailing might happen on family vacation in the Caribbean, Mexico, or Hawaii. Many resort hotels contract with a sailing catamaran to take guests out on excursions for a taste of the local waters. Maybe there is a glass bottom in the boat, or maybe it is a large cat that holds dozens of vacationers. The passengers are thrilled to sail at speed along the crystal-clear waters of paradise. Savvy resorts want guests to enjoy the water, and so maintain small catamarans to use off the sandy white beaches. Even a half hour with someone who knows how to sail can be exciting, whizzing by those in lounge chairs along the beach.

Of course, going out briefly on a sailboat does not set one’s life goals any more than taking your first helicopter ride makes you want to become a pilot. But it can open one’s eyes to a new experience. And if it is a pleasant memory, perhaps it will lead to other similar experiences.

I once researched American yacht clubs’ success in their junior sailing programs. Every yacht club has a junior fleet component that teaches and encourages sailing and racing. It is often the first organized sailing program young people are introduced to. While I assumed its contribution at a national level was a significant element in growing sailing among younger people, I found that simply is not true. Relatively speaking, few adults who later become experienced sailors got their introduction and “magic” moment from a junior sailing program.

I ultimately discovered most people who become experienced cruisers got the initial taste of the cruising experience from going sailing with friends and family on other boats. They were part of a sailing and cruising adventure and at some point decided to invest the time and energy to try this for themselves.

In fact, I met few “successful” cruisers who got the sailing bug from a yacht club junior sailing program.

(Below: Check out USSailing.org for information on how to get your kids involved in learning to sail.)

kids learning to sail

In today’s world, one can’t help but notice yet another venue that plays a significant part in drawing people into the sailing world. It is now as important to the sailing industry as any other program, certainly more so than traditional association efforts to grow its base.

This unique medium is found on YouTube, and they are the sailing channels of couples living aboard and cruising the world, while sharing every moment of their experience with the world and their subscribers. The addiction factor of these channels is astounding, as I know many people who would rather watch these weekly episodes of beautiful couples living the dream than anything else. The most popular couples have millions of subscribers, many of whom enroll in Patreon programs to pay to watch each new episode and contribute to the couple’s daily world. The monies they receive are enough to not only pay for their lifestyle but pay for equipment upgrades and even contribute to the purchase of the next boat.

To name a few of the popular channels: Sailing la Vagabonde, Gone with the Wynns, Ruby Rose, Tula’s Endless Summer, Project Atticus, SV Devos, RAN Sailing, Hilda Sailing, Sailing Doodles, and Sailing Zingaro. There are many more. These are incredibly popular and represent a totally new form of entertainment of genuine people living life. No magazine or boat show can ever hope to inspire the sailing lifestyle to this level. Marketing managers were quick to seize the opportunity here and wasted no time providing these couples with the latest dinghy, equipment, and even new boats at one assumes to be smoking deals.

This YouTube phenomenon is truly wonderful. I know dozens of boats sold specifically because the buyers wanted to live the same carefree lifestyle, bikini and all. And surprisingly few that I know have had any previous experience on the water.

The reason I mention the many ways people get interested in sailing is that it often determines what kind of sailing is most appealing. People lusting after the lifestyle of tanned couples catching fish for dinner each night will be more attracted to cruising than someone who first experienced sailing in camp. That kid grew up maybe just wanting to spend time relaxing on the water while learning to explore all corners of the lake under sail. That may be all the motivation there is for now.

(Below: Youtubers Gone Wtih The Wynns reflect on their first year as sailors.)


Take a Class

There are numerous reasons why the best thing to do, once the interest in learning to sail becomes more than a fleeting notion, is to find a reputable sailing school and enroll in a basic sailing course. I say reputable because a singles club masquerading as a sailing school is not likely to advance your understanding of sail theory or practical boat handling. It may be a successful endeavor for other reasons, but that is beyond the scope of this article.

In Annapolis, there is the well-respected J/World, a sailing school using various J Boats for the different layers of sail training. It has turned out many sailors, some of whom go on to excel on the racecourse.

But J/World is but one small school among the possible sailing resources, even with its locations in San Francisco, San Diego, Puerto Vallarta, as well as Annapolis. A quick online search identified numerous performance sailing schools, from Maine to Key West, Seattle to San Diego, Chicago to Galveston. Sponsored or hosted by the American Sailing Association (ASA), U.S. Sailing, and the Offshore Sailing Schools program put on by Steve and Doris Colgate, they focus on essential skills and knowledge to introduce new sailors into the sport.

There is so much to be said about enrolling in a sailboat racing program. While racing may not be yet on your radar screen as an interest (and may never be), a course curriculum that focuses on sail trim and boat performance is going to be better than courses that try to teach basic sailing along with the softer side subjects that detract from what you really need to know about the art of sailing. Anchoring, understanding general maintenance, and navigation are all important subjects, but they are for much later down the road. It is far better to become familiar and experienced in getting the proper trim angle of all headsails and how to get the boat moving well. While tactics are not important if you are not going racing, they relate to handling the boat when you are at the line early and need to slow down, or how to maneuver in close quarters under sail. Only sailboat racing courses provide these opportunities. The rest can come later.

You will learn how to read the wind over the water, and how the forces of wind and waves provide both the power to drive the boat fast as well as to create situations you will need to deal with. Again, racing is about performance, and developing performance skills in sailing is a very worthwhile goal.

(If you're near Anacortes, Washington, don't forget to check out the Seattle Yachts Sailing Academy!)

sailing academy instruction


Your First…At Many Things

The next step after taking one of the sailboat racing classes is to enroll in a multi-day sailing course where you go sailboat cruising. It is still all about the basics, but beyond reading the wind and waves, and covers many topics that are necessary to successfully ease into cruising. One learns the physical side of the activity, using the winches to trim sails, and the other running rigging gear found on most sailboats. You will also build upon the sail trim skills you may have already learned at the racing school, with particular emphasis on short-handed sailing and getting properly trimmed when there are only one or two crew on the boat…unlike the four or more crew on the typical racer.

Docking, line handling, and maneuvering in close quarters are all needed skills to safely enjoy sailing on one’s own. As most cruising boats will likely have a small diesel engine for auxiliary power, learning the basics of engine maintenance and operation is valuable, and there are many follow-up courses offered at boat shows and at more technical levels to delve deeper into such gritty subjects. Personally, I found these courses enlightening and very satisfying as I moved closer to becoming a self-sufficient cruising sailor who knows how to think on the water.

Spending time in the boat’s dinghy, for example, the lessons to be learned can be amazing. I recall capsizing in a large sailboat’s sailing dinghy one weekend. I went from warm and dry to cold and wet in the blink of an eye (and maybe even a little scared from the sudden shock of my miscalculation). It was a tremendously healthy learning experience. Sailing is for real and developing a healthy regard for the power of “the sea” is among the most important lessons one can learn.

Those who grew up sailing small boats in a lake environment may not feel the need to go farther than the basics, as their aspirations may only extend to open boats that serve a very limited use. A daysailer is an open boat, and won’t have a toilet, beds, a galley, or other interior accommodations. Its sole purpose is to provide a platform to go sailing for a short time. An hour or two on a daysailer may be all these folks envision for the foreseeable future. That is totally fine, and there are dozens of small boat choices that offer portability, are easy to launch and store, and provide all the sailing fun one could hope for in the protected waterways where these boats are usually operated.

Unfortunately, those who go the daysailer route will miss out on one of the most cherished memories of sailing: spending one’s first night at anchor on one’s own boat. Reaching a quiet and hopefully protected spot to set the anchor for the night, then cooking dinner and relaxing after a day out on the water, sets the stage for an evening in the stars, eventually going to bed where the boat’s motion will rock one to a sound sleep that some have never experienced before. And if there happens to be a shower or two during the night, the combination of the motion and the sound of rain hitting the deck is all the more magical. The memory of that night will be with you forever.


Taking the Plunge

At some point it will be time to consider looking for and buying your first sailboat. True, there are many who can get by with chartering or borrowing a boat when the opportunity and mood strikes, and that’s fine. Again, if one’s sailing ambitions doesn’t extend beyond a simple daysailer, that is also fine. There are dozens of choices of appropriate daysailers out there. Whether one finds the first boat at a boat show or a garage sale, it doesn’t matter. A little elbow grease can turn even an older fiberglass daysailer into a vessel ready to tackle the world. Let the fun begin!

(Below: Different examples of a daysailer. Photo cred: SAIL Magazine.)

example of daysailer 

For those who want a bit more of an all-around sailboat, no problem. Many people ultimately want more than a minimalist camping experience. They will be better off seeking a boat large enough to have interior accommodation: a head, galley, saloon, and enough berths for the crew. It is not a very big check list. There are many, many suitable boats out there waiting for the first-time buyer. Forget those goofy “experts” who go on about sail rigs, keel choices, and silly things that will mean nothing to a new sailor. If the boat has a tiller, fine. If it has wheel steering, fine. Neither is more important at this stage. Hopefully one will own both over the course of one’s sailing life.

An older boat may offer the right combination of capability and budget, such as a Sea Sprite 23, Catalina 27, or any number of production builders’ entry level sailboats built in the last couple of decades. These builders recognize the importance of providing a lot of boats to the newbie sailor, with hopes they quickly learn the ropes and want to step up in size the next season. In the ideal world, these builders hope to continue selling these sailors their next boat again and again as they live through the boating lifecycle. I know this marketing philosophy works, and I am always impressed when I meet couples who have stayed true to one builder for the last four or five boats. Such a strategy obviously works. (That is also one reason why some sailing schools offer training on one brand of boat that the builder supplies for a very good price. It just makes total sense.)

There are some of us who leapfrog this normal chain of events for specific reasons that preclude following a more traditional path. A desire to race in the Newport-to-Bermuda event might push one to buy a larger boat early on to qualify for entry into this biennial popular event. Or it might be the goal to find a suitable liveaboard boat (which was my case) as I could not afford both a boat and a place to live when I was a young man in Seattle in the 1970s. A cruising sailboat made perfect sense to me, even if I was a bit underqualified to sail a larger boat. But I had friends, I managed, and I learned.

Much as I’ve said that the typical daysailer is limited in its long-term utility, it is also true it is surprisingly easier to sail a larger boat than a smaller one. The small boat will react quicker to changes in trim and balance, providing instant feedback when one does things right or wrong. Conversely, a larger boat is much slower to react, and this is a good thing when learning to sail short-handed and there are so many things to learn. A boat that is more stable and less jerky from changes to the helm is a more solid platform for building confidence, or at least I found that to be the case.

It is also worth mentioning that once you own a sailboat, you will be amazed how many experienced sailors are there to answer your questions, show you the ropes, and share in developing your own skills and experience. Giving back to newer sailors is one of the hidden joys we get to provide when we are experienced, have been there ourselves, and now have our own sea stories to tell.

(Below: The Tartan Yachts 365 is a performance cruiser that is provides an exhilirating experience on the water.)

tartan yachts 365 sailboat



What is Your Dream?

To make the transition from casual interest to an experienced owner/cruiser is quite a journey if that is the route you choose. Many don’t aim this high, and are very comfortable with the seasonal enjoyment of sailing by the cabin or seaside summer house with an cute little sailboat sitting quietly on a nearby mooring.

Others, especially those dreamers who fall in love with the adventures on YouTube, may find themselves in 40-foot sailing catamarans, on a fast track to self sufficiency that is both inspiring and doable. These people may likely meet their inspiring couples one day in paradise. Sailing is a small world, and stranger things have happened. I suspect most of the couples with sailing channels are thrilled to meet them as well. Nothing is more validating than to see others follow in one’s footsteps.

As I write this, South African Kirsten Neuschäfer just won the singlehanded sailboat race around the world, completing the trip in 235 days. She is the first woman to win this race in a field of competitors where fewer sailors have completed this solo trip than men and women have been sent into space. It is a remarkable accomplishment.

Kirsten began sailing at an early age, with her parents fully supporting her and her siblings to develop their sailing skills. Now an adult, it is fair to say she is at the top of her game.

For the rest of us, taking the first step to get into sailing is as easy today as it has ever been. And there is no time like now to begin what may become your passion for life.


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