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Go Back   SailNet Community > Contributing Authors > Learning to Sail Articles
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Old 08-31-2001
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Mark Matthews is on a distinguished road
How Other Sailors Learned


Every journey begins with a single step. Faltering here and there in the beginning is just a natural part of the learning curve.
Every sailor has a story about how he or she got interested in the sport and began to understand the forces at play. For me, it was at Henderson Harbor Yacht Club on Lake Ontario that it all began. I had never seen a sailboat "pop-a-wheelie" before, but sure enough, my brother managed to ram the sailing school's 14-foot Bantam into, and right up onto the dock, where it hung with its bow pointing skyward at a crazy angle, sails still straining in the broad-reach position. The boat rocked lightly back and forth tilted to port as its dazed crew spilled out onto the dock. A crowd of concerned parents, captivated students, and the sole sailing instructor clustered to assess any personal injury, looking past the chips and splinters of fiberglass that had formerly been the bow of the boat. Luckily the crew was intact, but the physics behind the collision left the first of many impressions to follow. When translated into momentum, the wind made nothing impossible. The sails came down, the crew lumbered out, and the unscheduled fiberglass repair class got under way. Yeah, I was that passenger.

Tom Wood    [SailNet Contributor] Like many sailors, I was out on the water under sail at an early age. Summers on the Minnesota lakes being short, the exposure we kids wanted most was not classroom study or intense competition, but rather lazy afternoons drifting aimlessly and getting sunburns that would frighten the most jaded dermatologist. The friends teaching me to sail knew only how to go downwind, but the lake was small enough to wade home along the shore, towing the boat by its painter. I have always remembered those golden summer days with great affection and a faint reddening of the skin.

Years later, I bought a 14-foot plywood racing dinghy with a spongy centerboard trunk. Armed with basic knowledge from a few beginner's books, I launched my dream ship upon the Great Lakes only to find that a great deal of stamina was required to sail, learn to sail, and bail at the same time. Since that day, I have had the good fortune to own 12 more dream ships, and to sail on hundreds of OPB (Other People's Boats).

Sailing has taken me to ports of the world which were totally unknown to a young Minnesota lad. It's been a lifetime of learning, stretching my capabilities, and learning about distant lands and other people. Yet, after all these years, some of my fondest memories are of lazing around an ice cold lake in the early spring and bailing like the devil while trying not to capsize.


One of the advantages of learning on a small boats is that it limits the amount of damage you can do in the likely event of a collision with another boat or a dock.
Bruce Caldwell    [SailNet Contributor] After a series of basic keelboat lessons, the day came to be tested. First I had to get away from the mooring. I released the mooring line from the bow of the Catalina sloop and raced back to the cockpit to power away from the expensive yachts tied up nearby. Although I was twisting the outboard's throttle, we weren't moving forward. Instead, we were drifting closer to a beautiful green hull of a boat at a nearby mooring. The instructor pointed out that I should shift out of neutral. I did that and looked forward to get my bearing with hope. By then, however, the instructor was shouldering me aside so that he could push away from the green hull, against which we had drifted after the propeller snagged our dinghy painter. The instructor re-tied the painter, much shorter now, to the mooring, and I managed to get the boat into the bay and shakily take it through its paces. Afterward, the instructor offered to test me again later, much later, at no charge, after I had put in more sailing time, preferably in a dinghy.

Poky, the dinghy I bought and christened for its most notable characteristic, taught me to sail over many hours alone on the bays. Take the test again? Thanks, but no thanks. The instructor has gained a following at the local comedy clubs, and I don't think he needs any more material from me.

Randy Harman  [SailNet contributor]   I didn't see an ocean until I was 20, in the San Francisco Bay area. I got seasick before the boat left the dock. After moving to southern California, a friend told me to try sailing: the different motion; the peaceful quiet of going through the water without an engine—all were supposed to help one prone to seasickness. (He was right! I've never fed the fish from a sailboat!)

For a full 12 months, I read every book I could get my hands on about sailing. (Royce's sailing illustrated got me started.) The first day I boarded a sailboat was the day I bought a 17-foot daysailer, a German made Pirate Cadet class. The next day I singlehanded it and the next weekend I took it out into the ocean. I was hooked! That beautiful centerboard sloop was all brightwork & bronze with a wishbone tiller. She was very forgiving but also responsive to quickly let me know when I wasn't doing things properly.

Since that time, I've raced/sailed on many vessels while owning only four—so far.

Bill Betts [SailNet user]    I don't know why no one in my family or acquaintance had any boat much less a sailboat, but for some reason when I was 18 I decided I needed one. I bought an eight-foot, foam-wrapped-in-plastic boat with an aluminum mast. A Snark maybe? The day I brought it home strapped to the top of my car, my girlfriend (brave girl) and I sailed it straight into Altus Reservoir. As I write this 30 years later, I don't think we even had life vests. We sailed 30 minutes straight out Then the clouds came up, the wind picked up, the lake picked up and it took us about two hours to sail it back against the wind. Well after dark, we got it to a place we could beach it and walk to the car. At one point, while we were being blown into a tree that was growing over the water, I looked down and saw I was sitting to my waist in water! God bless Styrofoam boats and the fools who sail them.

Today I have a 40-fot Beneteau and dream of sailing around the world. I still make my share of bonehead moves. What's that about the difference between men and boys? The price of the toys?

John Hudson    [SailNet User] When I was in about 4th grade, I "read" a picture book called Dove, the story of a young man soloing around the world. I was captivated at a young age. I must have forgotten about it, then in high school I stumbled across the actual novel of young Robins exploits and read and reread it. That's where the dream started.

Gary Leyritz    [SailNet User] When I realized that I "had" to learn to sail, my wife and I signed up for a sailing class. I had already gone out on several boats, but still didn't know why the boat healed quite soooo much, or exactly what made it go in the direction that I wanted to go. My wife went to class with me, (probably to more to get out of the house than anything else). Still, we did so well that before the class was even over, I made an offer to buy a sailboat.

Our first lesson came from first hand experience, and can be summed up in the following: always make sure that the outboard motor has enough gas in it. As we motored from the dealer to the moorage, about two miles, we got about half way when the motor sputtered and stopped. I opened the gas cap on top of the engine and cussed a little. A 5 to 10-knot wind blew us toward the shore until the centerboard hit the bottom, putting us about 100 feet from shore. I discovered that we needed a wrench to loosen the bolt holding down the swing keel. And we didn't bring along a tool box.

Since it was the middle of February and there weren’t many boaters out that day, I decided to raise the mainsail in the hopes of leaning over enough for us to sail off the bottom. All this did was to bring us closer to shore. After lowering the sail, I spotted a speedboat across the lake and was able to get his attention by tying a life jacket to the paddle and waving it. The boater arrived shortly, supplied the much-needed wrench, and towed a rather embarrassed wannabe sailor to the marina and my newly acquired slip.

That was almost 30 years and several boats ago. We have run aground several times since that first day, but came prepared for such events and were able to continue our cruises. Every time we leave the dock, we learn something new about ourselves and about sailing.

Randy Murrah    [SailNet User] I grew up at Lake Texarkana (now Wright Patman Resevoir) near Texarkana, TX. My father had a 23-foot cabin cruiser that we spent nearly every weekend on. My perspective was that powerboats were the only way to go, and our lake had no sailboats on it anyway. A friend purchased a 18-foot catamaran and at the age of 40, I finally got to go sailing.

I was immediately hooked. The heel of the boat, the pull of the sails, and the hum of the rudders got my blood pumping like nothing else I had ever experienced. It wasn't long until I was a sailboat owner myself and purchased a 30-foot keelboat for my first sailboat. The previous owner told me it was too big to learn on but nevertheless, I bought it. I read everything I could get my hands on about sailing and taught myself how to handle the boat. It’s been a little over a year since I began sailing. I sail my boat mostly single-handed and even when my wife comes along, I am still singlehanding. I can handle my ship very well now and usually sail out of and into my slip. I can see myself living on a boat and plying the oceans someday when I can break free of shoreside obligations. Till then, I'll just enjoy the lake breezes on the Blue Dolphin at Eagle Mountain Lake.

Dan Cowett [SailNet User] No one in my immediate or extended family ever owned a boat that I know of, but I have been fascinated with sailboats and boating since an early age. Without much boating experience except for an occasional power boat trip and an awesome catamaran ride, at age 38 I decided it was time to learn how to sail. I convinced my girl friend to sign up with me and take the weeklong course at a local yacht club.

We learned to sail on a 14-foot Aqua Finn. The first lesson was righting the boat after a knock down. What a unique experience that was! Most of us had never seen an Aqua Finn much less getting pushed out into a deep bay and instructed to stand on the lee rail and pull the mast over until the sail was in the water, and then having to right it. What a blast! After a class race at the end of the week we were so hooked on sailing we could hardly sit still.

A few months later I purchased a 26-foot trailerable sloop. My friends and family thought I was nuts, but the passion needed to be fulfilled. Sailing has been enormously fulfilling.

Since then I have read every piece of literature on sailing that I can get my hands on, taken a Power Squadrons course, and sailed on several lakes on NC and FL as well as sailed some on coastal waters. Bonnie and I love cruising. Gunkholing and sailing to different places seemed like something unobtainable a couple of years ago, but we made it a reality in a short period of time. Now we want a more seaworthy boat so that we can eventually do the "real deal" and get into extended cruising.

I will have to admit that when reading accounts from sailors that were conceived on sailboats and have been sailing since they were five years old, I initially thought that it was too late for me to get involved in the sport. Fortunately I found out that I was dead wrong.

Experience is the teacher and I have a lot to learn. For new sailors like my self and for others thinking about sailing who may read this, all I have to say is...take the chance—go for it—you won't regret it!


While Steve and Linda Dashew's Beowulf is an impressive crusing vessel that has carried the pair thousands of miles, the sailors have ample experience in lowlier vessels and have learned much from the time spent in those.
Famous Sailors    Take heart in these tales taken from the well-trod path of landlubbers who made their way to the water to thrive among the wind and the waves. Here is how some of sailing's more recognized practitioners got started:

Steve and Linda Dashew
In 1975, the Dashews decided to go cruising on their 50-foot ketch Intermezzo. That was followed by more cruising on Intermezzoo II, Sundeer, and Beowulf as the Dashews took to the oceans of the world. Steve Dashew is the author of numerous books on cruising.

"I am not sure when I formally learned to sail. My parents told me I was conceived on their Friendship Sloop and then grew up sailing. By age eight, I was used to conning the family schooner and by 13 my dad would let me take out 60-foot Alden ketch to daysail with friends. My first sailing dink was a jury-rigged rowing dinghy, complete with lug sail. The memory of the freedom of sailing off downwind is still with me. However when the time came to sail back to windward, I learned the first of many lessons about underwater foils. My crude plank would not stay in place and I was forced to accept a tow back to weather—embarrassing, even at age eight.

"Linda learned to sail crewing on our racing catamarans before we were married. We won the Shark (20-foot cat) championship when she had only sailed a few times. However, she was a natural, and on every tack, jibe, or mark rounding, we'd pick up distance on our closes competitors.

"As all our sailing time was spent on the race course, it was cruising that provided the big learning curve. And we learned the hard way, primarily by doing it. When we first left for the tropics (Mexico, then the South Pacific) on our 50-foot Intermezzo our clothes were too heavy, we did not have a single fan and the large deck awning was blue just the right color to attract and radiate heat! The engine ran three hours a day trying to keep the fridge cool, the self-steering system didn't do its job unless seas were clam, and I had yet to tear down and overhaul the head. Books were far and few between—none with any real answers which is what led to our first effort in the field and eventually to our Offshore Cruising Encyclopedia. However, everyone else was in the same pickle, and eventually, by the time we reached New Zealand, we had a pretty good idea of what we needed to do to improve the situation."

Peter and Olaf Harken    The Harken brothers are the founders and directors of Harken Yacht Equipment, Pewuakee, WI. Apart from their renowned industry affiliation, they are avid scow and iceboat sailors.

"Our grandfather owned a fleet of sailing ships," recounts Peter, "so sailing blood was in us. We were raised in the Philippines. Olaf and I learned to sail at the Manila Yacht Club, though we weren't members. At that time you had to earn your way. We found an old Snipe in the dump and together fixed it up. We learned from the school of hard-knocks. The Snipe was our goof-off boat. We once figured the more it heeled, the faster it would go. We also crewed in the active 110 and Dragon fleets, and on a range of offshore-type boats that sailed on the then-beautiful Manila Bay.

 "Later when were both at the University of Wisconsin and had joined the University Sailing Club, the Hoofers, we got into dinghy racing and iceboating. Our parents weren't afraid, and we weren't either. I think that has a lot to do with knowing how to swim. Not being afraid is key to sailing enjoyment."

Peter Isler    A two-time navigator on winning America's Cup boats, and a professional sailor and author, Isler has served as one ESPN's commentators for the America's Cup. He's also a board member of the Amercian Sailing Association, and the author of Sailing for Dummies and At the Helm: Business Lessons for Navigating Rough Waters.

"I was a baseball player and a power boater until I was 13 years old when my family moved from Cincinnati, OH, to Rowayton, CT, on Long Island Sound. Granted I have always loved being on and around the water, but that never would have led me into sailboat racing except that across the street from our new home, as luck would have it, was a family of sailors. The kids were all close to my age and their parents were into sailing big time. The father, Ted Jones, who at the time was an editor of Sailing World magazine, arranged for the local yacht club to bend the rules so that my brother and I (non-members) could attend the summer junior sailing program.

"Even though I was starting about three years later than most of my peers, I loved it from the get-go. Still, my first time out single-handing a Dyer Dhow was far from propitious: I got the boat stuck in irons and the instructor finally came up to me in a Boston Whaler and said cynically, ‘You don't know how to sail, do you?' He was absolutely right and I felt about one-inch tall. But it wasn't long before I knew my leech from my luff and was immersing myself in the Jones family library in the hours when I couldn't be sailing. In the next few years I spent a lot of time crewing aboard Lightnings—a boat I still remember very fondly. It wasn't until just before college that I started doing very much driving."


Cam Lewis has honed his skills in a variety of boats from Finn dinghies, to the 110-foot multihull Team Adventure.
Cam Lewis
    Perhaps no one can claim as much varied success in the sport as Cam Lewis. He's set records in around-the-world competition and dominated the Finn Class. He's won the America's Cup, and sailed in numerous professional arenas, and particpated in just about every level in between. Lewis began as a dinghy sailor, racing Finns, 505s, Lasers, and Flying Dutchman. He has twice won the Finn Gold Cup champion and was twice 5-0-5 World Champion. With Bruno Peyron, Cam was winner of the first Jules Verne Trophy for sailing around the world in a record time. He has gone on to sail the Whitbread and America's Cup and won the Transpac on the multihull Explorer. His 110-foot multihull Team Adventure took third place in The Race. 

"I grew up around boats. In fact, I've been told I was conceived on the sail back from the '56 Bermuda Race on Caper. I started racing as a kid and won my first race at the age of six. We had an O'Day Super Sprit on the pond in Massachusetts where I lived as a youngster. As a kid, I mainly raced on North Haven Dinghies on the waters of Penobscot Bay. By local racing rules, I had to wait till the age of 12 before being able to helm my boat."

Dee Smith    A renowned tactician and all around racer in the grand prix arena, Smith is a former Whitbread competitor who will be participating in the Volvo Ocean Race aboard Amer Sports One alongside Grant Dalton.

"I was about 12 years old the first time my dad and I took out his new Gladiator in some race off Santa Cruz. We were just racing with a main and a jib, sailing along mid-pack when a boat ahead jibed and headed for the beach. My dad instructed me to find the binoculars and start looking for the mark in there, because the guy who jibed had set the marks earlier. Sure enough, the mark was in there—so we jibed over, and won the race on corrected time because almost the whole fleet had followed the lead boat to the wrong mark. It made a real impression on me—there's no reason not to do well on the racecourse, so long as you just keep your eyes open."


Dawn Riley sailed America True to an impressive finish in the Louis Vuitton Cup, but she spent a lot of time in the boat yard and on smaller boats in order to get to that point.
Dawn Riley 
   This former Rolex Yachtswoman of the Year  has a resume that includes crewing on the maxi yacht Morning Glory as the boat set the all time course record in the 1996 Sydney-to-Hobart Race. She was also team captain of America3, the historic all women America's Cup team in 1995, a member of the winning America's Cup team on America3 in 1992, and skipper of Heineken, the all-women team in the 1993-94 Whitbread Round the World Race. In addition, she impressed her America's Cup colleagues and competitors by leading AmericaTrue to a respectable finish in the Louis Vuitton elimination series at the 2000 America's Cup while serving as skipper and CEO.

Growing up in Detroit, MI, where she sailed on Lake St. Clair, Riley says that she became obsessed with sailboat racing at the age of 13. She joined North Star Sail Club and became commodore of the junior sailing program. Riley said it was difficult to break into professional sailing, and she had to clean quite a few boat bottoms and learn to fix outboard motors before people took her seriously. But she didn't give up.

We invite readers to share the  experiences that have resulted from their own pursuit of mastering the elements in learning how to sail. Click here to send us yours.


Suggested Reading:

Sailing Basics by Steve Colgate

Wind Orientation by Mark Matthews

Learn to Sail in a Dinghy by Sue and Larry

Buying Guide: Personal Flotation Devices

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