“So you’re thinking of learning to sail…”

…and you’re probably wondering if this is for you, and who can learn to sail.  And what you can expect to be able to do afterward.  All that good stuff.

Any reasonably coordinated adult can learn to sail.  It’s that simple.  You don’t have to be an athlete.  You don’t need the balance of a gymnast.  You don’t need an advanced degree in math or physics.  (It’s perfectly okay if you suck at them.)

All you really need is a desire to learn.  We’ll do the rest.

“But what’s sailing like?  I’ve never done it.  I have no idea what to expect.”

Well, I’ve been there, albeit with another sport – snowboarding.  I tried that later in life after not skiing since I was a little boy.  I soon became an instructor.  Those experiences inspired me to write this page for you.  And I have a story for you about that further down that puts it all into perspective, but first things first…

Sailing is a very multi-faceted activity and sport.  There are so many ways you can play.  The main thing to know is that it’s very safe.  Are there risks?  Sure.  But most of the risk is reserved for more extreme elements of the sport – certain kinds of racing, ocean passages, etc.  When sailing near shore, and not taking senseless chances, most risk is mitigated and it’s an amazingly safe activity.

So, what’s sailing like?

Instead of me talking about it, why not look at a couple of video clips on our YouTube Channel.  Watch our students in action.  See what you will be doing in our 3-day learn to sail course (or, for that matter, and lots of details aside, any similarly situated learn-to-sail course).

See some clips

There are lots of kinds of sailboats and ways to play on them.  There are small sailing dinghies – little bathtubs 8-10 feet long that small kids start on, and flat, tricked out, teen-length speed racing platforms for kids of all ages (including seniors who are young at heart) .  Dinghies flip over all the time, and that can be part of the fun!

There are keelboats.  These don’t flip over in normal use.  They have heavy fins on the bottom called,.. you guessed it… keels.  These range from small ‘day sailors’ that have bench seats and no real inside to speak of to large, liveable, floating apartments (houses, in fact, compared to some smaller NYC hovels).  These can be comfortably cruised on or even lived on.  How big are we talking?  You’ll learn to sail on something 20-24 feet typically, and when you’re ready for your first cruise in the Caribbean, you will likely be aboard something 35 to 45 feet long.  These will have several individual cabins, with large beds (berths), some windows, fans, and a little storage for whatever you flew down with.  On these cruisers, you can explore a coast or chain of islands for a week or two and be perfectly content.  People usually sail to a new destination each day in a leisurely fashion, allowing plenty of time to explore once ashore.

There are multihulls, usually catamarans, which are basically two very narrow boats spaced apart with connecting bars or what have you.  They can be small ‘beach cats’ with what are basically trampolines in between – wet, wild, and fun.  Ever heard of  Hobie Cat?  Hobie Alter was the man.  Then, there are cruising cats.  These are much more substantial, and can’t really be sailed up onto a beach and pushed off again.  The bodies are not as wide as on a single-bodied cruiser, but there’s less stuff to put in each one, so they’re actually roomier, and more private.  Four corners; four cabins.  The main congregating area is up in a main salon in between the bodies, and the kitchen is there too.  Can party hardy there and not wake up those who went to sleep.  They don’t sail as well as a single-bodied boat, but who cares?  They’re often a little faster and quite versatile.  Catamarans don’t lean to the side easily, because each hull resists leaning to its side due to buoyancy.  But, when the forces get strong enough for one hull to lift up, look out- if you don’t get it back down fast, you can flip over – and once a cruising cat flips over, it stays over.  Beach cats are hard to right (flip back up), but it’s doable without assistance.  Cruising cats actually have escape hatches on the bottom of the hulls in case you’re offshore in bad weather and actually do flip one.  Not usually much of a concern kickin it in the Carib.

All the boats described here can be raced, from round-the-buoys kids’ dinghies on up to round-the-world monohulls and America’s Cup cats.  Racing entails more risk of getting hit with equipment, or getting knocked or falling overboard, but even then, most of these incidents end relatively well.  But, the longer the distance of the race, especially when doing it at night, the more risk is entailed, and there are occasional fatalities.  But given the amount of people who race, and the frequency, the number of serious injuries and fatalities is really quite low.  (In my humble opinion, most fatalities are due to poor judgment by the participants rather than the inherent risk.)

“So, how does this apply to me?  What will my first sailing experiences be like when learning?”

If you didn’t look at those video clips, here’s what to expect.

You’ll learn to walk around the boat safely.  It’s a lot like riding a bus or train.  One hand for you, one hand to grab something when needed.

You’ll sit a bit as you steer the boat with a long stick called a tiller.  Push one way, pull the other.  A lot like rowing gently with one hand, but without all the effort.

You’ll sit a bit as you trim the sails, or pull in/ease out to set them correctly to the boat and the wind.  That’s a little more work than steering, but don’t worry.  You can do it.  (Yes, I know we don’t know you.)

You’ll cross the cockpit from one bench seat to the other as we cross the wind or rotate tasks and positions in the boat.  If you can stand up and sit down, sometimes in a slight crouching stance, you’re good to go.

You’ll go forward to the front of the boat to grab the mooring stick to secure the boat, or let it go when getting underway.  Back to bus & train riding.

What else to expect…

Do not expect to wind up in the water.  You won’t.  You should know how to swim, but we even have students who can’t.  All students wear life jackets (PFD’s) at all times while aboard.  Can’t swim?  Yours goes on before you even get to the pier.  (Don’t get alarmed; the boats don’t flip over; you’re not going in the water.

Expect the boat to lean to the side, or heel, in response to the wind.  This is natural.  You’ll learn how much to accept and what to do when there’s more heeling than needed.  The boat won’t flip over.  It might feel like it to you the first time it happens, but it won’t.  After a little time, your mind and body will both accept this.  By the end of the third day, you might catch yourself trying to flip the boat over to prove us wrong.  Bring it!

Think you can handle all that?

(We knew you could.)  Then look at our Start Sailing page (learn to sail/Basic Keelboat, ASA 101) for more info on the course and how to sign up!

Not convinced?  Told you to check out some clips!  Here they are.

Questions?  Just ask.


Allow me to share a story that helps put it in perspective for you…

I skied as a little boy.  I remember almost nothing of it – I have a few snapshot images in my head, and one sound bite.  Also, one ‘video.’  That was a lesson that ended up with me bailing out of a kids group because I didn’t like the way the trail looked.  One kid after another went down and around the bend, but I took one look and decided there was no way I was going.  It looked wrong.  (For those who ski/ride, it was just a double fall line, but it looked impossibly dangerous to me.  Trail is going left, but sloping right?  Nothing to bank off of?  Not happening…)

Anywho, after becoming so resistant to misguided attempts to get me to go, and basically caterwauling, they finally sent me with a less advanced group.  I remember following the others through an easy glade, sniveling to myself, “this is EASY.”

Soon after that, my parents sold their ski house at Hunter Mountain and we took only one more trip.  Skiing just sort of stopped.  From time to time as a younger adult, I’d consider trying again, but after well publicized stories of celebrity skiing deaths (Sonny Bono; one of the Kennedy’s), and meeting people who’d been hurt skiing or knew others who had been, I was always fearful.  I chose not to go.

I eventually decided to try, and chose snowboarding.  I had a hard time with it, but had my moments.   I loved it and stuck with it, to the point that after one full season (and two lessons at the end of the previous one), I applied to become an instructor.

I was no pro snowboarder, nor an amazingly talented prodigy.  I felt I’d come a long way in a short time, but wanted to teach as much to ramp up my own progression as anything else.  One of my main motivations was to prove my hypothesis that I could teach others to snowboard better than I’d been taught.

So, I chose one of the more inviting mountains, whose philosophy was along the lines of… “You don’t have to be the best skier or snowboarder on the mountain to teach.  You have to be good with people.”  I started filling out their application on line, being very modest in how I represented myself.  (Intermediate, mostly blue terrain, no park, etc.)  About half way through, I got a phone call from a former client who said he took our course about three years ago.  He had bought a boat, and was thinking about keeping it at City Island (where the Sailing Center is located).  We chatted about the boat and his options for storing it for awhile, and eventually, I realized I didn’t know who I was talking to.  So, I asked, and he told me his name.

I remembered him.  He and his adult son were snowboard instructors!  I distinctly remembered them, because after they finished the course, they were so happy with it that they offered for me to come try snowboarding any time.  And at the time, I was like, no f-ing WAY I’m doing that.  I saw it as some daredevelish thing that wasn’t for adults, and wondered why they were doing it.  Of course, I had never done it nor seen it live so what did I know.

So, I said to the client, Robert, “You’ll never guess what you caught me in the middle of when you called.”  “What?” “I’m filling out the application on line to teach snowboarding at Okemo!”

“They’ll hire you in a hearbeat.”

“? But, but…”

And I gave him every reason why I thought they shoudn’t/wouldn’t hire me.  And he had an answer to every one.  And, he was right.

If I could learn to snowboard at the age I did, and be able to teach after basically one full season, then just about anyone can learn to sail.  Straight up.  When I flat out refused to try when invited, part of that was because I had misconceptions about what was involved, and what you could do in snowboarding.  It’s not all about inverted aerials in the halfpipe, or dropping off cliffs, or doing death defying stunts sliding off rails or through trees.  It’s also about mellow cruising down basic trails, gliding along slowly and in control, with little risk to yourself or anyone else.  The reason I tried it in the first place was that friends who were aware of my potential interest advised that I didn’t have to ever be out of control and go fast enough to get hurt.  I could take a lesson, stay on the bunny (beginner) slopes or greens, and just choose to stay in control at all times.  And they were right.  So I tried it, fell in love, and have not looked back.  Of couse, now I dabble in most of the daredevil stuff, but I choose it carefully.  Halfpipe? Love it, but if I ever get good enough to reach the top, I’ll stop before I leave the pipe and risk landing on the edge.  Park?  I’ll do a straight glide over easy boxes and that’s it.  Jumps?  The smallest they have.  Moguls and trees?  I struggle with those but scope it out before I go, and only when I’m feeling fresh enough and have the right mindset to relax and not get stiff.  Cliffs?  Probably not for me…


You want to know what’s involved in learning, and then doing it on your own afterward.  You want to know the risks, and how to mitigate them.  You just want to know what to expect.  So there it was.

Questions?  Just ask.

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