What the hell is offshore yacht racing?

Offshore yacht racing.  In the ocean.  Away from EVERYTHING.  Yes.  That fuels me.  In my RestlessUrban intro, I talked about a fateful dinner that motivated me to get on with ‘it’ – whatever ‘it’ was.  When I said ‘yes’, and got out of the way, good things happened.  For me, offshore yacht racing is one of those things.

Why offshore yacht racing became my midlife passion

Welcome to my first series on RestlessUrban  –  my experience as part of a team competing in the 2024 Rolex Sydney to Hobart Yacht Race.

But first, a little background on me, your RestlessUrban Explorer.  Like the bio states, I’m 57, divorced, happily remarried, and a father of one.  I live in the Austin, Texas metro area, but I travel the world for work and for pleasure, looking for adventure and whatever comes my way.  (Musical reference intended.)

How does a land-locked Texan get into offshore yacht racing?  That’s an amazing question and part of my backstory.  Like everything in my life, it was a combination of desire, luck, timing, and opportunity.

From broken arrow to the open sea: how I fell in love with sailing

Making a long story short, and maybe we’ll go back and revisit this particular journey later, here are the high points:  Since I can remember, I was always intrigued by sailing.  It’s probably wrapped up in my obsession with all things that physically move me – bikes, skateboards, cars they all are things that have fascinated and motivated me throughout life.  How fast can you go, how far can you push it, when will it bite back and become catastrophic?  But, growing up in Oklahoma and living as an adult in Texas, sailing just wasn’t an option.  I’m sure we lived near enough to a lake that there was an opportunity to learn to sail – but we didn’t travel in those circles as a family and while I was intrigued by the idea of sailing and the romanticism that comes with it, it wasn’t a thing in Broken Arrow, Oklahoma.

Enter the Jennster.  Jenn, my amazing wife and life partner, did have a sailing background.  Sailing was part of her life.  She is a very good sailor, having grown up with Big’Un, her stepfather who also loves sailing.  They were members of the local yacht club where Jenn spent part of her summers teaching kids to sail and racing dinghies.

Learning to sail in Brazil: the moment everything changed

Jenn and I travel to Brazil for a friend’s wedding, deciding to take an extra week while we are down there for some vacation.  With his help, we pick a seaside resort in Recife.  One of the activities at this resort is taking out tiny, little, single sail catamarans in their protected harbor.  Jenn and I are sitting on the beach watching the day go by and we see these little cats out on the water.  I casually mention (this is almost always the way adventure starts for me), ‘you know, I’d like to learn to sail one day’.  Jenn, who like I said earlier is an amazing life partner, says, ‘why not do it right now, I can teach you’.  We go check out a boat and BAM Jenn teaches me to sail.  I think we sailed on those little cats every day for the rest of the trip when there was even a hint of a breeze.

Here’s something else you need to know about me as we take this Explorer journey together on RestlessUrban — I firmly believe the following to be true and I live my life by these next couple of items.  In life, there are aspirations and there are priorities.  Aspirations are all the things we see and talk about that we would like to do ‘someday’.  And while aspirations can be the start of something, for most people, they’re just daydreams that don’t lead anywhere.  I do not love aspirations.  I love the other thing – priorities.  Aspirations are mainly the things we like to talk shit about with our family and friends and complete strangers to pass the time, being firmly rooted in the concept of ‘what if’.  Priorities are the things that we make happen and provide the fuel that is life.  The main difference between an aspiration and a priority for me is very much grounded in both my professional life and private life.  By the way, I don’t really have a hard barrier between those two ‘lives’, I have always had the good fortune to be passionate about my work and life and I blend the two together as often as possible.  (Definitely more on that as we Explorerer together.)  Priorities, whether they are in a business setting, or a personal setting, share three things – budget, resources and a timeline.  For me, the priority becomes the goal.

Needless to say, I was hooked on sailing and sailing moved out of the aspiration column and into the priority column.  So, I did what I always do with a newly minted priority, I started obsessing on it, I spent time getting educated on it, and I put the three things to it – budget (my money), resources (me and anyone that would help educate me on it), and timeline (right then).

Making sailing a priority: obsession, education, and action

If I’m going to do something, I do it.  Full on.  No half measures.  Sailing was now on the list of ‘learn it and get good at it’.  Around this time, I was working for a guy who is an amazing sailor, a crazy Kiwi named Andy.  Andy is also one of the most creative people I’ve ever encountered and like most hyper creatives, he’s also obsessive and crazy – which is why I love the guy.

Taking the next step: how I got into offshore yacht racing

Hold fast — sailing-ish movie reference intended — we are headed for how I got into offshore yacht racing.  I tell Andy about my Brazil epiphany and ask him how I can get better, fast.  Being a fellow nut job obsessive, he, of course, has a point of view and ‘knows a guy’.  Andy tells me ‘go take some sailing courses with my guy out in San Francisco and start racing’.  This is the critical part and the, at the time, unrecognized spark that would get me into offshore yacht racing.  ‘Racing’, Andy said, ‘will make you better faster.  You have to do things quickly and with precision to race and it’s also fun as hell.’  Sold.  I started, like everyone in the sailing world ‘can racing’ in the evenings after class.  Inshore racing around multiple points.  For fun and the challenge of competing.

What’s the difference between offshore and inshore yacht racing?

Now, most people that race and most people that don’t race but hear about racing sailboats think about inshore racing when they even think about sailboat racing at all.  Inshore racing is exactly what Andy said, fun and fast.

Our more astute readers will at this point be thinking ‘He has been referring to racing sailboats and yacht racing, is there a difference?’  There is a difference between a sailboat and a yacht and there is a difference between sailboat racing and yacht racing and there is a BIG difference between inshore racing and offshore racing.  Let’s go there now.

Sailboats vs. yachts: what qualifies as a racing yacht?

What is the difference between a yacht that sails and a sailboat?  Primarily, size.  While there is no hard definition, let’s set the line at 25 feet.  Below 25 feet, it’s a sailboat.  It probably has very little cabin space and minimal amenities for overnighting on the boat.  Above 25 feet, you start to get a bigger cabin with more amenities that affords you the ability to do more.  These are not hard and fast rules, you will find boats and boat makers that create clear exceptions to these rules, but they are decent guidelines for our purposes.

Again, not a hard and fast ‘rule’, but here goes – sailboats inshore race and yachts inshore race, but sailboats don’t offshore race.  You need a bigger boat with more capability to offshore race.  There are absolutely exceptions to this – single handed and double handed offshore racing is sometimes in smaller boats, but they are very purpose-built boats so they are an exception – more on that in this series.

The unique challenges of offshore yacht racing

Offshore racing versus inshore racing.  This is much more straightforward. Most people that race sailboats, race sailboats inshore, which roughly means near to the shore.  Inshore racing can be sailboats or yachts, several races in a day or an evening, or longer races around a larger course, but still near a shore.

Offshore racing is what the name implies,  offshore, away from land.  One primary difference here is offshore racing is generally far enough from land that a helicopter can’t come save you.  You are on your own.  That’s part of the appeal and the perceived challenge.  It is you, your boat, your team and the elements.  Part of why inshore racing is so much more popular is you can call it off if the weather turns sour.  You can get rescued either by a safety boat or helicopter, or if need be, you can just quit and motor in quickly.

Why offshore yacht racing pushes you to the edge

Not so with offshore yacht racing.  The appeal of offshore racing is what a friend and I talk about all the time – being able to knuckle down with your teammates and ‘EMBRACE THE SUCK’ – endure through the hard stuff.  Persevere.  If you get into the suck, you deal with the suck.  It’s the added challenge of offshore yacht racing.  You prepare your boat, your crew, your plan and it all can end up in the suck for a million reasons.  Your plan can be perfect on paper or in the modeling on your computer, but it all goes sideways for whatever reason.  The weather can go catastrophic – massive waves and storm force winds.  Or, the weather can go the exact other way with no wind whatsoever and flat seas.  That mean you float on it in your fancy racing yacht like a dime store fishing bobber.  The equipment can fail.  Because you broke it, the weather broke it or more often than not, a combination of things broke it.

The role of fear and danger in offshore racing

Two final elements to insert into racing in general and yacht racing for sure – fear and danger.

Fear is often referred to as ‘the great equalizer’ – on one side it’s what stops you from doing something.  That can be a positive thing or a negative thing.  If you let fear overtake you, you might avoid potentially negative consequences, but you also might miss out on the good stuff because you never let yourself out of the starting gates of life.  Fear can also be the motivator that propels you to greater things – fear of failure, fear of losing, fear of bodily harm up to and including death – when you encounter fear and overcome it – life changing things can and do happen.  It’s not for everyone, I don’t foist my beliefs or tolerance for fear on anyone – that is a personal journey that only you can set the parameters on.  But one of the key things we will return to time and time again is overcoming fear, using fear to our advantage and squeezing every bit of life we can get our hands on together in this journey on RestlessUrban.

Any large body of water has an element of danger.  Taking to that water and deciding to race other people and other boats introduces a further element of danger into the proceedings.  Inshore racing is dangerous because you are pitting yourself, your team and your equipment against the elements and other teams of people, their equipment and their skill level – sometimes in very close quarters.  Boats and personal safety equipment are built to a standard that makes this possible and lowers your chances of danger.  But, those chances are never zero.  You are generally closer to help.  If the weather is going to be awful and dangerous, you can just call it off and not go out or go back in before it gets bad.  That’s why most racing is inshore racing.  It’s easier to do, takes less time and is less dangerous than offshore racing.

Offshore racing takes the elements of weather and proximity and man and machine and amps everything up.  It amps up the potential challenge and reward of embracing the suck, but it also amps up the level of risk associated with the activity.  Modern boat design, weather prediction, communications equipment and personal safety gear all comes together to make it less dangerous than it has ever been since the first two boat owners decided to race from point A to point B across a large, open body of water.  But, it isn’t zero.  So, why do it?  We will certainly cover that in this series – my reasons, but my teammates reasons as well.

What’s next: racing in the 2024 rolex Sydney to Hobart

Come with me.  Next up – What is the Rolex Sydney to Hobart Yacht Race and what was my experience.