Sailing (Or- Being wet, cold, sore and sick doesn’t seem like a Jimmy Buffett song.)


Sailing in “Hawaiian snow”


In the first part of this tome I advocated for giving a thought towards rock climbing as a possible sport for those seeking an individual freedom recreational activity.  But some of you may live too far from climbable areas and others may go, “Wait, what did you say about bodies and granite blocks?”  For you, I propose another sport with much to offer from an individual freedom aspect- sailing.

The popular thoughts about sailing bring up images of Judge Smails from “Caddyshack,” Ron Rico from “Captain Ron,” or billionaire sailors burning $1000 bills for lighting cigars while watching the America’s Cup.   The truth about sailing is vastly different.  Young people, old people, rich and poor people can all access the water, enjoy themselves and experience individual freedom while sailing.

The quotable CPT Ron…


and an appropriate boat name for this spot.


What is sailing and why is it better than just messing around in a boat? (Or- Isn’t a sailboat on the water just like a Prius or a bicycle on the Interstate?)

Sailing encompasses huge areas of activity and the sailors who enjoy their sport widely consider other sailors to be misguided, crazy or boring.  If you are interested in sailing you are quickly confronted with questions like: monohulls, multi-hulls, one design racing, day sailing, cruising, racing inshore or offshore, just getting out on the water, and a mix of some or all of the above.

You can participate in any or all forms of sailing once you learn the basics on how to more or less safely balance the interactions of two fluids while manipulating a vertically mounted airfoil.  Once you have made headway on that you can then follow activities according to your interests, sailing areas, available cash and potential partners.

I initially learned to sail while in grade school on a golf course pond in southern AZ.  I didn’t think much about sailing again until I was living in the German Alps with a young family and lots of lakes nearby.  I needed a weekend outdoors activity I could do with my youngun’s while their mother was at work.  Bingo!  We could go sailing.   The challenges and joys were real and it was an activity that they liked as well.

But back to the question at hand.  Why an ancient method of propulsion like a sail when you can speed around with huge engines and modern speed? Short answer: freedom and relative costs.

The pointy end is in the front and the stick goes up.  (Or- As Captain Ron said, “Well swab, once you do that job well, you can get a better job, then another and you may become a mate.”)

Most people learn to sail either by starting on a small and simple boat or by crewing on a bit larger boat and picking up skills.  I think a combination of the two is probably the optimum way, if the option is available.  In a small boat you can learn how to manipulate your sails to achieve a desired result while keeping the costs of error very low and easy to recover from.  My first boat was an open hull with a basic lanteen rig (one triangular sail mounted partway back from a corner).

Dbl Eagle’s first yacht


I could sail in small bodies of water near home at speeds that didn’t freak out young kids and if the boat went on its side it was easy to recover from.  That was good since one absolute fact is that if you sail a small boat you will go into the water sometimes.  All these things were great since I had to judge weather, water and could work my way to my goals.

Many local groups use smaller boats to keep expenses low, and open up sailing instruction to kids as young as seven or eight.  If you get a youngster deciding on a course and learning how to get there and back you breed an independent spirit within them.  As their confidence and skills grow so is their ability to direct their exploration.

But don’t sell small boats out.  Pretty well all great modern sailors learned on small boats and the Olympics feature only 1-2 person boats.  Your basic Laser class sailboat is found everywhere from local resorts and community sailing classes to the Olympics.  A well-tuned and well sailed Laser goes like a bat out of hell and is great challenge.

Laser with beginners in light air.


Laser with US Olympian Anna Tunnclife in more air.


Sailing with a more experienced crew is another great way to learn.  I didn’t have this opportunity when I was first learning how to sail since there wasn’t a well-developed sailing community where I lived.  That meant I had to learn AND FAST how to make decisions to protect my crew (aka family) but it also left holes in my knowledge.

After I moved to Hawaii I first joined sailing with others on their boats and I have learned an amazing amount from some incredibly experienced sailors.  I had to take the initiative to introduce myself to a skipper and convince them to take a chance on me.  Luckily, that wasn’t too hard, but to get an invitation to return for another sail I had to show that I was open to instruction and was a good team member.  As I did that I gained more responsibility and then that opened more responsibility.

There is no government process that says who must let you sail, what responsibilities you get and when you must be promoted.  It is up to you and your crew.  If you aren’t happy you can freely depart and find a new crew that may better agree with you.


Fast is relative. (Or- Jeebus! We are going 18 knots and it feels like we are flying.)

Sailboats range the gamut from older boats with traditional sail plans to the new planning boats that actually are above the water and any sailboat can move faster than the apparent wind propelling them.   On a smaller boat that I race we are ecstatic if we can hit and hold 6 knots, on other boats we are feeling down if we dip below 15 knots for any length of time.

Yeah, a power boat can speed right up with enough engine and a proper sea state, but to get to near a sailboat’s theoretical speed is exciting in and of itself.  Another plus is the wind is free. When I was sailing in Southern California in the 1990s there was a midsized powerboat a few places over.  One time talking with the owner he mentioned how he was happy with the dip in gas prices because he could go to and from the Cali coast to a nearish Channel Island for only $100 in fuel.  I was gobsmacked and asked if he was going at hull speed and he said no, that was a cruising speed.  With my sailboat it cost me a few cents of gas to get out and under sail and a few cents more when having the engine on while anchoring and getting into the slip at the end.  My trip to and from the islands was less than a Quarter.  He got to the island quicker, but it cost me less money for the initial investment, in maintenance costs, in fuel costs and as a bonus no damage to my hearing from engine noise.


Entropy is supreme at sea. (Or- Why fix it right when we can fix it right now?)

Boats break, things on boats break, things that hear the word “boat” break and they all need to be fixed.  Sailors get to be handy at making repairs because things don’t like to break when it’s convenient or when a professional is nearby.  Some very rich sailors with the mega yachts have entire crews to make repairs at sea while the owner catches up on binging a Netflix show using the alternate power systems.  The rest of us learn how to make repairs, figure out a jury rig, think up alternates and determine stockage rates of tools, repair parts, fuel and lubricants.

It doesn’t matter what you sail, be it a small boat like a Laser, a mid-range boat, or a larger boat- ongoing maintenance is key and even then it will not be sufficient.  Every sailor I know with at least a modicum of experience can do some small engine maintenance, rig tuning to keep the mast upright, sail repair, and hundreds of other small tasks.  You need these skills since at some point you’ll be called on to fix something or develop a work around while far away from shore.  Or at worst, you must be able to abandon a boat with all your crew and sufficient supplies to survive while you send out an SOS.

I know a couple of sailors who could make MacGuyver throw up his hands and exclaim, “How did you do that?”  I’ll discuss it more later, but a good mechanic, computer or radio tech can make more than enough to be able to finance an unlimited time cruising.   The above principle applies to medicine as well.  Sailors know they are the first responder for their vessel and those who travel beyond the horizon often have more medical knowledge than that.  People who are able to keep systems running through their own, or small group, knowledge tend to see beyond the trope that government must take care of us.


Your horizons while sailing are virtually unlimited. (Or from Captain Ron again- If something is going to happen, it’s going to happen out there.)

Many sailors decide that they want to venture farther than what can be conveniently sailed when you must get back to your starting point before the day ends.  This doesn’t mean you need a 100 foot long mega yacht.  I started “cruising” with my kids in my first boat with some camping gear and we sailed to a small island in big lake and camped the night.

Many cruising areas feature passages which never involve leaving the sight of land.  Some of these areas can be explored for your entire life and you’ll never run out of new places to see.  But the common feature of almost all cruising areas is that the vessel crew decides on timing, routes, speeds, what to see and what to skip, where to spend the night(s) and what is your luxury and how you want to accommodate it.

Poorly named Desolation Sound, BC.

Passage making is not the government’s responsibility.  Depending on where you go the variables can be easy to very challenging and it is all on the skipper, perhaps with the assistance of the crew.  You are responsible for studying the weather, tides, currents, depths, available daylight, strength of crew, logistics of the boat and any other variables and then you make the call.  The government is not there, it is up to your judgment alone.

It is wise to let others know of your plans- but there is no governmental requirement.  It is judicious to not be too adventurous for your experience- but it is your call.  If you speak with the skipper and go, “No, I don’t think is wise (or fun)” it is up to you to make the call to not go.  But the water and atmosphere can always throw in an unexpected variable and it is up to crew to deal with it.  People who seek out this responsibility tend to be distrustful of the judgment of government “experts.”

The first rule is to stay on the boat.


When I am cruising I like spending the night “on the hook” and am not big on tying up to a dock and dealing with paying and all the hassles of dock life like lights streaming  into cabins and/or lines hitting masts all night.  When we sailed in Puget Sound and the San Juan Islands we rarely spent the night in a marina since there was always a new place to anchor for the night.  Once on the hook I would throw the crab pot out, we might go to shore to go clamming or collect mussels and start enjoying evening cocktails.

Here in Hawaii it is a rare interisland passage where we don’t catch a fresh mahi mahi or tuna to grill in the evening, again while enjoying a cocktail after a dive to check out the local sea life.  Because of the realities of anchoring and having sufficient space for “swinging around the anchor” it is a rare night to have many boats close to each other.  If you want to have others over or dinghy over to another boat that is great.  If you want to ignore the others, that is great too.  I especially like those nights which the anchorage is mine alone.

Anchorages sometimes have limits emplaced to protect features or because local knowledge knows some areas are dangerous if the weather turns.  But most anchorages are totally up to the skill and judgment of the skipper and crew.  It is your job to determine the spot (knowing that it your responsibility to stay away from earlier anchored boats), making sure the anchor is set, how long of line should between the anchor and boat (7 to 1 is pretty standard), that the boat will remain safe if a storm blows in/the tide drops or rises etc.

Then when it is time to leave it is up to you to recover the anchor and make your way safely out of the anchorage to open water.  I have been “trapped” in a small anchorage for almost two days because an unexpected swell closed the entrance to safe passage.  But since provisioning the boat is up to the skipper and crew with no government minimums, we had plenty of food, water and beer, but we did run out of black strap rum.

Sunset in a “crowded” Maui anchorage.


Taking the big jump. (Or- When you see the Southern Cross for the first time You know now why you came this way.)

It doesn’t happen to every sailor, and for others it may only happen once, but many sailors look at a sailboat and go why shouldn’t I just sail to Tahiti? (Or to Hawaii, across the Atlantic, to Iceland, around Cape Horn, to Bermuda, or, or, or, or) Plenty of sailors have crossed oceans on sailboats less than 30 feet and most sailboats crossing oceans are under ~40 feet.

You know how to keep the boat moving forward, you know (and have hopefully practiced) emergency procedures, the boat is well “found” (maintained and equipped), between you and your crew you have knowledge of repairs, plenty of food, drink and appropriate clothing.  So why not, why the HELL NOT, shouldn’t you just let loose the lines and sail over the ever receding horizon?

Many sailors do decide to sail away- some for an occasional passage and others for days, years and even decades at a time.  They take advantage of the freedom of the ocean to become worldwide travelers and view the entire globe as a potential port of call.  Thanks to modern communications and transportation these free spirits can stay in contact with loved ones, and for a lucky few their employers.

I have met people who work editing technical publications, freelance authors, and developing/testing code to keep a regular paycheck coming in.  Others are great with their tools and hands and refill their coffers by performing repairs beyond other sailors’ skills.  Almost without exception none of the people are rich in money and they fully acknowledge the sacrifices in other aspects that they are making to live the life they want.

Some are poor, very poor, in a material sense.  Everything they own is in their 32 foot long kingdom.  A kingdom that is decades old but lovingly maintained.  But I have never met a cruiser that didn’t have lifetimes of experience and a spirit that valued nothing above freedom.

Approaching Oahu while returning from Maui. These crew members are working to keep the boat properly healed over.


The first time I went on an extended passage I was with some experienced people and one other first timer.  A few hours after leaving shore we were far enough out to sea that all you could see was the constantly moving blue water spreading to every horizon; that night’s moonless sky was so full of stars it was hard to make out the constellations and the Andromeda Galaxy (M31) was a clearly distinct smudge in the sky. The sound of the water rushing past a few inches from my head as I tried to sleep and the never ending motion was freedom to me.  To the other first timer……….not so much.  He’s a hard charging inshore and off shore racer who can still be counted on to be there and bust his ass to try and help us win, but he discovered that a day on the boat is enough for him.  He pulled his weight and nobody gave him anything but good natured ribbing for deciding that he would buy a flight home and not return with us.  Like I said at the start of this tome- every sailor has their own way and every way right for them.


Crew rest is important while cruising.


Racing. (Or- Don’t kid yourself. If two boats are sailing the same direction there is a race going in in at least one skipper’s mind.)

At one end of the spectrum of sailboat racing are the round-the-globe races.  These are expensive, grueling tests for a solo sailor or crew and the boat.  At the other end of racing spectrum are two skippers betting on who buys the first round while heading to a location.  (There is much truth to the dictum: sailboats are propelled by the wind but are powered by alcohol.) Wherever your race falls on the spectrum it will probably make you a better sailor.

There is no self-delusion on how well you are getting speed.  Those other boats are keeping you honest about how good your choice of direction is, how well your sails are set, how balanced your rudder is and a hundred other details.

I started racing on a regular basis when I moved to Hawaii and have received a constant tutorial on boat speed, sail shape, balancing a vessel, and anticipating wind shifts.  One to two nights a week year round and several weekend days each month I am out there learning.  Plus when we do well, the prize pitchers of Cuba Libres or Margaritas taste extra good.  Since people who make decisions well outside the norms of the fleet can end up winning, most sailors don’t believe in blindly accepting the approved wisdom delivered from on high- they’ll make their own decisions thank you very much.

Start of a race. Balancing boldness and caution is supreme.


Downsides to sailing and cruising. (Or-Guerrilla. Gorilla.  Huuuge difference.)

Well to be frank- you will get seasick at some point.  Everybody does, so the only thing to remember is concentrate on the horizon if you can and go ahead and puke over the leeward (downwind) side of the boat because you’ll feel better after you chum the water.  You will be late at some point for some event important to your spouse/employer because the winds will be either too low or too high.  Sailing is much more work than most people think so you’ll get sore muscles, bruises and “boat bites”; but these are a sign of a life well led.  There is much truth to the saying that the two happiest days of boat ownership are the day you buy it and the day you sell it.

The final downside I’ll address is the US Coast Guard.  “Coasties” do sometimes perform amazing acts of seamanship or flying to rescue professional seamen or recreational sailors. For that I doff my hat at their skill and bravery.  However, the USCG does not like recreational sailors or boaters because: A) We are too independent on the water and have beat back their every attempt to try and force people to use tracking beacons on their vessels; B) We do not like inspections at sea and regard “safety inspections” (aka snooping for drugs or contraband) of our vessels with at best ill hid contempt. Yep the government is the biggest downside to sailing- imagine that.


Lasers during World Championships demonstrate the downside of failing to properly balance the interactions of two bodies of fluids.


When is enough enough? (Or-Swallowing the anchor)

Sailing can be a lifelong experience.  Multiple times a year I see the local yacht clubs running classes for 7-8 year old boys and girls.  I love watching them getting that first taste of responsibility and freedom.  There are young teens I race against who know how to get speed almost like magic in any wind condition or sea state and understand the Racing Rules like a Supreme Court justice knows the law.  I have met older men who were still racing, and beating our collective asses, at 92 years of age.

I shared an interisland passage with a couple in their 70s who had full professional lives, grown kids and multiple grandkids.  After they retired they decided to cruise for 3 years.  They are still cruising and said that their original decision was almost old enough to vote, but one year their 3 year cruise would end.

I hope to have time to cross oceans, see Cape Horn to port under a full moon, gunkhole in deserted bays in Desolation Sound while listening to the sounds of Orcas speaking through my hull as I enjoy a glass of wine and fresh caught Dungeness Crab.  And most of all to continue to enjoy the freedom that sailing offers far from suffocation of government.   My advice is to give sailing a try since it can be experienced all over the Glibertariat.  If a young person is looking for a chance to learn skills, experience the freedom of literally “shaping their own course” and to compete against others- let them learn to sail.  The worst that will happen is that before you know it you’ll read the entire Aubrey/Maturin series of books.

Out for a sail-or- a bad day on the water beats almost any good day on land.


** Except for the Laser photos, I am in or took most of the photos.