Building skills with Celeste


Where have 11 months gone since my last update posting?

…I can tell you I have done some tallship sailing on Elissa, a three-masted, iron-hulled sailing ship built in 1877 in Aberdeen, Scotland now in the care of the Galveston Historic Foundation. I’ve also done lots of sailing on my own boat, quite a few refit projects, and her first haul out – but, more about that later.

Since its raining today, lets take a break and continue with step 3 in the 4-part series of the process undertaken to get this sailboat journey underway.

As a refresher, those 4 parts are:

1) Understand your Dream,
2) Limit your Search,
3) Consider your Skills, and
4) Seek Alternative Purchase Options.

Today, I want to address Consider your Skills. Quite frankly, I had nothing more than old fashion rowing boat experience from fishing on a lake, a bit of canoeing and one day on a kayak. Not quite enough to be mildly knowledgeable at the time.

Before purchasing a boat I decided to get some sailing experience. So I jumped an airplane to Vancouver, British Columbia for a weekend of fun and an introductory day-sail on the English Bay with the Marla at We had a good experience on a calm bay and a knowledgeable captain who provided examples and let our little group do all the line-handling. I was hooked. – no turning back!

celeste-4On Celeste a 31′ Dufour, we learned to lower the dinghy from the fore deck and proper attachment to the stern. Marla, our captain and instructor, gave us a briefing of the bay using nautical charts, some dock line-handling skills and we were motoring out of the marina from Granville Island in no time. Check out this short video of the experience.

The day was filled with learning to properly hoist the sails, setting the jib, trimming sails, and being helmsman. At lunchtime we learned to heave-to and enjoy the picturesque bay. Given the wind direction we learned to sail into the wind avoiding “in irons”. Returning, we did some downwind sailing, lowered sail, and motored back into port. Marla docked while we crew handled the lines and performed a proper tie off using the cleat hitch we were taught.

Overall, a good introduction and quite complete addressing many of the topics more fully learned in the ASA 101 Basic Keelboat Sailing – my next port on the journey learning new skills.

The point is, that first day sail was a real confidence builder. But it also highlights the various knowledge areas were deeper skill development would be necessary. Most importantly, it solidified that my dream to circumnavigate was something that could be made a reality.

So why does this story matter?

The bottom line: it is important to know your skills AND you ability to obtain them.  Any boat chosen must work within this limitation.

I purposefully did not lay a plan for a 50′ or greater boat. With my limited skill set, that size boat would be too big. I am avoiding a boat with a mizzen mast. It adds another level of complexity to single-handed sailing. A catamaran sounds great and provides so much more room and quality of living space. But it also comes with a wider, larger boat to handle in small slip spaces where I have very limited experience. After all, docking is like landing an airplane. It is one of the most risky aspects of sailing.

Another day I hope to share my experiences tallship sailing.  This experience taught me line handling, knots, sails and maneuvering, maintenance, and more importantly….the need for discipline in sailing to avoid risks and plan ahead.

Through all this skill building, I made the commitment and located a sailboat to pursue my crazy circumvention dreams. Stay tuned.


Searching…deciding sailboat details?

Last time I shared the four phase process being followed as I get this sailboat journey underway:

1) Understand your dream,
2) Limit your search,
3) Consider your skills, and
4) Seek alternative purchase options.

Today I want to focus on limiting the search to vessels that meet the mission and your budget.

One big lesson learned is to avoid settling for the convenient option – the one that lets you get a sailboat now. It may not meet your true needs. Separating needs from wants is difficult. Take your time to really determine the differences.  A big part of my search included visiting local marina sailboat brokers, attending sailboat shows like the Strictly Sail Miami Boat Show, and watching videos of sailboat tours on YouTube. Honestly, walking around and talking with others at a local marina helped immensely.

Touring these sailboats, I quickly became infatuated in a escalating dream I couldn’t afford. Amel, Hylas Yachts, Hans Christian, Hallberg-Rassy to name a few – their size kept increasing, features over the top, and price tags bewildering. Finally I came to the conclusion that I am not buying a custom home. With each rationalization came the inevitable…how much longer will I need to work to save enough to buy ______? … fill in the blank.

So I stopped looking.

Instead, I went back to the mission realizing that I had stepped outside of it.  A fundamental requirement for me to sailing around the world is that I have a dependable boat that can do that – safely. This is when I stumbled into the discussion about “the perfect blue water cruiser”. Exploring the internet using this search term will provide more than a handful of opinions. Searching resources like Blue Water Boats, SailNet, CruisersForum got me back on track and provided a glimpse into technical details for particular boats with a bit of passion from their owners. But this is when I really started to learn some differences. The ones that would allow me to decide on a boat that will be within my budget.

Slocum Spray
on April 24, 1895, Joshua Slocum rebuilt the 36′ 9″ (11.2 m) gaff rigged sloop oyster boat named Spray and set out on a solo circumnavigation of the earth.

Books about circumnavigation and the features of those sailboats helped immensely too.

The first big take-away is reconfirmation that it does not take a lot of money – but it can, needlessly ! Why? There are so many options and examples of people doing this type of sailing with boats that cost less than a car. Helpful is that many of the boats in my price range are going to be “used” so there are plenty of examples of people doing what I want to do with examples of how that worked out. Happily there is no need to be a rich man for this dream.

The keys I stumbled upon include themes like:

  • Simplicity – ease to operate, repair, and maintain while at dock and underway
  • Solid – construction of the boat and its systems that have proven themselves dependable under many different circumstances
  • Sailing Qualities – wind and wave performance that has a lot to do with the keel, rudder, and type of mast
  • Safety – most things happen slowly on a sailboat at 6 knots of speed or less. And if it broaches or gets knocked down by a wave in extreme weather, they tend to pop right back up or the issue provides ample time to remedy with keen thought (watch Robert Redford in All is Lost)

Probably three of the most fascinating resources that contributed to my understanding of all this new information includes Nike Steigar at WhiteSpotPirates, Dan and Kika at Sailing Uma, and Drake Roberts at The Real Cruising Life.  Each has a YouTube channel as well.

Nike took a neglected 1992 Reinke Super 10 (37’) that cost $8k in Panama investing another $25k to make it bluewater ready – check out her videos at WhiteSpotPirates. Dan and Kika did a similar task taking 1972 Pearson 36’ and fitted her to meet their style which is fully documented at Sailing Uma. Drake has a Westsail 42’ that without any repairs could be in the $50-70k range (see Yachtworld for indicative pricing of boats).

Each of these examples solidified my personal belief to purchase a sailboat I can sail today without a several year process to make her seaworthy. The boat I purchased may not be ready for circumnavigation at the time of purchase, but I will not be dock bound or “on the hard” for several years to get ready.  I am quite comfortable doing smaller projects (will be documented in this blog) as I journey to get ready.  Sailing to build skills and reward myself with time on the water each step is an objective I had from the start. So yes, a bit of immediate gratification tends to keep me motivated.

In the end, deciding on a boat is not so formulaic. Get out there. Investigate. See which ones you like or do not like. But be careful to not focus too much on the “floor plan” and creature comforts. There are technical considerations to take into account as well.

islandpackat-1-740There a few things that I anchored on after much reading and investigation which link back to the 4 S’s above.  These are those “technical considerations” worth investigating:

  1. Keel – 6’ draft without any centerboard. I didn’t want the centerboard to malfunction or lock up which takes away from simplicity. But I did not want a shoal draft (typically in the 4’ to 5’ range) so that I would have more upright stability in rough seas.
  2. Interior Table – In the salon I like the ability to douse sails or just throw things down the companionway to get canvas or lines out of the way and sort them later. This means that having a fold-up table makes a big space to do the sorting. In the boat I ultimately selected, I have about a 5’x12’ working space below when under sail because the table can be folded and stowed.
  3. Length – About 36’ in length provides ample living space with the boat not being too large making it difficult to handle by myself or too small leaving me crowded.
  4. Keel Stepped – The mast stepped on the keel because I just like the stability knowing that the mast has a firm foundation over and beyond an engineer’s calculation (it’s worth checking out “keel-stepped” vs. “deck-stepped” masts).
  5. Sloop Rigging – adding a mizzen mast with another sail just adds too much and makes things more complex – more rigging, more winches, more of more. A mizzen has some interesting sailing qualities and I’d consider a mizzen if I did not have the requirement to be able to single-hand my sailboat – simple and solid is the objective.
  6. Righting from Knockdown – maybe I’m a little bit overcautious. But I want to have documented examples where the sailboat I choose has been knocked down repeatedly and bounced right back up. There might be some water below, but I want to know that if I screw up, the boat will keep me safe.
  7. Self Steering – I believe this to be my #1 risk management tool. I want to know that I can trim sails, make adjustments, gather meals, and rest without being glued to the helm. There are lots of choices here, but my objective is that the chosen solution must work in all types of weather.
  8. Low Winds Efficiency – I want to sail, not motor. When winds are low, I didn’t want a sluggish boat. It must have some of those qualities to slice through the water with minimal drag.
  9. Traveler Setup – outside the cockpit because I don’t want to be tripping over the lines or moving around the blocks to get into the companionway. A poorly located traveler to adjust the mainsail distracts from simplicity.
  10. Decision Making Choices – These are critical for my approach to risk management; including, navigation and radar systems, AIS, EPIRB, Solar/Wind Power with Battery Bank. All of this must have a manual backup approach should I lose power.
  11. Comfort Choices – These are things not so high on the list, but if they can be attained, all the better: water maker, refrigeration, galley with propane burners (no oven), microwave, exterior grill, and HVAC (this is a long shot and very low on the priority list).

So there you have a few of the details for “my perfect boat”. Sounds easy, right?

But there is more… I also learned that since I would be buying a used boat there would definitely be a few projects that would likely be required, no matter the boat selected. These are things I knew that within 5 years of getting a boat, these expenses would likely be required, no matter what boat I purchased. Of course, is a prior owner had already performed these in the last year, they would be priced into the boat placing it outside of my price range…potentially.  These are:

  • Haul out, sand, and paint the bottom
  • Replace standing and running rigging
  • Remove and step the mast
  • New sails
  • Replace through hulls, plumbing, and electrical wiring

My thinking is that I want to know all these systems and components are safe, top notch before I set out on a full circumnavigation. I was not going to trust the work of others done at some indeterminable time in the past. This would also help inform my budget over the next 5 years.

Now the more difficult part …which boats will fit this list?

Sailboat…which one to choose?

Knowing what I know now….I would have purchased my first sailboat at least 31 years ago. I never imagined how many inexpensive options there are obtaining a sailboat capable of circumnavigating the world.

Choosing a sailboat can be an overwhelming decision. But I’m convinced that it does not need to be. Looking back on this experience, a recommendation is to break the decision into a few components; namely,

  1. Understand your dream and the sailboat’s mission
  2. Limit your search to vessels that meet the mission and your budget
  3. Consider your skills and avoid selecting a “project” boat with excessive repair requirements
  4. Seek alternative purchase options to maximize value

In this post, I am going to limit the topic to understanding your dream and the sailboat’s mission.

Do you dream to circumnavigate or hug a coastline?

Might you prefer to be a part time or full time live-aboard?

Will you be single handed sailing, have a companion, or utilize a crew for longer passages?

What are your budget limitations?

You see, how you answer these questions and the myriad of others that will spring into your mind, you will quickly begin to see that there are alternatives in the type of sailboat you may select. To get my mind wrapped around these options, I chose to read books, watch movies and videos, attend a few sailboat shows, do some sailing with others, and consider the contribution of other fellow adventurer blogs. My conclusion is that there is more than one way to reach this conclusion. It is more important to take your time and not rush into purchasing the first sailboat that fits your budget.

In my case, the more I contemplated which sailboat – the lower my budget became. I quickly realized that the cost to get started didn’t need to get larger. Boat envy, or the insatiable desire for something bigger and more luxurious than I actually needed seemed to diminish. Ultimately, I set the objective that the price of the boat did not need to coast more than a typical used, middle class car in the USA.

A few resources to get you started include:

There are many more resources available through an internet search on sailing. The objective is to nourish your dream and to figure out exactly what the mission of your boat that is required.

In my case, I also took a trip to Vancouver to sail on a Dufour 31 for the weekend. It was actually my first real sail learning how to operate a sailboat. This was much different from a 2 hour recreational sail on the schooner America 2.0 from New York City that I did the previous year in Key West, Florida.

So what is my dream and mission for the sailboat?

My dream is that on the first day of my retirement that I will depart my home port on a non-stop circumnavigation – solo. If a 16 year old like Robin Graham or even Zac Sunderland can do it, surely
an old salty dog like me can do it too!

My boat must be able to be sailed single-handed. This requires that it have simple systems. It must be easily repaired while en route. It must not require complex or difficult to obtain spare parts – preferable those that I can carry along on board. It must be comfortable both in the cockpit and bellow deck including ample room to exercise while at sail. The sailboat must have a reasonable galley for food preparation and sufficient storage capacity to It hold significant stores of foodstuffs. The mission will require that this sailboat generate sufficient power to be “off grid” and make freshwater.

That’s a tall order. But one that quite reasonably fits into my limited budget. Next week, I’ll address the search for vessels that meet this criteria of the mission.

Sailing…the ultimate “tiny house”?

Last week I answered my question about what makes me happy with:

Traveling with curiosity and purpose. Learning. Becoming aware. Asking Who? What? Why? When? and How? Deep and meaningful relationships.  And fitting all the abstract pieces together into a wonderful fabric of experience.

Well, after searching I discovered that there are quite a few ways to do this. For example, you could achieve this through:

Each of these has their own pros and cons. The furnished apartment option opens the world to any continent and any city. The RV or tiny house on wheels limited things to single continent, for the most part. Although using my employment as a means is enticing, it means I can only go where the company wants me to go. Flights and hotel living means I could only go on a few trips a year due to the prohibited costs.   Furnished apartments was intriguing so I could “go deep”, but it was like having two homes at one – the permanent home and the temporary one.  What would I do?

Dreams have a way of always resurfacing. One day I stumbled upon Trisha Leach and her podcast Keep Your Daydream Alive. She was just getting started and had only a few episodes at the time. Episode 3 highlighted “SV Delos wants to make you smile!” As luck would have it, they had a YouTube channel and the hook of my childhood was set.

Growing up in Chicago, the view of Lake Michigan always seemed to draw me – to the sailboats in the harbor. I wondered at the places they might take me. The destinations and exotic places that could be enjoyed far from those brutal, windy winters. But those were only dreams.

Later, after college I moved to Houston and quickly discovered Clear Lake. After marveling at any suggestion that the water is actually “clear”, there were those sailboats again. Only, these had direct access to the Gulf of Mexico and the oceans beyond.

After binge watching SV Delos, WhiteSpot Pirates, Follow the Boat, DrakeParagon, and stumbling upon Annie with Have Wind Will Travel and her books…the search started for me to really understand what a sailing life might cost and if it was even possible.

Inspired, this is what I learned. Yes, not only is it possible; but it is not really out of reach for most citizens in the USA. In fact, many people are already living full time on sailboats and doing so for about $1,000 USD a month.  This has been confirmed recently by Gone With The Wynns where they average $916 a month in the Bahamas.

The best part, living on a sailboat is like the ultimate tiny house.  If I want to change location, just hoist the sails and go!  I can “live on the hook” and avoid any parking fees. This opened the entire world to me!  No need to keep a house back home and a car if I cared not to.

At this point it seemed everywhere I turned on social media all I could see was sailing, sailing sailing !

But how will I get from here to out there – and sailing?  And can you do it too?

Started with a question…

Maybe I was depressed and in a funk. Could have just been that I was tired and bewildered. Then again, it could have just been born in frustration. Does not really matter. All that really matters is that I asked the question, “what makes me happy?”

You may have felt and thought what I was at that time yourself. Each day….felt like I was living that Credence Clearwater Revival song:

Well you wake up in the morning you hear the work bell ring
And they march you to the table to see the same old thing.
Ain’t no food upon the table and no fork up in the pan.
But you better not complain boy you get in trouble with the man.

The attitudes of entitlement, not thankfulness and appreciation and love from others. Take the money, turn the back. Something must change.

The lie we are told is that if we work hard we can be successful. Earn a rising income. Buy “stuff” that will make us happy. And enjoy the good life. But what we really find is that we are in debt on a wheel that never ends. By the time “retirement” arrives we don’t have enough money saved so we continue to work postponing the dream…that never arrives.

I decided my situation would be different. Enough with working exclusively for others – government taxes, the non taxpayers, bailing out other’s bad decisions with nothing left over. Don’t get me wrong, I am not talking about being selfish and consuming everything on myself. I am saying stopping the nonsense that enslaves me (and you) to others. I wanted freedom to pursue passions that made me happy.

What makes you happy?  What makes me happy?

The decision of what to stop doing was easy…no more debt. No more stuff. Downsize my life. Eliminate everything that provided an obligation to someone else on my life. An unwanted divorce made this much simpler. Realizing that I am not responsible for another’s happiness provided a good start.  But I realized that things only enslaved me.  A house, for example, is not mine if I don’t pay the taxes each year or neglect to make that monthly mortgage payment.  Ownership is a hidden rent on the future and makes me a slave to the taxing authority.

Then my attention turned towards what makes me happy?  Not what to eliminate; but rather, what I can or will do.

My career as a traveling consultant provided an escape. It challenged my intellect.  Traveling meant that I lived in hotel rooms. Everything I needed for a week is carried a suitcase. I realized, evenings exploring whatever city I was in provided great joy. Watching. Experiencing. Smelling. Hearing. Tasting. It was the simple things – many just requiring two legs to walk and see. No bitching. No moaning. Making friends after a simple “hello”. Helping others because I wanted to, not out of necessity.  Stuff no longer mattered.

What makes me happy? Traveling with curiosity and purpose. Learning. Becoming aware. Asking Who? What? Why? When? and How? Deep and meaningful relationships.  And fitting all the abstract pieces together into a wonderful fabric of experience.

What makes me happy? This question led to the next …toward what would I change my life’s direction? The key word is “toward”. That would change my journey. The Roadmap. Compass heading.   Object on the horizon.  Toward what?

Where is your journey taking you?

Beginning…where to start?

This journey has really started to take shape about three years ago – having turned 50 years old, kids were starting to complete college. In the last two years the picture of “retirement” really started to take shape. It became tangible in February 2017 when purchasing a sailboat and paying that first month of slip rent.

In sharing this journey my hope is to inspire others to live beyond our own self-imposed limitations. This is a lesson I am really learning – identifying the handcuffs I’ve placed upon myself through my own thinking. These are not “real”. They are just negative thoughts saying internally, “I don’t know how to do that”, “I couldn’t possibly learn the skills required”, or “that would be so embarrassing if I fail.” Personally, I am more interested in pursuing the possibilities of sailing and learning and avoiding saying “no” to myself.

One reason for this blog is to share a firmly held belief that none of us needs to be “rich” to pursue making a dream of living full time on a sailboat into reality. Of course, the more money any of us have provides greater options; but, it is not a requirement. So I set a personal budget to see how to accomplish this on a typical social security income using the USA as a benchmark.

Over the past few years I have come to set a big-hairy-audacious-goal to sail non-stop around the world – starting on the first day I retire. Well I better get started now! I have never sailed before so I am a novice. But there is no better time than the present to start. This may be crazy, but I am determined to accomplish this goal. But each of us needs to set our own vision and goal and not feel pressured by someone else.

This blog is not about making money or vain glory in how many followers subscribe. It is a tool to discipline myself and share. I will be documenting the journey and providing resources to you through this blog. If you are likeminded, please join along. I look forward to calling you a friend.