Sailboat Considerations – Happy Fathers Day!


For a short while now, about 20 years, I have been considering life on a sailboat. After getting out of the Navy I started looking at sailboats instead of a house. My father convinced me (rightly so) that a house would be a better investment at that age. Four or five houses later I call my father ready to pitch my business case and justifications for a boat again… because … it’s Dad(!) no matter how old and individual I am, for some reason, it always matters what he thinks…

“I’ve been thinking about a sailboat again. In a year or two, move onto it,  rent my place out for a little residual income, possibly sail over the horizon after T is done with High School…”

Pregnant pause…

“Yea, I think that is a really cool ideal. You should do it before I get too old to come help!”

My jaw hit the floor. I was silent. I think he sensed my jaw agape from 2000 miles away in AK.

“It’s a really good ideal!” He follows to encourage me that it’s not a trap. HA!

We talk for a while about some of thousands of boats he has owned over the years and how he always wanted to sail the world.

B – circa 1980 (4yrs old) with first fish, caught at Lake Kelly, AK. In the background is Dad’s 1970’s Grumman Aluminum Canoe,  rigged with a sailing kit.


For the past year I have been working on refreshing skills needed aboard a ship but more than that… obsessing about details of what I would need/want in the way of a boat. Being such a methodical dreamer/thinker; I put together a list of things I want from a boat to assist me in purchasing of the right boat.

What I like or want on a boat:
  • Walk around room on deck
  • Steps off stern (sugar scoop)
  • Center Cockpit
  • Ketch Rigged
  • 40-50 ft
  • Water maker
  • Larger (cruising sized) fuel tank
Optional or add later:
  • Solar or stainless arch in back for solar
  • Bow Sprit
  • Dodger and Bimini top
Possible ships; presently on the market (bench-marking):
  • 1987 Baltic 38 DP – $98k
  • 1984 Amel Maramu – $75k
  • 2008 Beneteau Cyclades 50 – $137k (PR)
  • 1983 Bruce Roberts Custom Centercockpit 55 – $149
Loan Options:
Essex Credit – 100-149k @3.99% 144 Months – 2006 or newer
Essex Credit – 100-249k @4.29% 144 Months – 2006 or newer
The financial part of this looks much more appealing than buying real estate. With net positive cash flow from existing investments my monthly cash flow could allow me to pay off a sailboat in just a few years (a fraction of the actual loan terms above).

Mostly what I want from a boat is freedom from the frantic pursuit of the modern American Dream which has been mutated to mean a bigger house, newer car, 2.5 kids, work promotion, a larger desk/office at work, and daily evening programing… aptly named as corporations program the public to want more from the super-consumer lifestyle created for us. As I walk the dog though the hip/affluent parts of my neighborhood each night I see the programming in progress. Every house with a blue glow emanating from the front room and families staring into the programing screen. Our focus on the purpose life is no longer in alignment with experiencing our lives. Traffic, work, traffic, kids/home, repeat, maybe the occasional vacation package for predetermined experiences to be posted to show all how interesting your life is. I want escape from spending the rest and best years of my life chained to a desk ensuring that shareholders build wealth while more often than not the producers are under compensated. I want less things and more time.

Don’t get me wrong…Not being independently wealthy (and failing at my ongoing search for a Sugar Mama) I still need a job. The job is what has the potential to fund this kind of endeavor and I do hope to continue some kind of work, though I do want that job to be completed in a more asymmetrical way.


YouTube is the ‘frenemy’  as I watch people joining the sailboat cruising community ‘come hell or high water’. Their struggles, pains, and hard work are well documented.

Starting out

Balancing against hard times is the beauty, real freedom, and amazing adventures that can be had.

Real work / life balance! 🙂

Will this flicker become a flame? Who knows… I could just be dreaming. Encouragement from a father that wants to live vicariously (and many friends) keeps me hopeful … stay tuned!

3 thoughts on “Sailboat Considerations – Happy Fathers Day!

  1. Like you I am in the process of buying a sail boat to live on. My goal is to only work 6 months a year, and try to just LIVE the rest. My boat of choice would be an Islander Freeport or an S2 11.0A. Either could be purchased for under $40,000. Another $10,000 or so and your good to go! I have already sold everything I owned and I’m saving all I can to buy it outright. Wish me luck!

    Liked by 2 people

    1. Much luck! I love that plan and maybe you can help crew on the bigger passages! I would not be able to single-hand a big boat on big transits. I’ll keep an eye out for your updates! 6mo work life sounds about right… I was thinking consultant work paying double but working 1/2.

      Liked by 1 person

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