The Offshore Voyaging Reference Site

A House That Makes Me Think About Cruising and Life


Funny the triggers that get me thinking about larger issues. A few weeks ago, while we were visiting Bermuda and out with friends on the water, we passed the house in the picture above.

It’s a pretty nice house. It shares an island in Hamilton Harbour with several other private residences. It has a small private beach, a nice wharf, palm trees, great views, two moorings, and a berth at the yacht club to use when going ashore. It was built about 25 years ago to traditional Bermuda design by a guy who was born and brought up in Bermuda and loves the water and sailing.  It even has a nice workshop.

Now, I used to have a real problem looking at this house. In fact, if I passed it, I used to stubbornly turn my back. You see, that house used to be my house.

A Typical Boomer-Cruiser Story

No, I wasn’t rich. At the time I bought the land, property on an island was valued at half that on the main road-served islands of Bermuda. And back then, building costs were still within the grasp of a guy with a small, but reasonably successful, business.

When I moved in…well, I figured I had a paradise and would grow old there. But five years after I built the house, I sold my business. No, I still wasn’t rich, but I had enough money to buy a nice boat and go voyaging.

I rented the house, which financed our day-to-day expenses. I figured I could go voyaging for a few years and then I would go back to work. And I knew I was incredibly fortunate to have that chance in early middle age.

Along the way, I met a wonderful woman named Phyllis, but that’s another story.

Reality Time

After six years Phyllis and I returned to our paradise-house in Bermuda. Time to grow up and get real jobs, we thought. Voyaging was over, at least until we retired, and that wasn’t coming any time soon, what with taking all that time off in our best earning years.

Or Not…

But it wasn’t long before we both started to pine for the freedom of voyaging. And since this was early in the millennium, when property values were near their peak, we had a choice: Keep the house, get real jobs, and work on making enough money to have a secure old age; or sell the house and keep voyaging, with the attendant risk of spending our old age shopping in the pet food aisle at our local food store.

And, of course, you all know what we did.

And now you know why I used to have a hard time looking at that house. It just hurt to see what I had given up. But you know what? This last time we were in Bermuda, looking at that paradise-house didn’t bother me at all. I guess the wonderful freedom of the last 10 years, together with the hope of more adventures to come, just outweighed missing the house and a lifestyle we will never be able to afford again.

Life Lessons

Don’t get me wrong, this is not a long lead-up to tell you what you should do to go cruising. You need to do whatever works for you. But this is what we have learned from that house that seems to work for us:

  • Just because one of the choices in a life-direction-decision is really hard, particularly at the time, doesn’t make it the wrong choice.
  • We will always trade great possessions for great experiences.
  • In the end that house would have become a “beloved prison” for Phyllis and me: Continuing to own it, with all the attendant expenses, would have nailed us to jobs, whether we liked them or not.
  • Due to the decision to keep voyaging, we will probably never be completely retired, but that’s OK. In fact, we like working.
  • The risk to our old age security was/is worth it. Although ask us about that again, if and when we’re tucking into a can of Alpo!

Be Careful

I said I wasn’t going to preach about what you should do, and I’m not, but after saying all that, I would be remiss if I didn’t add a warning caveat:

If you are going to make these kinds of decisions, you better know what the numbers are. We developed and maintain a very detailed life-spreadsheet in which we analyze and project, as best we can, our finances over our expected lifespans. And we try to modulate our expenditures to reflect the ever-changing reality of the world around us—I say “try” because it ain’t easy. (Those with properly funded defined benefit pensions don’t need to be quite as diligent about this as we try to be, particularly if said pension is indexed.)

Bad News For Voyaging

One more thing. I wonder how many of the voyagers out there are at least partially financed, as we are, by house-related equity or rental? I have no data, but I’m going to guess it’s a huge percentage, maybe better than half.

And For Young Aspiring Voyagers

And that’s really bad news. You know why? Because, on average, young people just don’t have the opportunities in property, or much else come to that, that we boomers did. And not only are they struggling to build some house equity and savings in the recession-that-never-ended, most of them are going to need more savings than my generation does because very few of them are going to have a defined benefit pension, like many cruisers have.

When I look around I ask myself, “How in heck is any thirty- or forty-something person, unless born to money, going to get the assets together to go voyaging?”

A Glimmer of Light

I only see one advantage they have over us oldsters: The advent of the internet has made it possible to work from just about anywhere. So, if I was an aspiring cruiser, I would be acquiring every skill I could think of that could be practiced over the internet. Maybe that way a young person can work and voyage too.

Sorry, younger aspiring voyagers, that is the best I can think of to help you get out there.

And, by they way, I’m not real proud of what we boomers have handed over to the generations coming along behind us, after our watch in charge. Particularly the way we have let income inequality skyrocket in much of the world.


OK, I know that I wrote some controversial things here, particularly in the last part, that may upset some of you, particularly in my own cohort. And you are entitled to your own opinions and to express them in a comment. Have at it. But please keep it nice and don’t bring political parties, politicians, or national agendas into it.

I would also respectfully suggest you think twice before making comments that start with sentences like “the trouble with young people today…”. Positive suggestions about how they might get out there voyaging would be a lot more constructive…and might keep your children talking to you too!

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