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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We have followed the same course – and I routinely drive by the old house and smile – having enjoyed having it – and even enjoyed selling it – albeit at the bottom of the market! We’re now cruising 6 months on, 6 months off – looking after snowbirds houses as they travel south for the winter!

As to the youngsters… Fortunately, most youngsters are probably much more resilient than the oldies – and prepared to put up with much less – smaller, older, less equipped. That is at least in their favor for getting out there and experiencing early…
They are also normally somewhat more impatient, so I doubt the cruising life is something that they would adopt for a long time. A couple of years is probably about all they’d want – so again, makes the whole prospect a little more manageable.
We all (nearly all) have had to contribute our part to this world – and the youngsters need to also. The work ethic is not dead amongst them – just a little hidden perhaps, such that if they get out there and cruise a little before going to work seriously, it may spur them on to work very seriously (to the benefit of us all) so that they can afford to get out there again in later life – once they’ve slowed down some…

Marc Dacey

John, this is refreshing frankness on your part.

I suspect I’m about 10 to 13 years younger than you. I’m either in the youngest of the boomers or the most elderly of the Gen Xers. I’ve been following a vast bulge of boomers “in front of me” in terms of employment my entire life. It’s part of why I went fully freelance in the late ’90s…there was always a fractionally older and more experienced person waiting for an interview. It’s also why I bought a house in the late ’90s…I knew that was our “golden ticket” to staying in the middle class *at all* and might eventually help to finance cruising, which we might as well do sooner than later, because I have rather serious doubts that I’ll ever seen any sort of pension apart from my own savings, or that I’ll live longer enough to reach the retirement age of 85 that is, mark my words, coming soon. My wife’s a mere 39…hardly anyone was born in 1974 in Canada, so her future in terms of pensions is even grimmer than my own.

No wonder we want to go sailing!

Anyway, we are keeping the house for rental property while we sail for the very simple reason that if we sold up, we could never again afford to live in our home town of Toronto. We could buy three small farms (or a used Swan 53, maybe) outside of town, but the house prices are insane. As insanity goes, however, it’s made a great, if judiciously used, lever by which to pay for refitting our boat. Tenants already pay down the smallish remaining mortgage, and a second set of tenants when we move aboard will put a dent in the diesel and sail costs.

So there’s an upside to retaining a house, but it helps if you think of it other than as a home, and more like a dividend-yielding investment. If I want a home, I’ll have to move down East, where houses cost less than Toronto garages.

Erik de Jong

I can probably be considered to be one of those “youngsters” myself, and can actually confirm that there are still plenty of ways to get “out there” if that is what you desire.

One needs to get creative and make life choices that might not be the most common or obvious choices, but it is for sure “doable” and very enjoyable I must say.

Friends of mine (also youngsters) became professional delivery skippers/crew and get paid for it while seeing the whole wide world.
I know other youngsters that offer themselves as “on the road” handy mans and do all kinds of restoration and maintenance jobs on boats of people that are already out there.
Or young couples that sign up for charter companies to become professional charter skippers.

I chose the way to reduce cost by learning anything I possibly could about boats by becoming a professional boat designer/builder and build my own cruising boat and save huge on purchase cost while creating a product of which I know it is actually more trustworthy than what comes from most shipyards these days, and that should easily outlive myself.

One should not wait for the stars to align properly, one should adjust ones position in life to make the stars align properly to suit your needs.

If you really want it, there is a way! It might not be the easiest, or most convenient, or most conventional way, but there is a way! You will have to make compromises though, a house like the one in the picture, is might as well be on the moon for me, it will remain unreachable!

Tom Chapman

Poverty is freedom

Marc Dacey

There’s wisdom there. I think my yearly cruising budget of $20-$25K for two adults and a teen on a freshly refitted boat is doable and actually allows for “treats” (like the occasional dock visit), but a lot of people think it’s the breadline budget and wondering where we’ll find floating dumpster from which to eat.

I also agree with Erik’s “just go for it” tenet…if you want it badly enough, you’ll be willing to live a fairly itinerant lifestyle to gain all sorts of experience on the cheap. The only warning I would suggest to any younger people willing to crew is to make sure you look as hard at the skipper as the skipper should be looking at you. I’ve heard some fairly bad stories about “Cap’n Bligh” types with hired crew.


First off I would read Anny Hills book voyaging on a low cost budget with a grain of salt. Also consider Atom Vayages (just use google))…then 20 small boats that can get you anywhere by Vigor. Given that the boat market is at an all time low there are great boats to be had in the classic plastic category. A friend recently sold his Alberg 30 complete for 1500. Pressure sale to get out from under it. If you do a complete refit and go as a minimalist and learn to do the work yourself well it can be done for under 10k. Combine that with six days on the hook if coastal cruising and one day in a marina a monthly budget can get very low. Have friends on the west coast of Canada who are very resourceful and cruise and live on their boat for an average of 300 a month. When they plan a long voyage they either barter or work at anything they enjoy till the boat and kitty are ready. Typically 3-4 month.

What I learned from such voyager / cruisers is the boat selection is important as it will suck up most of your budget. Classic boats are a very realistic and affordable option provided its a true blue water boat. Maintenance is important and the more your learn about the vessel and maintenance the less expensive it gets. A vessel is nothing more then a set of systems combined to make a sailboat. Learn each system and its components and your seamanship skills will grow exponentially. And operating costs will drop. Finally consider a minimal outfitting. No hot water no reefer a top quality mounted VHF one handheld three GPS units one mounted compass on deck one below and one hand held. A self made drogue from a kit a good dink you can buy or build with oars as exercise is good upgrade to an outboard as budgets allow and a reasonable selection of ground tackle. Replace or refurbish the standing and running rigging and your almost done. Clean and primp her only to the level that you are proud of her. Younger folk can do it if they have the desire and many do. They just need a gentle introduction and good mentors such as this site and many other. Of course having cruising friends help as they walk you through the steps bennefitting from there experience as crusing is very much a community activity. It can be done on a small budget even if only seasonally at first to gain the practical skills needed if you are willing to make the tradeoffs.
Example. Fill a 5 gallon jug of water turn off the toillet water supply and use only that water and see how long you can make it last. Then go fill the jug at a friends house and bring it home. Many valued lessons will be learned in the safety and comfort of your own home. Enjoy the experience.

RDE (Richard Elder)

Hi John,
I can certainly appreciate your desire and efforts to not allow AAC to degenerate into a forum for expression of “political” views. Especially when politics is commonly seen as emotionally held adherence to fan clubs that call themselves democrats, republicans, liberals, NDP, tories, labor or whatever.

However, important events and public policies that directly affect the health of our oceans and our financial ability to choose to be sailors are deeply connected to political choices.

-Ignoring the relationship between climate change and sub-sea methane release does not make it go away.
-Loss of coral reefs through ocean acidification from Co2 absorption changes the nature of the undersea world treasured by many cruisers.
-Strip mining the sea bed of all merchantable sea life does not create a viable Newfoundland cod fishery.
-Burning coal to power the economies of China and the USA does not reduce the concentration of Co2 in the atmosphere, and denial doesn’t change physical reality.
-Financial ruin of the middle class and concentration of wealth in the hands of .01% of the population populates marinas with megayachts while keeping the cruising dream out of reach of people living paycheck to paycheck in debt slavery.

Determining the best course for AAC is not an easy line to walk. But censoring out the controversial is in fact a “political” decision in favor of the status quo.

Svein Lamark

Hi John!
I do admire you and Phyllis after reading this. I wish you fair winds!

Ray Dunn

Great reading- and great timing! Seems these past 5 years have passed quickly since moving from Tucson to Charleston, and my wife hasn’t left me, the economy is slowly coming around (for now) and we’ve moved from dinghy to J24, to the current Olson 30. I’ve bugged Colin enough about Ovni’s to settle at least some of our questions, but looking at the big picture and long-term voyaging, I think Richard is correct. Some of those concern me more than others, but as my retirement nears (~ 7 yrs), I wonder if I won’t blow too much on the new boat and need to re-enter the work force after we get back, or delay our departure. All of that is still up in the air, but “choose wisely” is definitely our mantra!



Very timely discussion for us. Although rental property did enable us to ‘retire’ earlier than most, I would hesitate to recommend it to others. While great little revenue generators when you’re there to maintain the properties and choose your own tenants, once you hand over day-to-day management to a third party and you become remote landlords, there is a
distinct possibility that enjoyment of your voyage will be greatly reduced. The management fees will take most of your income and every little repair that you could have fixed in five minutes for free will now cost you $$$. We often found it more cost-effective to fly back to Canada to paint an apartment, fix a leak, or whatever, rather than paying somebody else hired by the management company.

The worst part is being in some beautiful place and receiving an email, or, worse, just anticipating the next email reporting the newest problem.
I distinctly remember being moored at the snout of the Svartisen Glacier in Norway on a beautiful, crisp, moonlit autumn night and there I was, on the deck, on the satellite phone, trying to deal with some problem or other. The glorious surroundings just made it seem worse.

Recently, three days after making the decision to sell up, we found we’d be named in a ‘slip and fall’ lawsuit where an intoxicated ‘friend’ of our tenants fell down the stairs and broke a leg.

The quality of the tenants, the property, or, the maintenance level doesn’t make any difference. Issues will arise for which you cannot prepare yourself in advance.

Being in the group without a pension, we’ve had to make our own and haven’t done too badly, however, the uncertainty of how long, and if, the money will last is a constant, continual, worry.

As for the young, if you really want it, just ‘go for it’. The Pardey mantra of ‘go simple, go small, go now’ still has merit.

Marc Dacey

If my wife’s brother wasn’t a professional superintendent, we would have the same reservations, and would probably just cash right out of Toronto. We would prefer to avoid that, but it’s a decision each cruiser/landlord-in-absentia has to make for themselves.

We have actually considered having our 20-something nephews taking over our half of the house at a reduced rent in order to maintain a “live-in” presence…but even though we consider them unusually responsible, that clearly comes with its own hazards.

Seriously, though: first-world problems!

Marc Dacey

I get people in the middle of winter knocking on the side of my cradled boat, probably wondering if I’ve stick-welded myself to something (due to the sailorly vocabulary, perhaps). They ask me if it isn’t hard working on a cold boat with only an old radio and a space heater as amenities. I usually reply “if my biggest problem today is ‘fixing my other yacht’, I’ve clearly got a shortage of trouble in my life!”

I find it helps to recall this when I think how modest my parents’ means were, and how long it took them to feel even remotely financially secure. The whole “boomer” phenomenon of widespread prosperity is the blip…what came before and is back again is far more the historical norm, alas.


I know only one person under 35 who has a pension. (She’s an Ontario teacher, and teachers here pour 10-12% of their take-home pay into an independently managed pension plan that is widely regarded as among the best run plans in the world. The most reliable investment strategy in Ontario is “do what Teachers does”.)

None of my friends in the private sector have a pension, not even one of those “defined contribution” things that are really just a market investment, not actually a pension.

It is not surprising, then, that there is a lot of support among my generation for tripling the contributions and payments of the Canada Pension Plan.

That said, I think it is still possible for someone fresh out of high school to get enough financial independence to get out there cruising by their late 30s, but it means some lifestyle changes:

– Train hard for a field that is in high demand. The skilled trades, engineering, and parts of the health care sector seem to be good bets right now. Having some skills that will let you do some work online while travelling is certainly not a bad idea.

– Own, not rent, a modest house in a not-too-big city. The cost of living in Toronto makes it very hard to get ahead. But not far away in Kingston, where a decent 1200sf home is under $175k and you can get anywhere by transit for $65 a month, it’s possible to have both savings and home equity on an apprentice’s wages.

– Skip the unnecessary luxuries. That includes the $80 cable TV package, the all-singing all-dancing cellphone plan, any car newer than 150,000 km, trips to the mall, and weekly dinners out. The difference between cranking the air conditioner, or turning on a fan and wearing less clothing, is easily $600 a summer that could be saved up for cruising (when you won’t have A/C anyway.)

Marc Dacey

Matt, despite owning a house in Toronto, you’ve described our lifestyle, which I term “student-plus”. We bought on a streetcar line and don’t own a car. I wish I was an electrician or a welder, however. Missed the boat there!

If you can stick to your own description, you’ll be out there 15-20 years before me (to judge by your photo), and 25-30 years before “retirement”…which won’t happen for either of us!

Ed B.

Bravo for exposing me for the tethered-to-the-land but dreaming-of-the-sea fool that I am. I long to take bigger voyages than just a three or four week annual jaunt but am just too afraid of the financial consequences and the effect on my family. I’ve acknowledged that it will never happen for me, which if why your site gives me a vicarious “in some other lifetime” hope. I am always pleased to see that others have more confidence and can actually cut the chain that anchors me to the land and just do it.

If I had to offer any advice to the young it would be “Do it now cause it gets a lot harder later.” You can always make up the lost time if you front-load your adventure but jumping off the treadmill in mid-career is very difficult. EB


I loved the article and passed it on to my son. I especially liked the phrase ” trade great possessions for great experiences”. I think some young people could do it with a little help from mom and dad ( if possible). We planned for his education and maybe now we can plan for his sailing dreams. I plan to pass my boat on to him. That’s a pretty good start. We also offer advice to include don’t buy a lot of “stuff”‘, no pets, watch your health, save your money, and find a good woman to share your dreams. He’s on the right track and it’s going to fun to watch him mature. As a side note, he and I leave next May to sail for year. Nothing exotic. Going to start with the Great Loop and see where our boat leads us.

Happy Thanksgiving !!


“Do what you can, with what you have, where you are.” — Theodore Roosevelt
“Live as if you were to die tomorrow. Learn as if you were to live forever.” ― Ghandi
“No man can cross the same river twice, because neither the man nor the river are the same.” — Heraclitus

We don’t voyage as we once aspired, we cruise full time, and we don’t cruise the way we once envisioned (reality persistently intervened). We cruise the way we can, with the boat we can afford, to the places within our reach, and we embrace this reality; we strive to make it the best experience it can be, taking each day as we find it and learning what we can.

If today’s aspirants cannot voyage the way it was once done, they will invent a new way to do it. As you say, the Internet (double edged sword that it is)…

As to today’s young people. They are different. And the river they must cross is different. The outcome cannot be the same. It’s up to them to define their future. Might we have handed them a different river, a better crossing? Perhaps. Might we have delivered worse? Yes.

Nicholas Sweeting

Hi there,

Long time reader, first time commenter.

I am definitely among the younger generation of cruisers here. My girlfriend and I managed to purchase our boat together a couple years ago – both of us were 25 at the time. We spent close to half a year tree planting in Alberta and BC to earn enough for a boat and a modest cruising kitty (assuming only 6 months).

We found the most simple but reliable vessel we could find. A 30 foot steel cutter of George Buehler design, built by a professional boat yard in Florida.

After planting, we ‘jumped right in’ and drove down to North Carolina where the boat was stored. It was in no way easy – we ate porridge everyday for breakfast. Peanut butter and jam everyday for lunch. But we managed – and we were cruising. Don’t get me wrong, there were horror stories – but that’s part of the adventure right!?

After 6 months, we hauled out and put her in long term storage. The boat still waits for us.

The journey did teach me some things.

1. Get the skills to work on your own boat.

For me, this meant enrolling in Georgian College’s Marine Mechanic program. I am on my way to becoming licensed.

2. Get skills you can use ‘on the road’ to make some cash.

Seemed like the above is also applicable here!

3. For young Canadians looking to get out there. Go West, make a buck, get your boat.

We are now based in Kingston. A family ‘situation’ has made us settle for a bit. The boat is going to be shipped up this winter so we can continue working and living towards our dream of getting out there.

We’ll most likely be living off of porridge and peanut butter again.


Matt Marsh

Nick if by Kingston you mean the one in Eastern Ontario, drop me a line sometime. There aren’t too many other boat owners our age around here, it’d be great to get together sometime 🙂

Joe Blowe

Ive been operating a 60 ft 60 ton fishing vessel (hooks not nets) for the past 16 years and have a house that we are enslaved to even though its rented ( being a land lord sucks ), if the current boat didn’t use so much fuel I would go cruising on it, However a sailing vessel is needed.

I would totally do what you guys did and am planning on it, taking the equity and running ending enslavement to the house and the bank, when I’m on the boat I don’t have to get up and go to work I’m already there were ever I am and hope to create that situation on a sail boat though we haven’t quite figured out how yet, we’ve looked at the internet and blogging, travel writing, these thing might suit my wife however I don’t think they’re for me nothing Ive tried on the internet has worked, I find the internet full of people saying give me some money and Ill tell you how to make a bunch (scammers).
I would like to know if anyone has experience with carrying cargo to foreign ports perhaps a vessel that could carry 20 tons of cargo like a Bruce Roberts trader 65 would be a small income, I don’t know I haven’t done it.

I think it would be interesting to hear how different people produce there cruising income.

Pondering our escape from the United States corporation


Very well done! Very familiar.

We like Slick dog food ourselves. It sounds like you are Alpo people. Sail or power – same same.

Life begins beyond your comfort zone. Live or wonder. SF 2012


RDE (Richard Elder)

Two ends of the age spectrum:
Jack Van Ommen, who cruised since 2005 with no income other than a social security pension and no assets other than a 30′ plywood boat. 5o countries and a circumnavigation before loosing his boat in a storm in the Med recently. And by the way, he is in his late 70’s.

Adventures of Alta Pe’ape’a
Young couple in their 20’s who cruised through the South Pacific on a 33′ plywood catamaran that cost about the same as a used car.

Horatio Marteleira

Now I’m depressed. I’m a baby boomer who crossed the Atlantic on my Corbin 39 (and forgot to go back to Canada), I love sailing and living on the boat, as a successful freelance translator I can work anywhere with Internet access, I’m healthy (at least I think I am), and I’M STUCK…and if you can’t guess why, you’re not trying very hard. I suppose one foot on land and one on water is better than nothing. MY POINT, though, is that there are other factors besides money than keep many sailors on a short leash.

Victor Raymond

Here is a young couple who seem to make it work:

Here is young woman doing it on her own. Amazing young lady:

Richard William Lord

Growing up in S.W.Fla., all of my buddies wanted to “Be rich..!!” when they grew up.. Wanting a Volvo, Mercedes, BMW and swearing they’d own one some day.. A big house with swimming pool, big yard, leather couches, big screen T.V.’s, fancy clothes, a wife with a french manicure and implants.. A country club and gym membership.. A tee-off time every week.. European vactions.. Hunting/fishing trips to Alaska with the boys, Carribean cruises with the Mrs. once a year, etc.. Alot of them got what they wished for—–and a whole lot more..

Auto, appliance, home furnishing repo’s, house foreclosures and eviction noticies, bankrupcy, law suits, divorces..Credit cards shut off, credit trashed.. Alimony and child support checks—–(“for how many more years..??.. your kiddin’ me, right..??”)..

Hangin’ out in the beach access parking lot after a full day of surfing, the sun on the horizon and setting—–those were some of the “topics” covered, so many, long years ago—– “What do you want to be when you grow up..??”..

I always felt like a simpleton, sorta stupid when it was my turn to “chime in”.. I’d reply that I just wanted , “To be happy..!!.. And sail to the South Pacific, build a Swiss Family Robinson treehouse on an island, trade puka beads with topless native girls for fruit and finish out my days there..”..

Several would laugh, roll their eyes and under hushed voices say, “What an idiot..!!”.. 1 or 2 though, would look at me, say “That’s it, that’s what I want, too..!!

At 55 and still dreaming of sailing to the South Pacific, trading puka beads, going “off the grid” so to speak, the only thing I could “chime in on” as far as recommendations for “todays youth” is:

1) “Dream big and big dreams happen——if you only believe with all of your heart and apply yourself..” (keep in mind: “What does it profit a man to gain the world, but lose his soul..??”)

2) Be very careful of what you wish for because—–sometimes wishes do come true..

3) Work your fanny off to aquire the “American Dream”, then work your fanny off even more to keep it.. Or—–

4) Slash your overhead, don’t aquire the “earthly possessions” and trappings (read: bills) and keep your life very “minimal”.. (only the very basic requirements), food, shelter, clothing..

5) “Where there’s a will, there’s a way..” If a woman in her 60’s can swim from Cuba to the Florida Keys with no shark cage, (her 4th attempt since the late 1970’s)—can you not also “go after your dreams”..??

6) “Less is more..”.. Keep it simple.. It’s amazing how “little” it really takes to make dreams and desires come true..

Dick Stevenson

Dear John & all,
I suspect that the reality is: if a cruising lifestyle was so great, more people would be doing it. For those who have been “out” more than the first few years of honeymoon period: my sense is that we choose to tolerate a great deal of work, uncertainty and anxiety for the offsetting accomplishment of our personal goals. For Ginger and me that is wandering new countries and exploring history and cultures and meeting new people. That goal continues to remain motivating for us. Other goals may be high latitude sailing in remote, challenging and beautiful terrain while others will want to wander tropical isles, snorkel, dive and fish. It is having powerful personal goals for being “out” there that makes the difference from my observation. The goals do differ, but the work remains the same: a relentless attentiveness to the details that keep you and your vessel safe. It is hard to know what this is like before you live it as it is so very different than shore based life.
My best, Dick Stevenson, s/v Alchemy, London

Brett Anderson

Great post John,

I am an older Gen-Xer who has quite a few years (20) to go until mandatory retirement from an airline pilot career. I don’t ever want to get there. I struggle with the conflict of leaving something I have done since my college years and which I wanted so badly at one time, but I find the passion just isn’t there anymore. The dream career that all my non-flying friends think is so glamorous has become a never-ending succession of long flights to distant lands where I barely have enough time to sleep, eat, and sleep again before heading back. Fatigue, boredom, and frustration are constant companions. The pension I was promised when I signed on to my company back in the 90s was taken away from me by greedy executives who squandered it away and then declared bankruptcy to get out of their obligations (it can happen to any of us, even if you are already retired, so don’t count on a pension if you have one). And yet, while I already have a seaworthy blue-water boat which I live on and no love for my career any more, I still find it hard to cut the docklines.

Perhaps it is a built-in fear of the unknown or my inherent dislike of change. Perhaps it is the fear that I am a one-trick pony who won’t be able to do anything else should I ever need income again. Perhaps it is all the friends and family who tell me how crazy I would be to give up a 6-figure job which many would kill to have. I don’t know where the fears come from, but I do know that posts like yours continue to inspire me and move me, bit by bit, a little closer to my goal of leaving this career soon and experiencing an entirely different life and freedom. Thank you for that.

Dave Benjamin

I’ve been able to live the dream, running the business over the internet and cell phone from the tropics. One suggestion for cruisers who will need to generate income while cruising is to align themselves with a marine supplier who wants some outside sales reps. We contract with people like that and selling sails is a pretty natural thing for a cruiser who has some familiarity with sailmaking. We get inquiries from around the world and most of our customer contact is by email or skype. So it works pretty well for people who are cruising in areas where they can maintain fairly steady internet.


Brett’s post was finally a comment which addresses my perception of the main issues of the very nice openening post… We must afford our retirement, ask someone else to (that is the reference to not being proud of what we left imo), work through it, or hope. Brett exposes the difficulty in even good planning and I would point out to the many mentions of ‘pension’ in these comments that while you may think that your planning is good that the promises of your union or government or banker are sound….they may not be. The major issue highlighted by the feeling that we ‘wish we had left something better’ will likely not be fixed by young folks finding a better work ethic – it will likely be fixed by the watering down of the promise – which when you think about it is fair, boomers asked for and voted for too much for themselves, I am one of them… give preperation some thought too.

Paul Mills


I have enjoyed following this thread, and reflecting on the comments and thoughts expressed.

I am in my late 40’s and UK based. My version has been to take firm responsibility for my financial and professional life. Early on I recognised that working for others (to make them richer….) was not for me. I also recognised even in the late ’80s that the goalposts were repeatedly being changed by powers beyond my influence. So, whilst living fairly cheaply, I worked for 20 years and invested in the things that I could influence. This enabled me to sell mt busineeses and pause for 4 years in my early 40’s. During this time I commissioned and the sailed my dream boat, for about half of each year, with my family and also charter groups; I also figured out what I wanted from the rest of my life.

Last year we moved to a remote part of the W. coast of Scotland, from where I commute South for well paid work every second week. Last month I took areally tough decision. My dream boat having been cost effective for 4 years was now not going to be, and in real terms set to cost £15 -20k per year ongoing. This coupled, with exciting work and a family that are also keen to do other things meant that I could not justify her cost and was afraid if me and my family waking up in 20 years regretting how much she had cost. In due course i am looking at replacing her with a smaller boat, costing about 25% as much to buy and to be based ona cheap mooring – the result of which is that she will only need to be sailed for a month each year to be ‘viable’.

I guess for me it’s about looking forward to what you want, enjoying what you have in the moment…. and also taking time to project yourself a couple of decades into the future – and then look back! . I in no way regret my 4 years sabbatical, and have come out clear about my values and what is important for me as an individual, and the family for whom I have responsibilities.


Dick Stevenson

Paul, I will miss you: on the AAC site (if you participate less) and on the water. Good luck with your new endeavors. Dick Stevenson, s/v Alchemy

Paul Mills

Hi Dick,

Thanks for your kind words….. I will still be around 🙂

Needless to say if you ever find yourself near Ardfern, it would be good to meet up.


Richard William Lord

I swear this site is the best..!!

In my opinion, it’s the new millennium’s, dreaming sailor’s answer to last centuries, “Ringling Barnum and Bailey’s Circus”.. It has thrills and chills, cheers and laughter, boo’s and hiss’s, amazement and disbelief.. Heart-stopping action and unbelievable skill performing under hot stage lights..

So much international talent “onstage” with every post.. To me, AAC is “The Greatest Show on Earth”.. It keeps boyhood dreams alive.. Thanks one and all for the write-in’s and “sparks” for my imagination..

Richard William Lord



Thought your article was brilliant. I am 24 & have spent the last year cruising the atlantic (uk to carib) on a 25ft boat. For me it was only possible by being a freelance skipper- i didnt work and cruise, but i lived on nothing till i could cruise. & now im with a ten year plan so that next time i’ll be able to go sustainably. This cruise i lived off capital, which as you can imagine ran out!
I like that your article highlights how much planning is necessary, and i also like that you highlight how you have to go when you can. Since getting back have been surrounded by older people who could so afford to leave, but their idea of whats necessary to go cruising is so warped-& i think, youve got the house, youve got the pension, youve got the cars! Just go!


Ahh, to be 24 again. I can’t speak for anyone but myself, but an ancient like me (46) needs a boat I can spread out in – cabin camping rather than backpacking so to speak. Point taken, though. You saw a chance and took it, and now no one can take that amazing experience away from you. Good on you! Cheers!


I’ve been lurking around this site since discovering it a few months ago, but never posted. This piece inspired me to chime in. I’ve been a dinghy sailor since my dad put me in a sunfish when I was 12. I got sail training in the U.S. Navy equivalent to ASA 101, 103 and 104 in the late 80’s, and have been dreaming of cruising ever since. Now I’m a 46-year-old bankruptcy lawyer in landlocked Missouri, and I’m starting to take stocks of my prospects for a cruising life at some undefined future date. My chosen career has given me a unique perspective on just how quickly the best laid plans by even the “best minds of my generation” can suddenly go wildly awry.

So, the take away here for me is: (1) start making real plans right now, (2) be flexible, (3) don’t waste a fair wind – pull the trigger, and (4) have realistic expectations. I live in a 40-year-old one-story house in the burbs. Not fancy, but it will be paid off in six years instead of twenty. The house my office is in is a residential house that will be paid off next fall, at which point the “mortgage payments” will be plowed into savings. By the time I am 55 I can sell the “office house” to buy my boat, trade in my home in Missouri for a cottage or condo near my “home port” (my wife insists, I’m afraid) and finance my cruising from income on my savings (very modest, but sufficient). Bankruptcy is a federal practice, so I can take my show on the road without having to sit for another bar exam in case I want to take few cases and earn a couple bucks in my dotage. If The Dream finally arrives in my 60’s, I’ll buy a Baba or Tayana and make the world my playground. If I have to defer until my late 60’s or 70’s, I’ll “settle” for a production boat and stick to the “West Indies”, maybe. In other words, I’ll have alternatives so I’m flexible, but any way life breaks I will still be “on plan”.

It’s damned hard for my pensionless generation, but if you can find a way to live modestly now (without sacrificing the best parts of those all important child-rearing years), it IS still possible to live the sailing dream, I think.

Now, resuming my recreational flying carreer? Yeah, that dream is dead unless one of you dies and leaves me a vast fortune.

Fair winds,

Karl Wulff
s/v Brass Monkey