Have the cruising dream but short on the reality?

This article is for you

NUMBER ONE QUESTION I GET VIA EMAIL goes something like this: What you guys are doing is insane! It has inspired me to quit my job and buy a boat. Can you tell me what I need to know? Can I make some money with a boat?

Discovery in Tonga

Finding places like this in Tonga is harder than you think

I have spent hours and hours trying my best to answer this question for hundreds of people and it finally occurred to me today that I should save myself some time and answer it in our blog so in the future I can just say- read this! So let’s get going. Prior to 9/11 I read there were approximately 200 boats actively circumnavigating.  I would think this number is probably much lower since the economic crisis, as we see very, very few boats out where we are these days (granted we go to pretty remote spots…). But there are thousands who have the dream, thousands who would give anything to go offshore. Why such the discrepancy in numbers?

Plan on spending plenty of time down here

Because the dream is what you find in every cruising article and book (and well, some of our captain’s logs) about sailing: clear starry nights, wind driven locomotion, spectacular coral reefs, fascinating cultures, exotic ports, consistent tradewinds. But they neglect to tell us what pain you must go through to get there. If I had met someone with my experience 13 years ago when I got started and asked the right questions (tough to do before you know what you’re in for) that person could have saved me a world of hurt- emotionally and financially. Now that I know what it takes, what the many hurdles are to turn the sailing dream into reality I can look back and laugh heartily at my mistakes (but the mirror reflects the true story). I would have saved myself a few hundred or so migraines and several zeros in funds that I’ve had to beg, plead, and work for in hideous ways to fund this dream. The proverbial 20/20 hindsight in play. There seem to be as many articles, books, and seminars about sailing as there are about Jesus Christ. But like the difficult to understand 30 something carpenter, none of my research gave me the right answers. What’s it really like to cut loose the dock lines and sail off into the…no, it’s not necessarily the sunset. Want the truth? Read on.

Sailing Mozambique

Things like this happen. Deal with it.

In 1988 I read Tanya Aebi’s story in ‘The Maiden Voyage’ of her incredible solo circumnavigation at the age of 16 and a dream was born. No boat, no idea how to sail? Yes, problem. But I had unlimited motivation and the most important thing- unlimited naiveté. How do most people do it? They work all their lives, save their money, sell everything they own, buy a boat that is ALWAYS wrong the first time (see below), develop a cruising budget by what everyone else says, which they soon learn to be suspect, then if they get super super lucky they then find the ‘right’ boat, which still breaks down constantly, they become discouraged, couples or friends grow to hate one another and they sell the boat at a huge loss before they get 1000 miles into the dream which has become a living nightmare. Don’t hear this too much in the sailing rags, eh? Well it’s true. It almost happened to me. It almost happened to every one of us who are now (sometimes) sporting big grins because we ran the cruising gauntlet and prevailed. We all did it the same way, which I could summarize in two words: hard work. What? You thought sailing was martinis and sushi? Well think again. It destroys marriages, renders bank accounts useless, and feels like nothing the boat broker and your bar buddies talked about in the lead up to your departure. I’ve commercial fished in Alaska, fought fire for a Hot Shot crew, instructed adolescents in the finer aspects of mountain and river travel (who were more interested in playing their Gameboys), and none of these come close to the amount of hell you must go through to go cruising.

Hauling a yacht in Malaysia

Gotta do this once a year- or when you make a mistake

Just a short list to put on the to-do list before departure: 1. Find an “appropriate” boat (as opposed to the “right” boat, which in my opinion does not exist). Time: 3-5 years. People buy the wrong boat for the following reasons: 1) Lack of experience, 2) lack of self-knowledge, and 3) lack of available knowledge. Even when you have none of the above, finding the appropriate boat is very difficult. You will very rarely find your dream house on water at the local marina. Which means travel (expensive), endless searches (time), and brokers (unreliable). Just some of the major considerations:

  • Hull construction, length and design. There are many books on this subject alone. Wood, fiberglass, aluminum, composite, cement, or steel? Unless you have years and years of experience either racing or cruising many types of yachts, this decision alone is a doozy. Ask four people their opinion and I guarantee you will get four very convincing and polar opposite viewpoints. Full or fin keel, narrow or beamy, fast or slow, heavy or light, sloop, cutter, cat, tri, ketch, or schooner? How much room do you need, how much money can you really spend? Rod or wire rigging, teak decks or glass, production or custom, aft or center cockpit, one, two or no heads?
  • What the boat is made of and how “pretty” it is will radically affect how you spend your time at anchor in paradise. Think all that teak is beautiful? Imagine spending a couple days sanding and varnishing every month under the sun’s tropical rays and you might opt for an aluminum caprail instead of wood. Boat built of fiberglass and has a few blisters? Plan on spending six months someday choking on glass dust and inhaling gallons of toxic epoxy fumes. Aluminum? Better keep an eye on those welds in big seas. Steel? A friend of mine stuck a flat head screwdriver right through the bottom of the boat and had to be emergency hauled. In other words, they all have their problems.
  • Equip the boat for offshore use. This will take you a year if you have no job, loads of cash, no life, no dog, cat and a very very understanding spouse. For the rest of us this will take 3-5 years again. Which means by the time you are done, much of the equipment is already turning obsolete and giving you problems because these toys live in a noxious saline environment. Much of this will be done wrong the first time around by yourself or someone you pay (please don’t make this mistake). The equation goes like this: cost will be three times as much as you think, and will take four times as long. This equation is as true as Einstein’s E=Mc2.

Here’s a short list: radar, watermaker, GPS (+ backup), alternate energy sources, SSB radio, VHF radio, EPIRB, liferaft, sextant and almanacs, overboard supplies, interior lighting, safety harnesses, sewing machine, heavy duty windlass, cruising sails, spare anchor and chain… You will need charts- paper and most people these days go with the electronic as well (I have over $4,000 in paper and electronic charts and spend $200-$500 each year on more). SPARES: This is where the novices fall on their face. You’ve spent all this money and time equipping with all the best gear, so why have so many spares? BECAUSE EVERYTHING- EVERYTHING WILL BREAK. This is just a fact. If you have an engine on this boat, you better have a spare for everything: starter, alternator, brushes, injector(s), fuel line, oil and fuel filters (primary and secondary), gaskets, enough lubricants for major emergencies (5 oil changes minimum), fuses, spare wire of all sizes, zincs, ignition, all gauges and senders… How much fuel, what kind of tanks (plastic, iron, steel), how to make sure your fuel is clean after filling from a drum in Baja (we went 6 months last season down one engine due to dirty fuel I picked up in Indonesia which rendered our engine useless- a very expensive and time consuming problem)? And that’s just the engine, which keeps us from spending weeks on end in the doldrums going berserk. You must be able to fix every system onboard or know how to go without. Think hardware store. Think tools. Buy just about everything they sell, because if you don’t you’ll wish you had.

Sailing in Mozambique

Finding places like this makes the pain worth it

2. Learn how to sail WELL offshore. This means more than watching storm technique videos. This means celestial navigation, storm avoidance and procedures, safe seamanship, obtaining and using weather reports (weather fax, email, satellite, cell phone, inmarsat, VHF, ham radio, looking at the sky…) sail handling, absolute confidence and knowledge of your boat, and the most important thing: practice. You should know how to reef the sails in any condition: by yourself with your eyes closed. Diesel repair, electrical troubleshooting, plumbing, rig tuning, energy production and storage (a multimeter should be as easy to understand as filling up your car’s fuel tank), sail repair, hull maintenance. Time: another 3-5 years unless you’ve grown up sailing or have recently completed a Volvo Ocean race. It is very important to learn if you even like it! Which means going ‘out there’ for a few solid long trips, not just around the buoys or out to your favorite day sail anchorage. Or, you can just go for it. Which is what I did and promptly got knocked down off Cape Mendocino, California in 60-knot winds and 35 foot seas. This was an incredible learning experience (albeit costly), but I don’t think it a necessary one for everyone to have. Sailing offshore is simply learning to be conservative. It is inevitable that you will get rocked, but if you’re well prepared it will be humbling and build your confidence instead of terrifying. I’m telling you this because no one ever told me. The pleasures we read about in paradise all exist in abundance and I am addicted to exploring them. I just wish I could have run that aforementioned gauntlet with a little more agility. But there’s an infinitely easier way. Drumroll please…

  1. Go sailing with someone else.  It’s on their dime if something breaks (which it will), and you get to see what works versus doesn’t work on an offshore boat (much doesn’t).  The biggest thing you will learn:  if offshore sailing holds any real appeal.  The reality of offshore sailing has NOTHING to do with the perceptions we all have before going.  Why go through the incredible expense and headaches only to learn you hate sailing offshore?  Happens too often.

There are many boats out there looking for people willing to chip in for running expenses (food, fuel, maintenance, etc.).  This is a great way (and by far the least expensive) to get on lots of different yachts, see what makes a good versus a terrible captain (I guarantee you will see both), a good versus a terrible boat (ditto); how to provision, cook, deal with sea-sickness, plan, navigate, fix everything, stay healthy, and in the end what comfort level you want when you go it alone, which will have a major impact on whether you stay in the black, or bleed in the red.

Hauling a sailboat

Emergency haulouts are never fun

The downside is that there’s a very good chance you’ll get on a bad, or even an unsafe boat.  I meet skippers all the time who don’t think it’s important to have a standing watch at night, don’t know a sextant from an EPIRB, don’t have a clue how to replace a head gasket or rebuild their head.  They’re scared, ill prepared, sometimes obnoxious, frequently cranky, and worst of all:  think they know it all.  These are not the kind of people you want to sail with and this is not the experience to get you off the docks in style. Tips to help avoid dicey boats:

  • Ask a lot of questions (and they should be asking you the same- be wary of anything that seems too easy).   Guys who run ads seeking female crew and in the second interview start to say things like, “and if something happens between us, that would be OK.”  RUN.
  • If you step on a boat and don’t get a full tour of the safety systems (location of thru-hulls, abandon ship plan, fire procedures, etc.) within the first 24 hours- RUN.  There should be a written and well-organized Emergency Station Bill shoved in front of your face as soon as you’ve learned everyone’s name.
  • Look at the boat’s tool wardrobe.  It should be filled like Grandpas shed on the back 40 acres.  In other words, if the captain wants to show you his wine locker before the tool drawer, RUN.
  • DO NOT JOIN A BOAT FOR A MAIDEN VOYAGE.  No explanation needed.
  • Take a close look around.  All boats should be absolutely clean and tidy.  If they aren’t, they aren’t being run safely and you can expect trouble.  Dishes left dirty in the sink?  RUN.

2.  Go with the experts on a blue water passage.  There are several offshore sailing schools out there that cost more than crewing but you will get what you pay for many many many times over.  You will learn which yachts are most suited to sailing offshore, and most suited to your needs.  You’ll get first hand experience handling every aspect of blue water sailing, and you’ll learn it from people who are professionals and competent because they’ve been out there.  If time and money are a factor in this decision (what decision isn’t?), then this option is your only choice.

Discovery in a place very, very few have ever been

3.  Charter a boat with an experienced skipper, possibly through one of the sailing clubs in your area so you can do it with a few friends and have a small fleet of boats in on the fun.  This is always a blast, and while you won’t learn much of the offshore material you will get a better feel for the cruising life, which will motivate you to put a plan into action.  Sometimes the plan will be to definitely stop dreaming about cruising, but better now than after selling the farm (we had a half dozen owners sign up with us over the last 5 years who all had plans of sailing on their own.  Their plans now?  To stick with us and DON’T buy a boat!)  Chartering a boat is by far the easiest, most economical way to have an adventure on water without all the above-mentioned hassles. Finally:  What about turning your boat into a business like we have?  For most people this means chartering, which is much different than our business.  I’ll be honest- I DESPISE chartering and wouldn’t recommend it to anyone.  We chartered our previous boat Saoirse for 7 years to fund our way around the Pacific.  Very, very, very difficult business for a number of reasons:

  1. Unless you are running the same trip over and over again (yuck!) it’s nearly impossible to keep the boat full.
  2. Unless you keep the boat full (see #1), it’s pretty impossible to make money.
  3. Your business is your home.  And you’re going to have annoying people in your home.  You never get any down time.  You don’t get to turn off and disappear.   You’re responsible for your boat and your crew and your clients 24 hours a day.

To me the happiest people I see out here have chosen simple boats that are easy to fix and have the funds to keep it going for a period of time that is reasonable, like 2 or 3 years.  I’ve also met some lucky people who have jobs that allow them to cruise for say 6 months, then work for six months, leaving their boat in a safe place while they are gone (but this creates some very major logistical challenges and obviously impacts your itinerary).  The only successful (which is a loose definition- for the most part successful means covering the cost of the boat, in very few cases it means making money) charter operators I know do the same trip over and over and over.  To me this is no different than working in an office day in and day out but you never get to go home.  I’ve met very few happy people doing this.    So my advice is- be realistic, be extremely conservative, and be suspect of any numbers you draw up that look good.  Number one boats depreciate, number two is that they cost a LOT of money.  Every time you sell a trip you’ll be putting the money right back into fixing something. People ask me all the time why we’re doing this.  How could it be good enough to leave everything else behind?  In the first couple of years (and even now there are times) out here I probably would have looked a little cross-eyed and wondered myself while blathering something about living the dream (LIES!).   But now that I’ve taken my turn in the school of hard knocks and done just about everything wrong a few times, the rewards are so great I can’t imagine doing anything else.  I’m just thankful I don’t have to do it all over again! If you would like to contact me for more advice or ideas on how to get out there, please leave a comment, or get in touch directly http://www.offshoreodysseys.com/contact/.  I am also available to consult on any of the above subjects for a fee for specific needs or requests, or if you would like direct supervision on purchasing a yacht, or starting a business like The Best Odyssey.

In closing, I’d like to leave you with a couple of colorful (and I think pretty accurate) quotes:

“Don’t buy a boat.  You don’t love boats, you love the idea of a boat.  The reality is, it’s just a drain on your time, your wallet, and your emotions.  In the end, she will break your heart.  You want to feel pain?  You’re better off slamming your hand in a car door.”  — Author unknown

“I believe that marriage and sailing are fine institutions.  And Institutions are for crazy people.”  — Author unknown


  1. Great piece Honey! Love your honesty. Am so proud of you for hanging in there to the end of the commitment. Mom

  2. HI
    I am a private yacht captain , a couple of years ago I was docked in Bonaire when you came into the marina , for some reason I didnt introduce myself , I think it was a mix of jealousy and fear for what lay ahead for you

    Respect ,you have managed to find a niche within a niche , lots of people ask me when i will get my own boat , one trip to the chandlery for the normal this and that and the concept melts like a block of wax on a rental cars front seat in the caribbean

    I digress , great job , have enjoyed following your travels
    Fair winds

    • Wow- what a great comment. Seems like another lifetime when we were back in Bonnaire. If you run across us again definitely stop in- always awesome to spend time with other ocean fanatics. It has been a hell of a run on all sides- fun, fear, torture, bliss, highs and lows of course. Wouldn’t trade it for the world, but it has surely taken some years off my body!

      Thanks again Fouche.
      Captain Gavin

    • The one from way up was taken from a paraglider in Tonga (we have a tow winch we can put in our dinghy). The one with the reef right next to the boat was taken from the top of the mast in the Marshall Islands. Both were taken by Jody (www.jodymacdonaldphotography.com), our photographer. Haven’t had tooooo much trouble with reefs (or at least not in these shots!).



  3. Enjoyed your article, thanks for writing it.

    I have a 1968 Coronado 25, S/V Spritzer, in pretty good shape. I”m looking at a Roberts 53. It’s just a bare hull, so it’s pretty cheap, but it’s what I’m looking for to take across the ocean. Being blank on the inside, I can customize her for my personal needs (I’m a woodcraftsman and home remodeler).

    Just started sailing, taken ‘Spritzer’ out 5 or 6 times and I love it.

    I wrote the small story about my initiation into sailing – the bug that bit me drew blood, literally – and iv’e had the curse ever since. Guess I always will.

    Living on the Coronado 25 and it’s cramped but absolutely wonderful! Never been as happy living anywhere else.

    When, and if, I get my blue water boat I’ll look for you guys out there. Since there are only two major seas, I’m sure we’ll run into each other at some point.

    See you then.

  4. Your blog is pretty interesting to me and your topics are very relevant. I was browsing around and came across something you might find interesting. I was guilty of 3 of them with my sites. “99% of website owners are committing these 5 mistakes”. http://tinyurl.com/d8r7ejo You will be suprised how fast they are to fix.

  5. Pretty great writeup, G.

    The name of my boat is Madness, I think you undertand why. I was one upped by a boat named “Fine Line”, presumably the fine line between Genius and Madness; that describes cruising even better.

    I lways laugh when I see a boat named Tranquilty. If not for the mild profanity, I would name a sailboat “Tranquity my ass”

  6. If you “sail” a floating condominium with two big engines, well then, you are going to have to pay the price for all that comfort.

  7. This information is right to the point and backed up by real experience.

    I’d like to add that the dream can also be a teflon-easy transition, like mine was, with the proper attitude and preparation. I think it is the tendency for most who are new to the dream and inexperienced in many facets of it, like boat choice, to get in over their heads way before they launch. Nothing will wreck the dream as fast as “no money”.

    While it’s nice to have a new Hans Christian 33 at the price of oh, 95k, it’s too big a transition to buy an expensive boat straight away. So buy cheap, and if the whole deal goes south, no big deal. I bought an Endeavor 32 for 4 thousand bucks, with a newer Yanmar. I was lucky in finding a great deal, but I had been looking for a couple of years. I knew nothing about diesel, so I bought the book and studied. So far I’ve been cruising the Maine coast in the summer and having the time of my life. Being a life-long sailor is an advantage–certainly–

    The best place to search for a good deal (and there are a TON of them out there), is to search for a boat where there are LOTS of them–in coastal areas, on CL, in boat yards, and by advertising on CL. Many boats sit around accruing yard bills (like mine was when I found her) and are sold for a fraction of their true value. Start the search and look at a few dozen boats. When you make an offer–low ball it. The guy wanted 11k for my boat, which was worth the price. I offered four and forgot about it. A week later, he called and said ok. Yours may be the first offer in a long long time. Then forget about it–if you don’t get the boat, there will be others. Hundreds of them. Be patient. And go simple! Avoid lots of systems and do-dads. Do lots of overnighting in protected waters before you go to bigger water. And don’t forget the 7 P’s of the United States Army:

    Prior planning and preparation prevents piss poor performance.


    I immigrated from Switzerland to Vancouver Island, Canada some years ago. I was a very experienced sailor on the largest Lake in Europe, (we don’t anchor over night there), have no ebb or Tide and with that no bad surprises, or even currents. When I bought my first Sailboat in Vancouver, the seller took out all good gear, paper- and electronical Charts and the Hunter-Brooker did nothing. I ate dinner at a chinese fellow, saw his napkin, which has had printed on a small, old navigational print from old, sunken sailboats from the 17th, 18th and 19th century. I used this as my ‘chart’ had nothing else and left for Campbell River. When telling my Story 2 years later, when I made the Coast Guard Program, all where laughin. Off yourse there is much in-and-between, as I needed to get rescued, in nice weather, an engine not working, no wind and a 8knot current driving me towards the rocks, a captain calling in asking me about ‘bleeding the engine’. Me, speaking swiss german, knew the words ‘BLOOD OR BLEEDING only in regard of real blood, answered him that I do not understand why I should hurt and cut myself. It’s the engine that Needs help not me. Then the coast guard called me on VHF and asked me where I was, I said that I am REAL CLOSE TO THE ISLAND WHERE IT NEVER RAINS. I completely forgot where I was, while my wife was yelling at me, that she is dying because of me. When the coastguard called again, asking what my boat Looks like, I had to ask my wife to put her head out the hull and look up the colored stripe. When she did so, an orca just put his head out the water just in front of her. Again, she yelled at me, that she is being almost eaten now by a large fish, with a head so big it could be my mother, all the while she yelled and sweared at me. learned real fast about sailboats and the lingo. I came out with 99% on all my boating tests and yes, after that I went out in storms, at nights and just about in any condition allone. I have learned, that me shin will always hurt, that me wife is not made for sailing and that others will be there for you, same as I am there for others and most of all, ask and you will receive answers. Don’t be a Snob, or arrogant and learn from your misstakes without giving in to fear. Have respect of the sea, towards others and try to maintain your own boat.

    Cheers Andy

  9. Perfect timing. While your article goes to the jugular, you did not mention anything I have not taken into consideration, but rather sums up the process. I am done with the 26’er and want to move to a 35-38 to expand my sailing adventure to full time. After two years of boat searching, I have hit a wall. I am worn out from traveling to see used craft that are nothing what their pictures or descriptions show. I am worn out from proud owners that think their 30 year old boat is worth $15K more than it really is. I am worn out with ‘misinformed’ brokers to use a kinder word than most that come to mind. Your article has given me personal permission to step back and take a break. To promise myself not to open the well-worn websites first thing when I wake. I think I know the outcome will be a hole in the water in which I throw all my money, but for now…. a deep breath and a step back. Thanks!

    • I have been remiss in responding to your comment, huge apologies. These get lost in my email. I certainly understand your frustration with finding a boat! Good luck, hope the horizon becomes a reality!

  10. Oh I must say all of you answered a lot of my questions, I truly do want a sailboat to go up around the New England coast , charleston area. My dad kept us on the water nearly all of our lives I miss the smell of the sea. Looking to buy. Thank you I knew we would need to supply the boat with doubles thank you for you story . Fair Winds

  11. I’m one of these foolish souls that you speak of, with a “dream” to sale around the world one day but no notion of how to make it a reality. This is the best article I have read on the subject since I got this hairbrained idea over a year ago. Despite the woes and warnings, I think this just makes me want to do it even more. I’ll be adding this blog to my regular reading for sure. Awesome article and great advice 🙂

  12. I enjoyed reading your article. It seemed to be an honest assessment of your life-experience sailing. My wife and I have toyed around the idea of a sailing adventure and appreciate the feeling of freedom and simplicity that sailing affords. We are in the dream stage of what such an adventure would be, and your article is an eye opening case for pause. My two cents… everything costs, a college education costs, early retirement costs, choosing a spouse costs, buying a sailboat is a money pit.
    Maybe, the pommegranate sunsets, morning coffee overlooking Mt. Belvedere at Cook Bay, just maybe the afternoon sail by Orcas Island, or the Tahitian boy giving you the finger as you wave to say hello are worth every miserable penny, colorful exploitive, and again, just maybe all of these simple experiences be worth more than any amount of money could possibly buy. The Dream lived, is better than not to have dreamed at all…

    • Thanks Rudolph, appreciate your comments. Seems like another world now, so many years ago. The business is still going strong but 13 straight years at sea for me was a time I will always be grateful for- so many amazing experiences! But it’s nice to be back in the mountains where I grew up and now only take limited trips to the boat. Much more manageable now! Good luck!

  13. I like that you suggest finding an appropriate boat for what you are wanting to do. My dad was really into sailing as a kid and wants to get into it again now that he has more time on his hands. I will send him this information so he can find a marine service to help him choose a boat.

  14. It’s good to learn that you should do a full tour of the safety systems when considering buying a sailboat. My wife and I are looking to buy a sailboat and we were wondering what we should look for in a good boat. I’ll be sure to tell my wife that we should get a sailboat that has all of its safety systems intact.

  15. That’s a good idea to make sure that you choose a bot that is made out of a material that you like. I feel like that would make it easier for you to determine factors like the weight, and how easy it would be to repair it. I’ll have to do some research into that if I get a boat since I would want to get one that would be easy to have fixed if I got a boat.

  16. Thanks for pointing out that you should take a sail with an experienced sailor before you buy a boat yourself. My wife and I are looking for hobbies to get into and sailing looks quite appealing to us. We’ll be sure to keep your tips in mind as we do more research!

  17. It’s great that you talked about equipping the boat for offshore use over the course of a year. My spouse and I are thinking about getting a new boat soon so that we can spend more time on the water. We need to learn how to care for the boat so that it stays in good shape for a long time.

  18. It’s good to learn that boats made from aluminum have to be welded correctly. My wife and I are wanting to get a boat for our family and we were wondering what we should look for in a good aluminum vessel. I’ll be sure to tell her that we should make sure the aluminum parts on the boat are welded together well before buying it.

  19. I never realized that there were so many different types of boat materials to choose from, like wood or steel. My partner and I are thinking about getting a boat later this year. We want to be able to take our family out on the water whenever we want.

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