Getting started with
retirement on a sailboat

Galleon Contact me.

Zaphod Beeblebrox: "There's a whole new life stretching out ahead of you".
Marvin: "Oh, not another one".
- Hitchhiker's Guide to the Galaxy

Site Map


My goals

  • Get out of "spending whole life in an office and an apartment" rut.
  • Have fun.
  • Explore world.
  • Get out of rat-race.
  • Learn new skills.
  • Meet people.
  • Live life a new way.
Pickles cartoon

"Twenty years from now you will be more disappointed with the things you didn't do than by the things you did ..."
- Mark Twain

"It is part of the nature of man to start with romance and build to a reality."
- Ray Bradbury

From Tony Bullard on the SailNet liveaboard-list:
Often a lot of people new to the idea of cruising ask questions that really boil down to what is the "right" way to cruise.

I think it is very important to understand there is no 'right' way, there are just lots of different ways. ... For each of us the right way will be different and change over time.

The really important thing is to get started, try some form of cruising that is right for the moment and go from there. I see and talk to so many people, now in their mid-70's, who kept waiting for the perfect right moment to go cruising. Guess what? They never made it before their health failed.

Sandy and I are just 9 weeks away from full-time cruising. It's incredible just how many things try to get in the way of our departure date. Our land friends, realizing we really are about to leave, are putting additional pressure on us to stay. Things KEEP BREAKING on the boat. But, except for a hurricane in the gulf we will depart over the Thanksgiving Weekend, even if we have to have someone tow us out into Tampa Bay.

Even if everything gets screwed up and we become destitute and homeless, at least we tried it. Much better than never trying at all.

Don't get too intimidated by the amount of information on this site and the number of things to know about cruising. You don't have to know it all right away, many people cruise successfully without knowing much of it, it will become clearer as you get your hands on the equipment, and there are books and fellow cruisers and boatyards to help with it.

Summarized from article by Tom Neale in 7/2004 issue of BoatU.S. magazine:
Tips for living aboard:
  • Live aboard for the right reasons. It won't be carefree. Cruising close to home can be more fun than long-distance cruising.

  • Be realistic. Don't feel you have to circumnavigate or go to the Tropics. Do what you can afford.

  • Be comfortable. No need to do without refrigeration and other comforts.

  • Extended cruising is different from weekend cruising. Extended cruising takes a different boat, more skills, different mindset.

  • You need a serious dinghy.

  • Having tools, spares and skills to fix things is critical: will make you safer, save money, give you freedom.

  • Weather skills are important.

  • Anchoring is a critical skill. Get good ground tackle.

  • Practice cruising near home before taking off on a big cruise.

  • Don't try to run on a schedule.

  • Figure out how to handle mail.

  • Figure out how to handle communications.

  • When you're ready, go. Don't wait for everything to be perfect; it never will be.

  • If you can't afford to retire, don't. There are lots of ways to cruise other than long-distance full-time.

Various types of boating

  • Day-sailing (go out for 4 or 8 hours of boating on a weekend day).
    Good: doesn't require fancy equipment; can take friends out often; can still live in nice house and have normal job.
    Bad: can't get to really interesting places.

  • Racing.
    Good: can hone skills; enjoy competition; enjoy teamwork.
    Bad: expensive; specialized; need to find races; probably need crew.

  • Living aboard (using the boat as a house, in a marina or at anchor).
    Good: can have normal job; doesn't require fancy equipment.
    Bad: can't go to really interesting places; engine may decay from disuse; some marinas are getting bought out by developers; may have bad neighbors.

  • Coastal cruising.
    Good: lots of interesting places to go in USA; still have access to nice facilities (stores, internet, medical, etc); close to safe harbors; not as much equipment needed as for longer-range cruising.
    Bad: can't go to really interesting foreign places; hard to have a steady, normal job.

  • Long-range cruising (for example, Caribbean).
    Good: could spend a lifetime seeing the Caribbean.
    Bad: need good boat and skills; need language skills and vaccinations; can't have any job because foreign countries won't give work permit; will be separated from friends and family; medium level of danger (from weather, accidents, crime, disease).

  • Ocean passagemaking.
    Good: can go anywhere in the world.
    Bad: need top-notch equipment and skills; highest levels of separation and danger.

You can start with one type of boating and migrate to others, as you work out your lifestyle. I started with coastal cruising, and after 3 years I started some long-range cruising.


My strategy

  1. Learn tons of stuff about boating (read, take classes, sail small boats).
  2. Quit job.
  3. Give up apartment.
  4. Go to Florida.
  5. Buy big sailboat.
  6. Live on it and sail forever (?).
I considered moving to Florida and getting an apartment and job there, while looking for a boat. But a casual search didn't show many good computer programming jobs in Florida.

My girlfriend wanted to find a waterfront house in Florida that had a sailboat-capable dock, so she could have a house and I could have a boat. Houses like that are very expensive. And we would have ended up with two big things to maintain.

As soon as you even start thinking about living on a boat, start simplifying your life

  • Sell house and get into an apartment.

  • Sell extra vehicles and equipment and furniture.

  • Reduce number of credit cards, bank accounts, etc. Reduce the number of bills you have to pay every month. Reduce the amount of paper mail you get; pay bills online.

  • Avoid accumulating new things, especially things that will be hard or costly to get rid of later (pets, new cars).

From Tom Gessler:
... No burning of bridges, because you will probably eventually return as all of us do. You must have something to come back to.

Don't buy a big boat before you're ready to live on it. Big boats take a lot of time and attention. You don't want to have the boat sitting decaying and running up bills in a marina or boatyard in Florida while you're back in Utah trying to sell a house or something.


"If everything's under control, you're going too slow."
- Mario Andretti

My plan (and I kept to it)

  • 1999 - 2000: Take classes, build up sailing experience, read books, do research, ask questions. My progress.

  • Start of 2001: Look for sailboat to buy in Florida. My progress.

  • 3/2001: Sell my junk, quit job, move from CA to FL, buy sailboat. My progress.

  • 2001: Coastal cruising and living aboard in Florida Keys. My progress.

  • 2002-2004: Cruising in Bahamas, Florida, Chesapeake, inland rivers. My progress.

  • 2005-2014: Cruising in Bahamas and then Caribbean. My progress.

  • 2015: I've had enough; I want to sell the boat.

  • 2015: Boat half-destroyed by hurricane Maria; sold the boat for a pittance.

S.V. Date's "An Atlantic Odyssey"

Very good book: "The Cruising Life" by Jim Trefethen.
Different types of cruisers, why people should/shouldn't cruise, what kind of boat to get, etc.

Book worth reading (just okay, not terrific): "Managing Your Escape" by Katy Burke.
Covers making the decision, career, budgets, kids, money, mail, insurance.
But a bit superficial and incomplete, and definitely a bit outdated.

From David Guenther on Cruising World message board:
Make sure you have a good sense of the reality before you do anything major. I had an acquaintance who had the dream. He spent three years building a boat from scratch. He was an engineer and had done a marvelous job. With one year left until completion, he figured it was time to try the cruising lifestyle -- and discovered he didn't like it. He never finished his boat; just sold it for what he could get.

On the other hand, selling everything and going is the ultimate commitment. You will give it your all because you have nothing to go back to. There is really no truer test.

What you will probably miss most are your friends, family, and other people in your life. But modern technology makes it easier to stay in touch and you will meet many new friends along the way.

Although some people maintain a house/condo to return to upon occasion, that didn't work for me. I had rented out my house and it was trashed by the tenants. I ended up worse off financially than if I had just sold it and the problems of dealing with it both distracted me and undermined my enjoyment of the cruise. Presumably, my experience was atypical. But, if you go this route, it highlights the need for a good rental agent/caretaker while you are away. And remember, if you keep a house/condo that is rented out, you will not be able to return to it any time you want. That means you may need to rent shore-based accommodations anyway, which is the same situation you would be in if you had sold your house.

Had I to do it over again (and I plan to), my current thinking is to sell everything but invest a portion of the proceeds. The principal amount will be a reserve which I can use to resume shore-based living when the cruise is over or for an extreme emergency while cruising. The income generated by the principal will add to the cruising kitty. The balance of the proceeds becomes the upper limit to the amount I will invest in a boat and equipment. If worst comes to worst, it is an amount I can afford to lose. And if I succumb to the desire for shore-based living while cruising, I will just rent someplace for a while in an interesting location I have never lived before, temporarily substituting one journey for another.

From Nancy Birnbaum on World-Cruising mailing list:
... Anyway, the thing that the guys didn't relate that I think is as important as the technical information, is the emotional aspect of preparation for cruising.

Before my mate and I left on our voyage, we took a very helpful course on compatibility, communication and relationship dynamics. Unfortunately, the course is only offered in Colorado right now, but you could probably find something similar in your area, or even a good relationship counselor. I'm talking "preventative relationship counseling" or call it - relationship prep!

The difference for most couple between their regular lives and their cruising lives is huge. It's way different being together 24/7 in a small space with little privacy and less timeouts. Even if you get along great, you'll benefit from taking some time to access your relationship and discuss "what ifs", "what do we do when," and "how should we handle ... ?"

The biggest surprise for me (and know that I have two degrees in Psychology and ran a counseling program!) was just how stressful it would get for my mate, and therefore, for me. The more stuff broke, (and things will always be breaking) the more stressed out he would get. Amazingly, he was able to fix just about everything that did break, but it all took it's toll. The more stress, the more arguments, lashing out, etc.

I found out from cruising couples that men often have a harder time adapting to cruising life if their job was how they identified themselves in their "life before cruising." They simply had no new "identity" and felt a bit lost. Of course most of them become diesel mechanics and boat technicians! But, I guess it was easier for me since I had interest in many things. I brought along my jewelry/bead-making supplies and either traded or sold or just played with other cruising women along the way. I kept a journal and created and maintained a web site of our voyage, shopped for interesting provisions, took lots of pictures and just enjoyed the sun, water and touring. We sharing most tasks except for the "blue jobs/pink jobs." He changed the oil, I cooked! We both navigated, prepared the boat for departures, ran and monitored all the systems. He anchored, I steered. We both docked, ferried fuel and water.

It's important to have some kind of hobby or craft or something for the long passages, rain days or to share with others.

Last, but not least ... The very best part about cruising for me (and my mate too) was the incredible fellow cruisers we met along the way. Some of the best folks you'd find anywhere. Be sure to create some "boat cards" (like business cards, but with your boat name, make and your info on it. Maybe a picture of the boat or you two as well!) to give out to folks.

From "The Cruising Life" by Jim Trefethen:
Don't buy the boat too early in the planning process. A boat is expensive to store, it depreciates, you lose the opportunity cost of the money, you have to maintain it even while not really using it much, you may buy the wrong thing before you know more.

Don't spend all your money on the boat. Some cautionary tales:
Jon Lockett's "Couple who sold everything to sail around the world lost it all when their boat SANK after two days at sea"

From /u/BMCBoid on reddit:
11 Things I wish I knew before I started Sailing:
  1. Learn on a dinghy - A dinghy will instantly punish you for any mistakes you make by capsizing. A keelboat will let things get a lot worse before you even know that there is a problem. The dinghy's are the hardest to sail and the most sensitive to trim. Learning on a tiny little boat is cheaper and it teaches you excellent sailing habits.

  2. Sailing is very expensive. - It seems that just writing the word Marine on something allows a marketer to triple the price. You can find suitable replacements that are not marketed as marine quality, but it is difficult.

  3. Finding good crew is very hard - Most sailboats take a couple of people to run. I got a boat so I could go boating as often as I like. One thing I didn't realize at the time is that if I wanted to go sailing every weekend, I should just go to the marina and ask people at the gate if they need crew for a day.

  4. Don't spend all your money on the "fun" stuff - I was thinking of refitting the interior on my boat but then the steering broke. That was really costly, so it's important to remember to have some money and time set aside to take care of the critical operational items.

  5. Don't give your crew a time that you will be back at the dock at the end of the day. Generally when we go out, it's to get away from it all. I generally try to tell people to set aside their day if they are coming out sailing, as working to a schedule when you don't need to isn't as fun.

  6. Bigger boats are easier to maintain - I had a 26' boat and every time I wanted to work on something, it was on my back, twisted up and in the dark. I now have a 35' boat and getting to everything is much easier. I can sit comfortably and work on nearly every system with excellent access.

  7. DIY is your friend - This is where the real savings of boat ownership comes in. If you can manage to take care of the basic maintenance and cleaning yourself, that is where the real cost of ownership comes down.

  8. If you don't have SCUBA gear, don't do your own bottom scrape - I tried this. After an hour of taking a breath, diving under, scraping a few feet and then coming up for air, I was totally exhausted and realized the $70 is so worth it for me to not have to do this every few months.

    [I disagree with this one. I am/was a full-time cruiser, and used snorkel gear to scrape the bottom of my 1973 Gulfstar 44 motor-sailer (44 feet long, 14 foot beam, acres of wetted surface). I had the time to do it, no hurry to do anything else. And doing it yourself keeps you in touch with what's going on below the waterline; is your zinc okay, your cutless bearing, your prop, your rudder, your hull, the through-hulls ? And it prepares you for when you are out cruising/sailing and get a line or net in the prop and have to snorkel down there to remove it; no SCUBA diver available then.]

  9. Lessons are worth their weight in gold - I did a ton of reading before I got really into sailing on keelboats. I knew a lot of the general principles as written but nothing can replace the value of an experienced and knowledgeable person showing you the ropes while out sailing with you. I highly recommend going through the ASA courses as a step one into sailing. You will be out on the water better prepared than most of the people out there.

  10. Expect things to go wrong and Don't Panic - I once heard a saying that said something along the lines of "the true measure of the skill of a sailor is the sum of the mistakes he has recovered from". I have had a few equipment mishaps and thankfully nobody hurt. I think the best advice is to keep a cool head whenever something breaks and understand that you are going to be OK. Try to find a creative solution to fix things.

  11. If you can dock or anchor before solving a problem, do that - If you can safely do it, get the boat to a steady state where you don't need to mix operation and repairs. There is so much less stress involved if you know you and your boat are secured before you start worrying about how to fix an equipment problem.

How to cut ties with land

  • Start early (right away); everything takes longer than you'd think.

  • Simplify your life; get rid of furniture/house/possessions.
    Don't put stuff in storage: it's expensive, stuff rots or gets stolen, they'll sell it if you're late paying a bill, and you'll just throw it away later after paying to store it for years.
    From Mary Heckrotte on The Live-Aboard List:
    ... you could rent a storage unit as we did. Now, of course, after 11 years cruising, we wonder what's in that storage unit, what could possibly be worth the $60/month we pay (that's $7,920 if anyone is counting!!) And on top of that, we never have enough time when we are Stateside to sort through the stuff, so we just keep sending in $60 a month for unknown junk that's probably all rotten. Go figure! It's just madness. Better to get rid of it before you're stuck with it!

  • Have a plan and goals, but accept that there will be adjustments and changes.

  • Enjoy the learning and the process; don't expect everything to change from not-fun to fun on some magic date.

From article by Webb Chiles in 10/2006 issue of Cruising World magazine:
  1. Find a place where you can live aboard a boat.

  2. Get a boat.
    There is no magic answer to what to get, but used, fiberglass and 36-37 feet is a nice choice.

  3. Move aboard.
    Probably cheaper than paying rent ashore, and eases the transition when you finally do sail away. And you'll know the boat better. But living aboard while working ashore has its own challenges.

  4. Sail the boat and get yourself in shape.
    Generally overlooked by those planning to go cruising; they work on their boats and buy equipment, but don't sail them enough.

  5. Set a precise departure date.
    When the day arrives, don't put it off because there are a few more things to fix on the boat; there always will be a few more things to fix. Unless the weather is horrible or something major is broken, stick to your date.

  6. Go.

From Gary Zuehlke on the SailNet liveaboard-list:
I wondered how people managed to live aboard myself. When I asked people I got one of two answers, either have lots of money, or lots of sacrifice. ... I figured I would have to go the sacrifice route. The amazing thing I learned really fast: they are really good sacrifices. The one I realized the quickest, it is cheaper to do your own boatwork, rather than have someone else do it. Some would call this a sacrifice, I chalk it up to learning how to do new things. ...
Other "sacrifices": living with fewer possessions, consuming less, being more self-sufficient, being more flexible (weather, breakdowns, etc), being more exposed to weather/nature, living a less conventional life.

Possible Problems / Issues / Challenges

Boredom and loneliness

  • Get partner.
  • Visitors.
  • Connectivity (radio, TV, phone, Internet).
  • Travel.
  • Keep learning (books, hobbies, languages, boat stuff, nature, musical instrument).
  • New sports (kayaking, snorkeling, fishing).
  • Charter out boat ? (probably not)
  • Co-own ? (probably not)

Run out of money

See my Costs Of Buying And Cruising On A Boat page for details.


Boat too big for one person to handle

  • Get partner.
  • Get crew for difficult passages (see my Crew and Guests on a Boat page).
  • Modify boat (auto-pilot, power winches, roller-furling sails, etc).


  • Insurance.
  • Medical training.
  • Proper medications on board.
  • Medical checkups, vaccinations.
  • Stop smoking, eat healthily, exercise.

Danger (sailing)

Ship sinking in storm  Solutions:
  • Sailing school.
    I took small-boat courses to get ASA certified, and then got a one-year membership and sailed their boats about every other weekend. Great experience.
    I considered taking a 7- or 10-day big-boat intensive class. I think the small-boat classes worked out better. For the same money, I got a whole summer of classes, plus the one-year membership. About the only thing the intensive big-boat class would have added is exposure to what it feels like to live aboard for 7 or 10 days (which is valuable). Everything else you can learn on small boats or pick up once you have your own big boat.
  • Safe boat.
  • Safety equipment (for lightning, fire, flooding).
  • Safe itinerary.
  • Get experience before going on own.
  • Get experienced crew.
  • Never stop reading, thinking, evaluating your own performance.

From Bill Rane, quoted on the WorldCruising mailing list, in response to someone's message about "world cruising and circumnavigating":
Yes, I have more open-ocean/blue water sailing experience than anyone I know, and I consider myself the consummate world cruiser. But I must confess something to all of you ... and please take me seriously ... I would never, never, never consider going world cruising or undertake a circumnavigation with a just a "couple of years" experience. That goes for even if I were sailing in a full-time job getting that experience.

I am well aware that you are all adults and can do whatever you want ... and that you probably will, but if your experience level is as you describe it, I think you are thinking very dangerously. World cruising is not a cakewalk ... it is not even easy. It is very, very dangerous, and the only thing that makes it even remotely enjoyable is sailing with people who know what they are doing ... who give you a degree of comfort that if anything happens that you cannot handle, someone on board can ...

I think dreams are wonderful ... everyone knows I have them myself, but I am quite proud of the fact that after over 70 ocean crossings of varying lengths, and four near-circumnavigations, I am still alive to tell about it.

I am not trying to brag, but if you want to have a "come to Jesus" session on this medium, tell me, and I will participate. I will tell you stories, all true, about 80-foot waves hitting you head on the bow; I'll tell you about being lost at sea with no navigation equipment and clouds so thick you could not see stars if you wanted. I will tell you about being shot at while some modern-day psycho gets his jollies at trying to steal your boat.

If I sound like I am over-reacting, maybe I am ... but I have found two boats in my life ... in mid-ocean ... with no crews ... each one a trip started by novices.

And if you do decide to go, God be with you and be careful. I just ask that you re-think your ideas ... maybe modify them a little. Go with some experienced people first.

From Latitude 38: for every boat that sinks underway, four go down at the dock.
From McRory's Logbook:
Sailboat sunk at dock

One serious hazard: containers lost from freighters

But from Dave White on the SailNet liveaboard-list:
I have been sailing for over 30 years. The last fifteen have been both across the Atlantic and Pacific. For pleasure and deliveries. I can without question say I have never seen a container, let alone bumped into one.

Cruising/sailing is less dangerous than driving a car.

From John Cikoski on CompuServe's Sailing Forum:
... Sailing is the easy part, the pleasant part, and -- get this! -- the SAFE part. Take it from one who's been doing it more than thirty years, the safest thing you can do in a boat is sail it far from land.

Is there anything dangerous about living aboard in harbor while learning to sail? Let me add a few words to your vocabulary: Anchor. Set. Rode. Chain. Rope. Scope. Tide. Swinging. Dragging. Bowsprit. Fending off. Coral head. Pounding. Hull breach. Grounding. Surf.

And these words: Through-hull. Electrolysis. Corrosion. Leaking. Cabin sole. Bilge pump failure. Groping in bilge in darkness. Desperately pumping up dinghy.

And here's a word you probably already know: hurricane. Have you ever experienced wind over 100 MPH? There is simply no way to imagine it, so you're probably right to refuse to think about it. ...

aground1, aground2

I suspect that sailing singlehanded (especially the danger of it) is the biggest problem I'm facing. I wouldn't do it if I didn't have to. See my Sailing a Boat SingleHanded page.

From John Rousmaniere, in Cruising World's "Safety At Sea":
Formula for Disaster:
  1. Rushed, ill-considered departure.
  2. Potentially dangerous route.
  3. Lack of alternative on route.
  4. Unprepared or small or inexperienced crew.
  5. Unprepared boat.
  6. Crew panic after injury.
  7. Weak leadership.

From "Safety Offshore" article by Thomas and Vicky Jackson in 11/2000 issue of Sail magazine:
Factors in Human Error:
  • Poor information (weather, navigation): must do basics right, track location and hazards.
  • Fatigue: must pay attention to crew state, sleep/wake cycles.
  • Inertia: changing conditions require decisions/adjustments.
  • Panic: must practice/rehearse/think about emergency scenarios.

Typical sailing mistakes most beginners make (I've done the first 8 so far):
  1. Loose dockline or spinnaker sheet gets into propeller.

  2. Run aground because I didn't stop sailing when fog closed in really tight.

  3. Run aground because I assumed my helmsperson knew to tack to stay in channel.

  4. Left dock with lunch still in the car instead of in the boat.

  5. Let boat get overpowered (fail to reef).

  6. Assume the skipper knows what he's doing.

  7. Fail to listen to the little voice in the back of your head saying "this is risky; it is too rough today".

  8. Keeping sail up through a squall or front, until it gets strong enough to damage or destroy the sail.

  9. Not keeping BOTH ends of all halyards secured at all times.

  10. Not attaching bitter end of anchor rode to boat.

  11. Not lined up properly (cut corner) to enter a small pass; ground on shoal at mouth of pass.

  12. "Short tacking" when going to weather; sometimes covering more distance is faster and easier.

  13. Inattentive to details (see red marker in expected place, but not check for correct number).

  14. Fail to notice or react to first sign of being off-course.

  15. Do things the hard way / ignore clues (observe other traffic, features on shore, etc).

  16. Steering by looking ahead only; current/wind may push you out of channel even though you're still pointed at destination.

From Dennis Fria of Mustang Island Yachts:
... I generally have just one smart bit of advice to the folks that I've helped on their way: Crawl, before you Walk, before you Run! Those people who start off with the hard stuff first seldom get very far! Too frequently I see new cruisers here who want to prove something (usually to themselves) and do so by setting out [from Texas] straight across the Gulf of Mexico headed to Florida. And with little or no experience! And all too frequently in the winter! Now that's just plain insane! And typically those people quit after they get to Florida! Or get a divorce! ...

From James Baumgart on World-Cruising mailing list:
I think a useful exercise would be to produce a list of real threats that blue water cruising crews face. Then get prepared to deal with those threats. In my opinion, there are ways to minimize each danger. Also, in my opinion, I've listed the most serious REALISTIC risks facing a cruising boat. We've had all of these situations on our cruise.

(1) Grounding. Go slow, have primary and backup depth sounders, avoid transiting coral shallows when water colors are not visible. Have adequate gear for kedging off. Have at least 3/4 keel boat with skeg-hung rudder and protected prop to minimize possible grounding damage. Steel boat is nice. Don't panic. We grounded about 5 times on the year-long voyage, and towed 2 boats off sandbars along the way. Never any damage - even with exposed props/rudders.

(2) Engine stops. Line around prop - make sure you are never dragging any of your own lines, watch for crab pots, filter your fuel, use biocide, change oil, change zincs, do an engine inspection daily (and hourly while underway). Don't shut down a running diesel in a crisis or near crisis. Install alarms. Always have mainsail ready to hoist. Always have anchor ready to drop. A bilge pump alarm saved us when an engine cooling hose blew, resulting in a minor $7 repair instead of an emergency rescue.

(3) Anchor dragging. Have oversized anchor and chain, use proper scope, set two anchors when concerned about holding, always back down properly, carry CQR/Bruce and Danforth (for different bottoms) plus a backup anchor, never leave boat until at least 30 minutes of close observation, return if there is a significant wind shift, carry a handheld VHF when away monitoring 16. We also carried 250 feet of line for making boat fast to the shore if necessary (and used it several times).

(4) Bad weather. Have SSB weather radio or weatherfax, use daily. Have everything secure on deck at all times. If coastal cruising there is no excuse to be caught out in bad weather - wait for good weather, be prepared to turn back or seek alternate harbors. If blue water cruising, have strong boat with positive righting moment capable of withstanding knockdowns. Smaller lexan windows, bombproof hatches, oversized rigging, storm sails, small cockpit, large drains, sufficient pumps. Get crew experienced gradually in heavy weather sailing. Reef early. Be sure to know how to heave to, lie ahull, or stream warps, at the appropriate times. Radar, GPS chartplotter are technical aids, but good seamanship comes first. Carry a knife, axe and bolt cutters capable of cutting your anchor chain.

(5) Injury. It's easy to get cut, sick, bruised, or broken. Carry adequate first aid and medical supplies. Marine SSB or Ham radio can work wonders if a serious medical situation happens far from help. See your doctor before the trip and prepare a medical kit.

(6) Getting Lost. Even in the world of GPS it's easy to do. Have adequate paper charts, acquire local knowledge. Don't overly depend on cruising guides at the expense of your better judgement. Double-check waypoints, it's easy to transpose digits, North versus South, 45 degrees 11 minutes instead of 46 degrees 11 minutes (I've done both). Getting lost will translate into threat (1) or (7).

(7) Hitting something. Usually while docking, locking, or going under a bridge. It never happened to us but to several of our buddy boats. Not much you can do. Bow and stern thrusters would be nice (but unaffordable). Learn to use spring lines for maneuvering. Practice, practice, go slow. Even then a cross current will do you in sometime. Have liability insurance. Have an old boat that can stand a few dings and you can repair yourself. Never insist on right-of-way. Be able to repair your longest piece of standing rigging.

(8) Seasick. Not much you can do. It usually goes away after about 3 days at sea. If it doesn't, look into medications or sell the boat. The transderm patches work but cause hallucinations after a while.

The rest never happened to us.

(9) Bad People. Travel in a group. Avoid dangerous places. Keep the VHF on 16 at all times. Having a fast boat is a good thing. We never locked the door in 12 months and 5000 miles (except in New York City).

(10) Leaks. Carry underwater sealant, plenty of 5200, wet suit, mask. Don't leave in the first place if your boat has serious leaks (ex. deck/hull joint). Know how to adjust your stuffing boxes. Have softwood plugs for the through hulls, and exercise the valves regularly. Call for help in a bad situation. Even in a remote anchorage, people will respond. We knew of a boat that hit rock or coral, had 3 feet of water in the bilge and more on the way, generator under water, battery and pumps out. Local people responded to their handheld VHF call for help, directed them to a place to beach the boat, and brought portable pumps out, patched the hull with underwater epoxy, towed them off, and sent them on their way to the nearest boatyard. If this happened mid-ocean it would have been time to call Mayday on the SSB/HAM, trigger the EPIRB, and step up into the lifeboat.

(11) Crewperson is hating it. Change what you are doing.

From "25 Dumb Things To Do on a Sailboat" in 11/2006 issue of Sail magazine:
  • Sail into a harbor with the spinnaker up (looks really cool, unless you can't get it down).

  • Get the dinghy painter wrapped around the prop.

  • Dip a bucket overboard at 7 knots.

  • Release a rope clutch without first taking turns around a winch.

  • Walk along the leeward side of a (heeling) boat.

  • Make a flying leap onto a dock.

  • Leave the handle in the winch.

  • Fend off another boat with your hands or your feet.

  • Start an outboard while it's still attached to your stern rail.

  • Believe that power always gives way to sail.

  • Sail between a barge and its tow.

  • Let go of the mooring before the skipper tells you to.

  • Leave the forehatch open while you're working on the foredeck.

  • Think that just one more stroke of the pump will unblock that toilet.

  • Leave harbor with the sailcover on and the anchor stowed.

  • Straddle a line leading to a highly loaded block.

  • Anchor without first checking the chart.

  • Forget to secure the bitter end of the anchor rode.

  • Tow a dinghy in a big following sea.

  • Go sailing without checking the weather forecast.

  • Sail dead-downwind without rigging a jibe-preventer.

  • Go coastal cruising without paper charts.

  • Forget to open the cooling-water seacock before starting the engine.

  • Pick up a mooring under mainsail when the wind and current are opposing each other.

  • Get the deck fillers confused.

Danger (crime)

  • Low danger if take simple precautions like locking the boat up, avoiding some areas of the world. And there is more violent crime in the USA than most other places in the world.
    Bluewater's Newsletter #4 - Piracy
  • Alarm system. (I use an $18 motion-detector from Home Depot in my cockpit.)
  • Locking grates on hatches.
  • Some kind of lock-box built into boat.
  • Insurance (probably not obtainable, except for theft of entire boat).
  • Travel with other cruising boats.

From John Dunsmoor:
Never forget in a lot of cruising venues you are the rich AMERICAN sailor and the cost of the windlass is an annual salary for many you come into contact with. There can be an overwhelming amount of pressure to move some of your obvious riches from your pockets to theirs. This can be in the form of offering you items for sale, trade, theft, scams, solicitation for bribes, fees for everything from guides to security for your vessel.

I one time had a Bahamian offer me fresh lobster for a dollar a piece, out of season. I rejected the offer being somewhat suspicious and heard later that some sailor had his vessel confiscated and was deported back to the states for violating Bahamian fishing regulations. Some three weeks and thousands of dollars in legal fees and fines and they were back on their vessel. I also heard that the informant was paid a "reward" for turning in this scofflaw. Five minutes of stupidity resulted in a ruined cruising season.

Another couple took a "job" doing some remodeling and painting for a home owner on one of the islands. A local "informed" the authorities that these non-resident, without working permits, aliens were working and being paid. The authorities showed up at the residence and arrested the couple, give them the choice of being put into a Bahamian jail or being deported. The couple arrived in Fort Lauderdale with no more than the clothes they were wearing and their vessel was sitting un-locked in the anchorage. Fortunately they had friends both here and there and a couple of sailors actually sailed their boat to Fort Lauderdale. Their ordeal only cost them five hundred bucks for air tickets.

Sailor beware.

From another person: In some countries (such as the Dominican Republic), your US passport is worth its weight in gold to a thief. A stolen US passport is an instant ticket into the USA for someone.

Discover I don't like the lifestyle

(Feel shackled to boat, too much maintenance, too isolated, monotonous)

  • Test cruise (before buying): too expensive, not realistic.
  • Volunteer as crew for a while (before buying).
  • Read a lot about other people's experiences (before buying).
  • Charter boat out occasionally (probably not).
  • Co-own so share boat time (probably not).
  • Spend money for on-shore vacations near the boat.
  • Spend money for vacations elsewhere around the world.
  • Adjust your lifestyle (change to coastal cruising, marina living, etc).
  • Move boat to a different area.
  • Get better communications (cell-phone, internet, satellite TV).
  • Spend money to have someone else do the boat-maintenance.

See my Lifestyle of Living on a Boat page for more details.

No: newspapers, restaurants, videos, library, TV, radio

  • Visit port.
  • Library at home port.
  • Satellite TV ?
  • Internet.
  • Some interesting content is broadcast on shortwave radio.
  • When coastal cruising or in marina, all of those media are available.

Lack of exercise

(I like to hike and play tennis.)

  • Swim.
  • Kayak.
  • Hike in port.
  • Row dinghy.
  • Climb the mast every day (not !).
  • Constant motion of the boat gives you a workout of sorts.

Stress during the land-to-boat transition

Stress comes from:
  • Change of place.
  • Fewer comforts and possessions.
  • Pressure of learning boat operation, maintenance, repair.
  • Less contact with family and friends.
  • Loss of familiar routines (work, house, etc).
  • Fear of failure, mistakes, financial loss, unhappiness.
  • Worry about spending all that money (for boat, repairs, equipment, moving, etc).
  • Keep contact with family and friends (phone, email, visits).
  • Meet other boating people; get their help and advice and company.
  • Minimize the number of changes; take them one at a time.
  • Spend time away from the boat, doing other things.
From "Gently With The Tides" edited by Michael Frankel:
Moving aboard is a big step for most. Cutting the ties with a land-based home is often a traumatic and fearful experience at first ...

Boat type doesn't seem to matter much in the decision to move aboard or in the angst one goes through before the transition is complete. ...

To Research

Classes, lessons, schools, seminars

  • Sailing lessons:
    Start these ASAP and then get a club membership and sail as often as possible, in various boats and conditions and crews.

    I chose Spinnaker Sailing in Redwood City CA because it was closest to where I live. Especially because I wanted to get a membership and sail a lot after I took classes, and if you have to drive 90 minutes to get to the marina, you won't sail very often. I didn't look at other schools very much.

    Check out class offerings (which ones and how often), prices, facilities (marina, types and numbers of boats), sailing location, and get some sense of how tough it will be to reserve a boat when you're a member.

  • Boat-buying:
    • Chuck Gustafson's sailboat-buying seminar, Seattle WA, 2 days. Once a year, in the fall.
    • Jill Baty's sailboat-buying seminar. Oakland CA, 1 day. Once a year, in the spring ?

  • Boat-maintenance:
    Haven't found any ! Hard to believe.

  • Engine maintenance / mechanics:
    • Start by reading How Stuff Works's "Engines and Motors!".
    • At List Marine in Sausalito CA, there is a one-day class by Technical Education Institute (415-332-7544) that looks really good.
    • Demystifying the Diesel Engine, one-day class at Windward Sailing Solutions in Redwood City CA.
    • Through National Women's Sailing Association: Diesel Engine Workshop, Mack Boring's Engine City Technical Institute, Union NJ. Two days.
    • Same or similar Diesel classes at Lincoln.
    • "Tradewinds Sailing Club in Point Richmond has just started offering a basic diesel class."
    • Several people have advised hiring a mechanic to come aboard and instruct me on my engine, instead of taking a class. Or pay a knowledgeable cruiser with same kind of engine to come aboard and teach you.

  • First aid:
    • Red Cross CPR/first-aid class, focuses on getting breathing/heart restarted and then calling 911.
    • Red Cross Wilderness Advanced First Aid class (not a standard class, not offered at all chapters), which is 3 days. But it has a prerequisite:
    • Red Cross Emergency Response Training class, which is 53 hours (12 four-hour evenings and 1 Saturday).

  • Refrigeration ?

  • Radio:

  • Celestial navigation:

  • Sail-repair:
    • At Hogin Sails in Alameda CA:
      The Basic Sail Repair class is a general overview of sail repairs and simple covers. We have a discussion and slide show in the morning and in the afternoon we do hands on work with people using our sewing machines to practice simple techniques.
      I took the class; it was pretty good. Lots of hands-on.

  • Sail-making:

  • Things best learned at sea ?
    • Celestial navigation.
    • Weather. (But SSCA sponsors Marine Weather Workshops all over the country.)
    • Marlinspike.
    • Stars.
    • Fish identification.
    • Languages.

  • Cruising/Passagemaking:
    • Cruising Symposium, 2 days (in Seattle, San Francisco, or Annapolis). Wonderful people: John and Amanda Neal (have been cruising for 20 years), Robert Perry (sailboat designer), Carol Hasse (sailmaker), Earl Seager (marine weather), George Day (editor of Bluewater Sailing magazine), Marilee Shaffer (radio/computer). Great info, but they really went through each topic very quickly. 200-page book that covers lots of subjects.
    • Tom and Mel Neale's cruising seminar, 1 day. Wonderful people, pretty good info. Major topics: legalities, tools, diesel tips, medical, anchoring, reading water depth.
    • West Marine Offshore Sailing Symposium.

  • SCUBA:
    From Dave Richardson:
    Some advice from a long term cruiser: take a real multi-day SCUBA course. I have been a NAUI diver since 1966 and my wife since the early '80s. You have no idea how often you will need it and even more often use it as a very pleasurable pastime as a live aboard cruiser. The first time you have to retrieve your 85 lb. Bruce and 300 feet of half-inch chain you have paid for the course and all your gear (excluding compressor). Scrubbing the bottom, removing a line from the prop shaft, cleaning the log paddlewheel, finding your glasses, or inspecting the chunk you just took out of the keel while entering a harbour that was unmarked are all easily accomplished with a minimum of gear. Then there is the unmatched beauty of a coral reef at 10 meters. Sheer ecstasy.
    So You Wanna Become a SCUBA Diver ?
    My thoughts:
    Before starting SCUBA class: practice lap-swimming in a pool, buy dive-quality mask and snorkel and fins at a dive shop, and practice using the equipment.

    I got SCUBA-certified, then never bought any equipment and never did any diving. BUT: the SCUBA class hugely improved my snorkeling skills, and I use them fairly often for boat maintenance as well as pleasure. So it was worth it.

    My check-out dives were kelp dives in Monterey Bay CA. Cold water, but great place ! If you live in a harsh and uninteresting place for diving, wait until you get to warm and interesting waters on your boat before getting certified.
    See my SCUBA Diving page.

  • Various:

Books    Book with pages flipping

Start by going to libraries and taking out every interesting-looking book about boats, diesel engines, cruising.

Then buy books, maybe through PriceSCAN.

Books I've read and recommend are listed under the appropriate sections on this site.


Forums / bulletin boards / Facebook Groups


Useful large web-sites

Boat shows

NCMA Power and Sail Boat Show, Oakland CA (fair number of sailboats, mostly Beneteaus and Catalinas; some used)
NMMA Boat Tour
Annapolis Boat Shows (October) (from Michael Rich on The Live-Aboard List: "It is a show for folks with $300k in their wallets to look at Shannons, Swans and the like")
Atlantic City NJ (January)
Newport RI (September)
St Petersburg FL (November)
From Joe Murray on the IRBS live-aboard mailing list:
Fort Lauderdale's show is geared toward power boats primarily. St Petersburg has a sailboat show in the fall, I believe. The Miami International Boat Show in February is the show with the greatest number of sailboats by far.

From Norm on the IRBS live-aboard mailing list:
Learn everything you can about electrical systems [and] fuel systems. After living aboard since 1981 and about 4,500 miles I have found these two systems have demanded most of my engineering attention.