Or: Why You Need to Untie Those Damn Dock Lines
One of the biggest questions facing anyone who dreams of going cruising is a simple one: When the hell do you leave?
I’ve spent years talking to people about cruising, standing in front of seminar audiences, giving lectures, and trying to convince folks that the best way to see the world is from the deck of a boat. I usually start by asking everyone in the room to raise their hands if they plan on going cruising someday. Like clockwork, 80 to 90 percent of the hands shoot into the air. Hell, that’s why they’re there. They’ve been dreaming about sailing away to exotic places, dropping the hook in some turquoise lagoon, and spending their days swimming, snorkeling, fishing, and generally living a life that makes their old neighbors back home wonder what the hell they’re doing wrong.
Then I ask a second question: “How many of you have actually set a date to leave?”
That’s when the room gets real quiet, and the hands come down faster than a drunken sailor falling off a barstool. Out of all those people who raised their hands a minute earlier, I’ll usually get two or three who have actually committed to a departure date. Those are the people who are going cruising. The rest? Well, they’re still dreaming about it.
And there’s nothing wrong with dreaming. Hell, dreams are what get most of us started in the first place. We imagine ourselves sitting on the aft deck of our boat, cold drink in hand, watching the sun set over Tahiti, Tortola, or some little island whose name we can’t pronounce but whose beaches look damn good in the travel brochures. We picture warm breezes, clear water, palm trees, and absolutely no reason to be anywhere at any particular time. It’s a wonderful dream, and it probably helps a lot of people sleep at night.
But somewhere between that sunset in Tahiti and the cold beer in the cockpit, reality sneaks into the picture. That little voice inside our heads starts asking questions. What about the boat? Is the engine reliable? Are the sails in good shape? What about the electronics? Have we got enough spare parts? What if the watermaker quits, the refrigerator dies, or we hit bad weather? What if we get all the way out there and discover we forgot something important?
Before long, that beautiful tropical dream has turned into a nightmare involving spreadsheets, credit cards, boatyards, and a project list long enough to make a NASA engineer reach for a bottle of whiskey. Some people decide they aren’t leaving until the boat is completely finished. Every system must be perfect, every electronic gadget updated, every locker stocked, and every possible spare part tucked neatly away in its proper place. These people, my friends, are in serious danger of never leaving.
Here’s a little secret about boats that the marine industry would probably prefer you didn’t know: Boats are never finished. Never. Ever. If you wait until everything on your boat is perfect, you might as well install a mailbox on the dock and have your mail forwarded there permanently.
There are three words you will almost never hear in a marina, anywhere in the world: “The boat’s finished!” You might hear someone say it, and you might even hear them say it with a straight face. But take a good look at their boat, and I guarantee you’ll find something they want to fix, replace, improve, upgrade, modify, or spend a small fortune on. There’s always another project waiting around the corner.
You get the engine running perfectly, and suddenly you decide you need a new alternator. You install the alternator, and now the battery monitor isn’t compatible. You replace the battery monitor, and somebody tells you that your batteries are old technology. Before you know it, you’ve spent six months rebuilding the electrical system when all you originally wanted was to go sailing. And that’s just one system!
Then there’s the financial planning, the insurance, the provisioning, the spare parts, the navigation equipment, the communications gear, the medical kit, and the paperwork. Add the kids, the parents, the job, the house, and all the other responsibilities that seem to multiply every time you cross something off the list. And don’t forget the latest wonderful invention that some salesman assures you will make cruising easier, safer, faster, or more comfortable. You absolutely must have it, he tells you.
Funny thing is, thousands of cruisers managed to cross oceans before that particular miracle of modern technology was invented. But now that it exists, you’re supposed to believe you can’t possibly leave without it. Pretty soon, you’re spending more time preparing to go cruising than you would spend actually cruising, and the years just keep slipping by.
The solution is surprisingly simple: SET A DATE.
That’s it. Pick a date, write it on the calendar, and make it real. It doesn’t have to be next month or even next year. Hell, if you need another year to get your finances in order, prepare the boat, or take care of important family matters, then set a date a year from now. Just make sure you set one.
Once you have a departure date, everything changes. Suddenly, those endless projects have deadlines, and decisions become easier. You start figuring out what you really need instead of obsessing over everything you might possibly want. You begin separating the essential from the merely convenient, and the merely convenient from the expensive toys you’ve convinced yourself you can’t live without. Most importantly, you finally have something definite to work toward.
Without a date, there’s always tomorrow, next season, or one more project to finish before you can leave. With a date, tomorrow becomes part of a plan. But there’s one more little detail you need to understand. When that date arrives, assuming you’re properly prepared and conditions are safe, YOU LEAVE.
You don’t move it simply because the boat isn’t perfect. You don’t postpone it because you haven’t installed the latest electronic gadget or cancel the whole adventure because a few items on your provisioning list are still sitting on the shelves at the marine store. You cast off, because if you don’t, that departure date becomes just another date you didn’t leave. Pretty soon, you’ll be right back to dreaming about someday.
Will everything be ready when you go? Of course not. You’ll forget something. Everybody does. You could spend a lifetime provisioning a boat and still discover, three days offshore, that you somehow forgot the one little part you need to fix something important. And spare parts? Well, there’s a universal law of cruising that seems to hold true regardless of where you sail: If you have a spare part, the original part won’t break. If the original part breaks, you won’t have the spare. It’s a law of nature, right up there with gravity and the tendency of boat projects to cost twice what you expected.
But here’s the beauty of it. Leaving the dock doesn’t mean you’re signing a contract to spend the next five years at sea without ever seeing another human being or a hardware store. It simply means you’re cruising. Need something? Pull into the next harbor. Forgot something? Find a store, borrow it from another cruiser, or figure out how to do without it. Something breaks? Welcome to the adventure.
You’ll learn to repair things you never imagined you could repair. You’ll discover that a little ingenuity, some basic tools, and a willingness to experiment can accomplish amazing things. You may even become a world-class expert in the fine art of Mickey Mousing a repair well enough to get the boat back into port. And when you finally get there, you’ll be amazed at how satisfying it feels.
There’s something special about fixing a problem at sea, especially when you’re a long way from home and nobody is coming to rescue you with a toolbox and a credit card machine. You learn to think differently, to improvise, and to make do with whatever you have on hand. You also learn that the difference between a disaster and a good sea story is often nothing more than a little patience and a roll of duct tape.
Then there’s the weather. Ah, yes, the weather. The great equalizer of cruising, and the reason every sailor develops a healthy respect for the ocean. Eventually, you’ll encounter rough seas, unexpected winds, or conditions that make you wonder whether taking up golf might have been a better idea. The first time you get caught in a real blow, you’ll probably be scared. That’s normal. The ocean is powerful, and pretending otherwise is a fine way to end up in trouble.
But every time you experience challenging conditions, you learn something. You learn how your boat behaves, what you can handle, and what you need to do differently next time. You learn to reef earlier, secure things properly, pay attention to the forecast, and stop believing that the weather cares one damn bit about your schedule. You also discover that a well-found boat is capable of handling far more than you might have imagined, provided you use good judgment and don’t ask it to do something beyond its limits.
And somewhere along the way, you discover something else. You’re capable of handling far more than you thought, too. That little knot that used to form in your stomach every time you imagined what might happen out there begins to loosen. The unknown becomes familiar. The fear doesn’t necessarily disappear forever, but it stops controlling your life.
You start to understand that cruising isn’t one enormous, terrifying journey across an endless ocean. It’s a series of daysails, taken one day at a time. You sail to the next anchorage, then the next island, then the next harbor. Sometimes you travel hundreds of miles, and sometimes you move only a few. Sometimes you sit at anchor for a week because the weather is lousy or because you’ve found a place so beautiful that leaving seems downright stupid. And sometimes you have to fix something, wait for a part, or change your plans entirely.
That’s cruising. You don’t have to conquer the Pacific in one giant leap. You just have to get out there and begin learning how to live your life afloat.
I learned a lot about that on a passage I once made from the West Coast toward Hawaii. We had set a departure date months in advance and arranged for a couple to fly in from the Midwest to join us. Another crew member had moved aboard a day or two early to help get everything ready. We had a schedule, a plan, a crew, and a boat that was as ready as we could make her.
Then, the night before departure, a storm rolled in. Naturally.
We held our going-away party aboard a rain-soaked boat, with the weather doing its best to convince everyone that leaving was a spectacularly bad idea. The wind was blowing, the rain was coming down, and small-craft warnings were flying. It was hardly the postcard departure everyone had imagined. But we had a date, and at five o’clock the next morning, we cast off and headed out.
The first three days were miserable. We fought heavy headwinds and steep seas, and the boat took a beating. So did the crew. Our guests from the Midwest began questioning my sanity, and they weren’t shy about it. They wanted to know why the hell we hadn’t waited for better weather. After all, we were headed across the Pacific. Surely there was no reason to leave in a storm when we could wait a few days for conditions to improve.
Their question was perfectly reasonable. My answer, however, wasn’t necessarily what they wanted to hear. By that point, I’d sailed across the Pacific five or six times, and in all those crossings, I’d never had a perfect passage. There was always some lousy weather somewhere along the way. Sooner or later, we’d encounter wind, seas, or conditions that made life uncomfortable.
I explained my philosophy to the crew. “If we leave in bad weather, it can only get better. If we leave in good weather, it can only get worse!”
They weren’t particularly impressed. For the first three days, they looked at me as though I’d finally lost whatever was left of my mind. Every time the boat slammed into another wave, I suspect they were mentally calculating how much it would cost to fly home. But we kept going, and eventually, as the weather began to settle, we spotted Guadalupe Island, roughly 150 miles off the coast of Baja California. We headed in and made a stop.
The storm passed, the sun came out, and the seas calmed down. The boat settled into a much more comfortable rhythm, and something else happened. The crew changed. Those first few days had taught them what a boat could take. More importantly, they’d learned what they could take. They had experienced uncomfortable conditions, watched the boat work her way through them, and discovered that they weren’t nearly as helpless as they’d imagined.
They had crossed a little bridge in their minds. The Pacific was still out there, stretching toward Hawaii, and we still had a long passage ahead of us. There would be more weather, more challenges, and undoubtedly more things to fix. But now they had something they hadn’t possessed when we left the dock: experience.
They had a better understanding of the boat, a better understanding of themselves, and a little more confidence in their ability to deal with whatever came next. That confidence was worth far more than another week spent waiting for the perfect weather window.
And that’s the point. You can’t learn to cruise by sitting in a marina reading books about cruising. You can’t develop confidence in your boat by polishing it, and you can’t learn what you’re capable of doing out there by imagining every possible thing that might go wrong. At some point, you’ve got to go. You have to untie the dock lines, point the bow toward the horizon, and start accumulating the experiences that turn a wannabe cruiser into an actual cruiser.
As Boris Pasternak once wrote, “Man is born to live, not to prepare for life.” I’ve always thought that was a pretty good philosophy for cruising. Life is happening right now, not next year when the boat is finished, not after you install the new electronics, and not when you’ve accumulated every spare part known to humankind and have enough money in the bank to eliminate every possible worry.
If you’re waiting for the perfect time to begin living your dream, you might want to consider that the perfect time is probably a myth invented by people who are afraid to take the first step. There will always be reasons to wait, things you haven’t finished, problems you haven’t solved, and risks you haven’t eliminated. You can spend the rest of your life preparing for an adventure that never happens, or you can set a date and start making it happen.
Then, when that date arrives and you’re ready to go, you can take a deep breath, cast off those dock lines, and find out what the world looks like from the other side of the breakwater.
As Franklin D. Roosevelt famously said, “The only thing we have to fear is fear itself.” Fear of the unknown is a powerful thing. It can keep you awake at night, fill your head with worst-case scenarios, and convince you that staying right where you are is the only sensible option. But once you begin experiencing the unknown, it becomes a little less unknown. You learn, adapt, and get better at making decisions, solving problems, and recognizing which dangers deserve your attention and which are just your imagination running wild.
Somewhere along the way, fear begins to give way to confidence, and confidence gives way to freedom. And freedom, my friends, is what cruising is all about.
It’s waking up in a quiet anchorage with no alarm clock, no commute, and no meeting you’re supposed to attend. It’s watching the sun rise over a strange island, meeting people whose lives are nothing like yours, and discovering places you never knew existed. It’s the satisfaction of solving a problem with your own two hands and the camaraderie of other cruisers who understand exactly why you crossed an ocean to sit in a remote harbor with a broken water pump and a smile on your face.
It’s learning that a good life doesn’t require everything to be perfect. It just requires you to be out there, participating in it. And the wonderful thing about cruising is that you don’t have to be a millionaire, a professional sailor, or some fearless adventurer who never worries about anything. You just have to be willing to start.
So if you’re sitting in a marina right now, staring at your boat and waiting for one more project to be finished, let me offer you a little advice. Finish the important stuff. Make sure the boat is seaworthy, your systems are appropriate for the voyage, your crew knows what they’re doing, and you’ve got the skills and equipment to handle the conditions you’re likely to encounter. Don’t confuse preparation with procrastination, and don’t let a departure date force you into taking risks you’re not ready to take.
But once you’re ready enough to go safely, stop looking for perfection. It isn’t coming. Set the date, make the plans, get your affairs in order, and when the day arrives, cast off.
Because the difference between dreaming about cruising and actually cruising isn’t the boat, the bank account, the electronics, or the number of spare parts you’ve managed to cram into the lockers. It’s the moment you finally let go of the dock. Once you do, you’ll discover that the world is a whole lot bigger, stranger, funnier, and more wonderful than you ever imagined while sitting tied to a marina slip.
There are thousands of cruisers out there right now, scattered across this big blue ball we call Earth, all sharing some version of the same adventure. Some are crossing oceans, some are exploring coastlines, and some are anchored in little tropical bays, wondering what they’ll fix tomorrow. But they all started somewhere, and every one of them had a day when they stopped saying “someday” and started living the dream.
So when are you going? Don’t tell me someday. Tell me the date, and then get out there.
The ocean is waiting, and she doesn’t give a damn how nice your boat looks at the dock.
