Tips for New Cruisers

Whether you are a new cruiser or a seasoned passagemaker, these words of wisdom from an experienced sailor are something to ponder as you cast off.

Congratulations! You have conquered one of the strongest forces on earth: the iron grip of the land.

Your first cruising season will come with an array of adjectives: exhilarating, exhausting, energizing, confusing, exquisite, terrifying and life-altering, but it will also leave you with a mental scrapbook so beautiful and intense, your imagination will seem lackluster by comparison.

By now you’ve read it all; you’re jacked up, topped off and tanked up with anchoring tips, navigation principles and entire volumes of sailing advice, but take a deep breath and read this one last thing. My hope is that these hard-earned lessons will help ease the transition into your extraordinary new world. Fair winds to you, and send me a postcard.


Trust yourself. You have great instincts. They’ve just been buried under a heavy coating of civilization, a little self-doubt and years of neglect. Learn to listen to your own body, that small, wise voice in your head, the telling feeling in your gut. Nobody, no matter how experienced, is wiser than your own instinct. If it doesn’t feel right, don’t do it. Just wave as the other boats leave, pour a cup of coffee and enjoy your day.

Listen respectfully. You will get an overwhelming amount of advice from armchair sailors, from blog readers, from landlubbers and from seasoned sailors, a lot of it welcome and most of it well-meaning. Be respectful, pay attention and take it all in. Then go below, shut it all out and make your own decisions. Learning to be a good listener will serve you well in all aspects of cruising. Learning to make good decisions will save your life.

Pay attention. Retrospect will always tell you there were signs that something was about to go wrong. Be on guard when somebody says, “That’s strange,” like when the engine makes an unusual noise, or when the boat ahead of you going out the inlet is being tossed around like a child’s toy. Don’t hesitate to hesitate. If possible, slow down, turn around, question, regroup. Pay attention, process the information you have and then act on it.


Be open. You are going to meet hundreds of kindred spirits, more than you imagine, and many will become lifelong friends. Engage with people. Ask fellow cruisers about their lives, their families, their boats, their stories. Work on telling your own story, because you’ll be called upon to tell it over and over and over. (You’ll be so happy the next time you see an old friend who already knows your history.)

Reach out. Talk to the locals at every port, including the ports in your own country. The friendly sailing community can distract from the real reason you are out sailing: to experience other parts of the world, the people, the culture and the places. It’s not always easy to make an arc from the water to land, but with good intentions, a little practice and a kind heart, you can leave a trail of friends in your wake.

Ask questions. Know what you don’t know — and it will be a lot. The sailing community is not judgmental or critical. On the contrary, it will embrace you and offer advice, encouragement and a helping hand. We’re all in this together. Your fellow sailors will not only warm your heart and entertain you; they will be your best resource. Don’t be afraid to ask, in person or on the radio, and watch the dinghies come zooming.


One of the hardest lessons in breaking away from land is this: no more being all goal-oriented and get there, get there! You’re already there. Now is the time to slow down and drink it all in. If you allow it, cruising will teach you to live completely in the moment. It offers you the freedom to stay where you are until it’s not fun anymore, then meander to the next spot, sometimes only 5 miles away.

Go alone. Make your own decisions, even when you don’t feel confident, because that’s the only way to learn. Some will want to lead and others follow, but don’t let anybody’s plans or decisions interfere with your own. This will be incredibly difficult your first season, but every boat and crew has unique strengths, limitations and comfort zones. Meet up with friends at the next stop, but make your own choices and movements.

Embrace everything. Cruising isn’t going to be fun all the time. That pristine anchorage with turquoise water off a deserted island comes with a price. You are going to have moments when you hate your life choices, your boat, the ocean. You’ll abhor the wind, the waves, the swell, your spouse, yourself, and sometimes you’ll detest them all at once. It’s OK. It happens to everyone. It will pass — and make a great story.


Savor it. You’ll never have another first year of cruising, where everything is crackling with newness, where you learn something every waking moment (damn it!), where nature electrifies you with its beauty and its power, where you are overprepared, overstimulated, overwhelmed and overjoyed.

You have done an amazing thing. You had a dream, and you made it happen. You are the elite — when you leave the dock the first day, when you sail into your first foreign port, when you raise that brand-new Q flag and even when you’re yakking over the rail. You are awesome. Enjoy every single second of it. Every single second.

Tammy Kennon is a writer, sailor and traveler, now enjoying the bounty of the land with her husband in California’s Napa Valley. Follow her on Twitter @TammyKennon.

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