by Barbara Theisen

You imagine yourself sailing off into the sunset someday. You close your eyes and spot a tropical paradise on your mind's horizon. Once again you find yourself sailaway dreaming.

There's a whole world out there for you to discover and perhaps you believe a sailboat will give you the means to achieve this. Maybe you yearn for adventure or want the feeling of self-sufficiency and independence that cruising can give you. If you have children, you might be searching for a way in which you can slow down and enjoy quality family time.

The reasons for sailing away are as varied as the sailors who dream them. Whatever your reasons for wanting to live the cruising lifestyle, your family and friends just might think you're crazy. But if your dream is to sail around the world, or to sail off for a couple of years, then listen to your own heart and go for it.
Although many people have the dream, few will ever attempt to make that dream a reality. If you believe you're one of the few, you'll be happy to know that mega bucks and oodles of sailing experience are not the two most important things to start with (although you will have to obtain some of both). More important qualities are independence and an adventuresome spirit and perhaps the most important quality, a belief in yourself and your dream.

Kate Theisen holds a spiny lobster that her dad speared.

"To accomplish great things, we must not only act but also dream; not only plan but also believe." Author Unknown

If you truly believe in your sailaway dream then you're already on your way to making it come true. Next you'll need to obtain a boat, a cruising kitty, and sailing skills (or whichever of these you lack). If it's not any of these things that are keeping you from pursuing your dream, then you'll need to examine what it is that keeps you from casting off the docklines.

What's Keeping You Tied to the Dock?

Too old, too young, have kids, don't want to give up the security of a job, retirement worries, the list goes on and on. All of these reasons for not going can be overcome. Everyone who has sailed away has overcome difficulties.

But sailing to the far corners of the world is not for everyone. Perhaps there are alternatives that would suit you better. How about a summer long cruise instead of your annual two-week vacation? Maybe an exotic charter would cure your yearning for paradise. Some cruisers sail as far as their limited time allows and leave their boat there. They return the following year to resume cruising to a new destination and leave the boat until they can again return. Your sailaway dream can be whatever you want it to be.

I've also heard people say that they'd go BUT their spouse would never dream of it. This comment more often comes from the husband. They want to know why I dreamed of sailing off and how they can convince their wives to share their dream. I tell them that I love adventure and travel and truly believe that the cruising lifestyle is a great way to raise our two daughters. But I also know that my husband Tom, whether on shore or on the water treats me as his equal. I know that when we step aboard he won't suddenly become "super captain" while I'm demoted to galley slave. He values my input and ideas and trusts my judgement. And time and time again he has shown me that I can trust his judgement. The work and enjoyment of living aboard and cruising is shared by all of us.

I also think it might be wise for a husband who dreams of sailing away to look at things from his wife's prospective. This may be a new millennium but most women will still find they do the majority of cooking, shopping and laundry. Your dream may include visions of an exhilarating downwind sail to a tropical anchorage followed by a relaxing evening in the cockpit drinking the local brew until the "pink light is gone." Your wife may simply see the disappearance of her microwave, washing machine, and corner supermarket. So if you want your wife involved in your sailaway dream, be sure to get her in on the planning of the dream. Discuss improvements to the galley. Find out what would make your boat more of a home for her. Talk about where she would like to sail to. Consider her needs and be sure to ask her about her fears. Then take her fears seriously. Make the dream a joint venture.

Sailaway dreamers anchored in the southern Bahamas.

"If you have a dream, follow it. If you catch a dream, nurture it. And if your dream comes true, celebrate it!" Author Unknown

We started with nothing but the dream. But eventually you will need skills, a boat and a cruising kitty.

1. Start acquiring the skills necessary for your dream journey. Keep in mind that sailing is a lifetime learning experience so don't expect to know it all before you leave. My husband and I had virtually no sailing experience when we decided we wanted to live the cruising lifestyle. But we knew these were learnable skills. When you first start out, having a belief in yourself and your dream are more important than knowing how to hoist a sail.

Reading is a great way to begin if your sailing experience is non-existent. Courses in navigation, a power squadron class, or attending seminars at a sailboat show are all great ways to add to your growing sailing knowledge. Next start putting some miles under the keel. If you don't have a boat yet you can try a sailing school, a charter, or sail with friends. If you don't know anyone who sails, you might sign up to crew at the local sail club. This will get you out on the water and will get you in the company of fellow sailors. Perhaps racing is not your end goal, but none the less you will learn valuable sailing skills and you may meet some cruisers.
If you have your own boat, spend as much time as you can strengthening your sailing skills. If you're a couple, be sure to practice a variety of skills - don't always be the helmsman when docking or the one who reefs the sail. Be sure both of you know how all systems on the boat operate.

The more independent you can become the better. Now's the time to start acquiring skills such as engine maintenance, sail repair, head repair, etc. You don't need to have all these skills immediately, but if you're spending a couple of years saving money for your sailaway dreams, you may as well use that time wisely.
Many cruisers have to work from time to time to supplement the cruising kitty. Portable occupational skills are other skills worth acquiring. You may also want to pursue interests such as scuba diving, photography, learning a foreign language or getting your ham radio license - activities that will enhance your cruising.

2. Get yourself a boat. You need a seaworthy vessel and one on which you feel comfortable living aboard. I won't go into what makes a boat capable of safely sailing the oceans. There are books out there that will tell you this. Size is not important either but I think it's important to be comfortable. Comfort to the solo sailor and comfort to the family of five will most likely differ, just as what is comfortable for one couple may be unliveable for the next. Also what might be suitable for a nine-month sabbatical may not be what you would like to call home for the next ten years.

Most people do have to settle for less than their ideal boat. Start with whatever you can afford. Perhaps you'll find that you don't need everything you thought you did.

"The perfect boat is not the one you dream about. It is the boat that takes you cruising." Don Casey and Lew Hackler, Sensible Cruising: The Thoreau Approach.
I don't recommend burning all your bridges, buying a big cruising boat and taking off. People have done it but the chances of success are less then if you take it one step at a time. Tom and I bought our first boat, a Balboa 26, while we were still living in the middle of the Colorado mountains. It gave us a chance to find out if we liked sailing and to acquire some sailing skills without selling our home, quitting our jobs, and pulling up our roots. Knowing when to cross a bridge and when to burn one can help you succeed.

When choosing a boat or upgrading your existing one, remember to take a good look at your different boat systems. Strive for independence. The more self-reliant you can become, the better.

3. Save money. This is the hardest step for most people. While choosing your new home afloat and strengthening sailing skills by sailing off to your favorite anchorage are fun - saving money means hard work. But again, if you believe in your dream and are willing to put in that hard work, you will eventually get where you're going. Here are some ideas to help you build a cruising kitty.

If you have a boat, live aboard it. This will accomplish several important things. You can save money by renting your present home or saving rent that you would otherwise pay; you get to know your boat - really know your boat; and it gives you a chance to see what you think of living aboard. 

Get a second job. While we were still "sailaway dreaming," I took an evening job as a bartender so I could stay home with the kids during the day. I did freelance writing during nap times. Tom had a great job as a computer specialist but would pick up whatever he could on the weekends. He worked as a carpenter, a bartender and as a computer consultant. Everyone's financial situation is different, but you'll find that most people have to put in an enormous amount of hard work to make their sailaway dream a reality. I don't know any short cuts in lieu of hard work and making some sacrifices. 

Drive a beater. Start thinking of a car as nothing more then transportation. Perhaps you don't need a car at all. Having no car payments and lower insurance rates can save you a bundle of money Tighten your budget and remember to make a monthly payment to your dream savings account. 

Two cruising boats anchored in Canada.

You'll probably have to give up certain things you've become accustomed to in order to supplement the cruising kitty. But your sailaway dream is worth it. Take a look at where your money is going and make some tough decisions. Perhaps you can eat out less often, maybe you can reduce your clothing budget (you won't need much when you sailaway anyway), how about brown bagging it at lunch, etc. Go to the library and check out a book or two on how to reduce your bills and how to save money. The little things really do add up.

"We can always live on less when we have more to live for." S. Stephen McKenney

Keeping the Dream Alive

Sustaining your dream can be tough, especially if you need several years to obtain the skills, boat and money necessary to sail off. Remember, most people can't imagine doing what you're doing. Their minds are not able to envision what you see beyond the horizon. Yet, here you are taking positive steps towards making your dream a reality. Give yourself lots of pats on the back for your accomplishments, however small they may seem.

It's important to enjoy the company of those with similar dreams or anyone who supports you in your dream. Being constantly surrounded by people who tell you how crazy you are, how you'll never succeed, and by those with nothing but negative feelings towards what you're doing is very defeating.

But remember that your dream may be sprung upon family and friends quite suddenly. Give them time to accept it. Many of their negative comments are probably genuine concerns. I suggest that you give your dream a lot of thought and formulate a plan before you tell others about it. Then you will be prepared to answer their questions and concerns.

Tom and Kate enjoy a sunset row in the dinghy.

I was very hurt when Tom's and my parents didn't jump for joy at the idea of our sailaway dream. My mother seemed to ignore the whole thing, hoping we might just forget about our "crazy idea." Tom's mom kept coming up with what she thought was the ultimate reason we couldn't go. Her last one was "the kids will be of school age by then, you can't possibly go." But eventually they came to accept our dream and support us. In fact my parents are now planning their own retirement cruise and my mother-in-law, who we won over to the idea of homeschooling, expanded her job as a university continuing education counselor to include distance education for high school homeschoolers.

I also kept motivated by reading accounts of other people who had pursued sailaway dreams. Imagining myself in a similar adventure was a great morale booster.
But the biggest motivator of all is to start living the dream right now. It doesn't matter if all you've done so far is get out a notebook to write down your sailaway dream goals.

It's been fifteen years since my husband first popped the big question "do you want to go sailing for awhile?" Our life hasn't been the same since. It took us five years from the conception of our dream until we moved aboard our 41' Gulfstar, Out of Bounds. We've spent the past ten years aboard - cruising, raising our children, and living our dream.

So often I've read "if you want to sail away, do it today, don't wait." Unfortunately, most of us just can't afford to do that. But that doesn't mean you'll never be able to do it. If sailing away is your dream and you truly believe that you can accomplish that dream, then taking it step by step will get you there. It may take years. Enjoy those years. They're all part of the dream. 

Barbara Theisen has spent the past ten years living aboard Out of Bounds with her husband Tom and daughters, Kate and Kenna. Out of Bounds is presently in the Rio Dulce of Guatemala. 

Visit the Theisen's website at