FAQ: What advice can you share with dreamers?

Not surprisingly, we get questions from people all the time, asking us how to get started on a sailing dream. Sometimes the questions are from people who have never sailed in their lives, and often they are from families, people who want to break free from the “system” but are not sure how to do it.

We like to think of ourselves as part of the welcoming committee for people looking to live aboard and cruise with large families. We think this is a great lifestyle and an achievable dream for many. But it’s not for everyone. There are certain traits necessary to get—and keep—the ball rolling. And an ability to sail is not necessarily a prerequisite; anyone can learn to sail, but not everyone can live in a tight space with their spouse and numerous progeny and cope with frequent breakages, unpredictable weather, discomfort, and constantly changing plans. These are challenges about which we have tried to write with honesty and good humor, but they are indeed challenges, and there are moments when Jay and I feel completely inadequate and wonder why we thought we could do this with five children.

If you’re contemplating sailing away with your family, there are ways to find out if you are ready to take on an adventure of this magnitude. There are baby steps to take now, and giant leaps when you’re ready. Of course, the advice we offer here is experiential, well-reasoned, and logical, but sometimes the most successful adventurers are those who defy logic, and just go out there and do it, those who ignore advice like mine.

That said, we would still argue that there are common traits we find in fellow cruisers and live-aboard sailors which make them successful. Someone once told me that the test for boat ownership is a willingness to take all one’s money and stuff it down the shower drain and turn on the water. Now that we own a boat, I would say that’s not far from the truth. Aside from holding less tightly to one’s material goods, three things must be present in order to leave a land life (whether for a short time or for the long haul), and start a sailing adventure: the simultaneous abilities to dream big and to take small steps toward an end goal, and the ability to push past the inevitable obstacles.

If you are reading this post, you’re probably already dreaming big. (That, or you’re somehow related to us, and for following us faithfully, we thank you.) There are two kinds of dreams: the night kind, with fuzzy edges and images that are hard to remember, vague and undeniably romantic; and the day kind, a crisper, clearer picture formed by your conscious mind. Dreaming only of sunsets and clear water and a fish on the line isn’t enough. You have to have a really good mental picture of what your live-aboard life might look like—a sort of snapshot that you can come back to and stare at when all looks bleak and impossible.

After you have your idea and have somehow gotten your spouse and family on the same page (their support and enthusiasm are of critical importance), you have to then take your mental snapshot and draw a flow chart on the back. What are the steps you have to take to get closer to sailing away? Things to consider are finances (Are you free from debt? Can you work while you travel? How much will this cost? What will you do with your house and belongings?); comfort with discomfort (Can you live without air conditioning and long, hot showers? Would you mind hand washing dishes and clothes? Who in your family gets seasick?); and skills (Do you know basic first aid? Can you sail? Do all your kids swim well? Can you fix things? Will you homeschool?). Sometimes the answers are unknowable until you’re in the thick of it, but in most cases, you can begin to alter course degree by degree, trying new things (taking a sailing class, going on a long family vacation in an RV, not using the dishwasher, downsizing to save money for the boat) and making small decisions that will get you closer to your goal, like setting a deadline and making a yearly plan (then sticking to it, or your dream will never make it out of La-la Land).

Lastly, hold tenaciously to your dream and your plan. Ignore nay-sayers, even if they are in your own family, look for people who share your passion and learn from them, and recognize the obstacles to your success and surmount them. Read lots of inspiring stories, and stories of survival. Things will indeed stand in your way, and leaving a normal life will be harder than you think, but you must be more persistent than your circumstances.

I would be remiss if I did not mention that through all of our phases—from castle in the clouds to the reality of living aboard at the dock to island hopping in the Bahamas, we have prayed for guidance. Many times our faith has gotten us past our fears and sometimes wisdom granted has saved us from foolish mistakes. We have prayed for friends and our lives have been filled with fellowship we might not otherwise have found. We have been filled with gratitude for safe arrivals, natural beauty, unexplainable “coincidences,” and good health. All the advice in the world is no substitute for an earnest and humble prayer.

Other suggestions for the dreamers out there:

• Read Cruising World magazine, anything by Lin and Larry Pardy, and Tom Neale’s All in the Same Boat. Read Voyage of the Northern Magic to get an inspirational story of a Canadian family that circumnavigated the globe with almost no experience.

• Go to boat shows—we like the Strictly Sail Shows. Crawl around on different boats. Meet real people who do what you want to do. Buy a signed copy of a sailor’s book.

• Watch inspiring family movies like The Astronaut Farmer or episodes of Paul and Cheryl Shard’s Distant Shores.

• Take a crewed charter vacation on a sailboat before taking any life-altering steps. It will offer invaluable insight about whether or not you will love living on a boat and may even raise questions you haven’t yet thought to ask.

• Make a five-year plan if you’re starting from scratch. That’s about the right amount of time for learning, saving, practicing, shopping, and downsizing.

• Write about your experiences as a way to document the changes you go through, keep a record of good memories, and inspire yourself if you get discouraged. Maybe it will be inspiring to someone else someday and the whole thing will come full circle. Funny how that happens…