Five hints to kick-start your cruising dream.

The dream is to sail offshore. To live on board and cruise the world, living the simple life, fishing, and idealic anchorages. You’ve done a bit of sailing, you’ve followed all the YouTube channels, you have read about people who have embarked on such an adventure, and you’ve even bought a boat. But… the kids are in school, you still have a mortgage, and that job has a golden handcuff around your wrist. Not to mention your aging parents, your friends, and all that important accumulated “stuff” that has filled your house over the years. How do you actually realise that overwhelming dream? It’s a bit like the question of, “How do you eat an elephant?” The answer is, “one bite at a time.”

On a personal level, our offshore, liveaboard lifestyle has evolved over the years. It started with buying our first boat when we were in our early 20s. We lived on board to save money, which in turn would enable us to take time off work and achieve that first offshore Pacific Island adventure.

For us, the boat came years before we bought a house. Then, after having children, we bought a bigger boat (the one we’ve had for more than 20 years). It’s not the flashest or the biggest in the cruising fleet, but for us, being out there and “doing it” is more important than having a floating apartment with every mod-con.  Essentially, we’re camping, but it is quite comfortable camping. Thinking back, goodness knows how five of us lived on board for so long. 

1. Timelines: Preparing for a life afloat can seem more achievable with a timeline. Populate your timeline with some tasks. Make an achievable calendar to work towards. For example: Fix one system on your boat before summer, sell one unnecessary possession, take one course, or start a savings plan. It’s very satisfying to tick jobs off your list and see some actual progress as your list gets smaller as the year progresses.

2. Finance: Many sailors believe that money is the biggest barrier to achieving their goal, whereas often, the biggest barrier is hesitation. Spend some of that hard-earned money on skills, equipment, or preparation, and suddenly, the idea becomes a real project. Suddenly, you have some skin in the game, and you’ve committed. Obviously, money helps. Boats are not cheap to run and maintain, and everything costs more than you optimistically expect. Whatever decision you make, there will be some compromise. It’s a matter of working out what you are not prepared to compromise on.

3. Physical Ability and Health: Many sailors finally reach a point where they feel that their finances seem secure enough, and they’ve retired from work, only to find out that their bodies start letting them down. Get as fit, flexible, and strong as you possibly can. Sailing is a physical activity. Try putting some fitness goals on your timeline. Think about budgeting for health insurance coverage. It becomes more expensive the older you get, but it does provide peace of mind if you should suffer a medical emergency while you’re cruising, or even if you need to visit the doctor.

For me, the catalyst for truly committing to the goal of embarking on a circumnavigation was cancer. At the age of 48, I was diagnosed with breast cancer and spent 18 months going through chemotherapy and surgeries. It was the “holy crap, I might die before I reach the age of 50, and all I’ve achieved is a promotion at work…” moment. The positive side of a cancer diagnosis is that it gave a certain urgency to achieving the goal.

4. Letting go of some “stuff”: Do you really need your enormous house? Could you downsize? This could free up some cash. Could you rent your property out and generate an income while you’re away? Are you courageous enough to make those changes to your comfortable, familiar life? It’s about choosing the life that you’ve imagined, not waiting until that perfect moment…which will actually never come. 

5. Having a fall-back position or plan:  Make a plan in case it all goes bad. Ensure that you have enough money and a place to go if the unexpected happens. The unexpected happens more often than you think. In recent times, there were the COVID Years. Some offshore yachties found themselves locked down in foreign countries or having to return to their home country, leaving their boat at short notice. What if you have an accident or the boat is damaged? What if war breaks out? 

If you are embarking on this life-changing project with a partner, one of the biggest questions to ask is, do you both share the same dream? Do you both have buy-in? Are your expectations of liveaboard life the same? Are you both committed? 

We found that having different areas of responsibility and work makes for a happier, well-run boat. For example, who is the navigator, who takes the lead with provisioning and cooking? Are you both confident in driving the boat, trimming the sails, and watch-keeping? Ask the question: Are you just along for the ride, or do you engage with the decision-making?

For me, it was too big a step to resign from my job and commit to doing a circumnavigation. I loved my job and my ordinary humdrum life, but you don’t know what you’re missing until you try.  I dipped my toe in to see if the lifestyle was what I imagined.

I was granted twelve months’ leave without pay from my job. We rented out our house and used the rent money to pay the mortgage and cover our living expenses. I ended up going back to work for several months when the tenants moved out of our house, and we were unable to find anyone to move in. We literally ran out of money! We left our boat in Langkawi at Rebak Marina. Returning to New Zealand, we went back to work, regrouped, and made the life-changing decision to sell the house. 

The feeling of financial freedom was amazing after the house was sold. We had no debt, and we were not chained to a job, and I really did not miss my house or my stuff. Being financially free opens a world of opportunity, but of course, it comes with sacrifice. Opting for a simple life on board our little floating home suits us right now, but things always change.

Each circumnavigation, each ocean crossing, and each departure from the dock begins in the same way: one decision, one task, and one small step. There’s always a reason to wait. The timing will never be perfect. The boat will never be perfect. Life is rarely perfect. The danger isn’t that the dream will disappear – It’s that it quietly slides into “some day….” And “some day” has a habit of quietly drifting offshore with every passing season.