Chasing the Dream to Circumnavigate

What does it take to sail around the world? For many cruisers, the dream of circumnavigating is where it all began. Whether they find bliss under countless stars far from land or anchored in gin clear Bahamian water waiting for the green flash at sunset, the allure of sailing the world got them there. What’s the next step to chase the ambitious goal to sail around the world?

With a successful circumnavigation under the keel, Jamie and I are often asked how we did it – how did we set out with three young kids on a small sailboat and keep going. We’re in our 17^th year of cruising; the first ten were occupied in making that loop. Over the miles, experience and observation bubbled up distinct markers for success among those who realize their cruising dreams, and in those who fall short of their goal. It is complexity in reach, but how? It is a fact that more people summit Mount Everest annually than circumnavigate under sail. It is also a fact that a young woman of 16 years completed a single-handed circumnavigation.  

The three-legged stool

Start with the big picture: in order to realize cruising goals, three fundamental elements must be in place. We’ve long referred to these dependencies as the three-legged stool. 

First, having enough money. Cruiser budgets range widely, so being wealthy isn’t the point. Affording the boat, necessary gear, and costs to support boat and crew is a must. 

Second, having sufficient health. How many ready to go cruising boats are listed for sale citing health reasons forced a change in plans?  

Third, having an amenable crew. Everyone on the boat must want to be there. Many partners want to be supportive, but need supportive effort to get to the dream on their terms.

There are many other elements to successful cruising but these three pillars must be in place to support a stable platform. One of those may change at any time. We particularly wondered about the last, as the needs of our children evolved in their teen years.

Finances

Ground your plans in financial reality. Can you make a plan to go with what you have now? If not, what does it take to get there? Stopping short for financial reasons is all too common. Make a plan and perform the due diligence around it. Mentors can help with realistic estimates; beware of enthusiastic ‘influencers’ or their media coverage on the topic, as they tend not to be representative of reality.

Land shedding

The work of letting go from land life for the duration of time you hope to be aboard is far more work than most folks anticipate. Leaving appears deceptively simple compared to the work of prep. Don’t underestimate the effort: it is not just the time it takes to pack up a home. Hard work and emotional decisions through all of the things of land life.

Boat selection and preparation

There is no ‘best’ boat for circumnavigating. There are the boats that suit your intentions, skillset, and budget. Beware of dogmatic opinions about must have features and gear, because they can impact your finances without the benefits for your cruising intentions.

Sailing skills

Learning to sail is easy and with some guidance and practice, sailing competency is not far behind. Competency in normal conditions that is. As I write this, we are broad-reaching on Totem 1,200 NM west of Hawaii in perfect conditions. Easy. We might have squalls of 40 knots overnight though, and that’s the thing about sailing – conditions change, often unexpectedly. Becoming a skilled sailor means some degree of competency with weather, boat-handling, piloting, etc. It also means the confidence to say I’m not sure, or let’s learn more before getting over our heads. It doesn’t matter how salty you are, there is always more to learn before conditions change.

Cruising skills

Many hopeful cruisers focus on sailing skills to the detriment of gaining the mechanical skills necessary for voyaging without drama. It’s easy to be complacent while professional support is in reach; that pro isn’t handy later. Success comes from learning systems, building practices for safety, and developing realistic seasonal routing plans. It’s knowing that offshore communications are more than installing Starlink, and that provisioning is more than keeping the crew fed. If you want to sail to remote places you must be able to fix ‘it’ or live without it.

Intangible skills

Much less obvious, but of equal importance are the intangible skills of patience, flexibility, situational awareness, and independent thinking. They go in hand with appreciating facets of voyaging life you cannot control. These skills don’t lend themselves to checklists and aren’t things you can buy, but are best developed through experience with mentorship and mindfulness. 

Realizing the dream

Once you have traveled, the voyage never ends, but is played out over and over again in the quietest chambers. The mind can never break off from the journey. (att. Pat Conroy)

Fair warning: cruising ruins lives… for the better. The shape of the dream often evolves along the way. The goal of our coaching service is to help cruisers realize their dreams, but sometimes that means an important recalibration to define “success.” It may no longer be fun, or feasible, to carve that notch claiming a circumnavigation, and that should be okay too.

Along the years to complete our own loop around the world, we learned that the accomplishment – while an achievement we are proud of – is not the ultimate fulfilment of our voyaging life. Stay open to declaring success in realizing your cruising dreams at a very different mark. What will matter are the experiences you find along the way: the lives that touch you, the vistas that take your breath away, and the encounters so mind-blowing you’ll struggle to describe them outside the tribe. But also, don’t lose sight during preparation for the possibility. It was the work of preparing ourselves for the possibility we could sail longer than a two-year sabbatical (whispers in the back of our minds… perhaps around the world?) that were key to right-sizing a shorter-term goal, so that it could morph into the larger one.

Behan and Jamie provide affordable, customized coaching services to help sailors realize their dreams to sail to the next island over or around the world. Find out more at TRU Coaching.