How teamwork during a sailing expedition rebuilt a family

In 2015, my kids were entering their mid-20s and due to divorce, moves, remarriage, and other changes, we were becoming strangers. I needed to own that.

So how to fix it? Answer: A sailing expedition.

My plan? Get them interested (and trained) in sailing with the carrot of a week’s vacation in the Caribbean.

We lived in Minnesota, so warm weather was the right bait.

It turns out through the magic of sailing certifications, training, and the bareboat charter industry, you can fly to the Caribbean, provide a credit card, and you effectively own a 20,000-pound, 40-foot, twin-hulled sailboat for a week.

This trip was the first where I was the captain and my kids were the crew. Sailing and operating the boat were 100% on us.

We were ready for the challenge.

But we had a lot to learn. And we had been sailing through darkness, for years.

Truth is, we didn’t know each other anymore.

We landed in the Charlotte Amalie, USVI, then transited via ferry to the British Virgin Islands where our boat was located.

To be honest, the boat and the environment were very intimidating.

Although we had sailed in the BVI the previous year for training, the boat was now my responsibility, 100%.

All 10 tons of it, and although the BVI is a the world’s most popular cruising ground, the seas get big, 4-8 ft is common.

But that’s the essence of an expedition: you are pushing past your comfort zone into an unknown. Even if it’s known for others. If it’s not known to you, then it’s a (light) expedition.

After adjusting to the boat and it’s idiosyncrasies, the first few days went very smoothly. We certainly enjoyed the 100+ degree temperature difference, from -20 F in Minneapolis in early January to 84F in the BVI.

We enjoyed all the delights of sailing the Caribbean’s finest cruising ground: wind, beautiful anchorages, and sunsets.

But the best part of the trip was the most stressful & challenging, and came on the third day, when we headed to Anegada, an outer island surrounded by reefs.

And this is where things got interesting. What we had experienced so far was idyllic; that was about to change. The skies darkened, the wind picked up, and we had to push through a big storm, big seas, and dangerous reefs to get to the best part of the islands: Anegada, and it’s endless, glistening white sand beaches.

During that part of the voyage, both my son and daughter played critical roles. My son stayed calm and found the outer buoy leading to the safe channel into the island’s only harbor. My daughter learned the right holding strategy from other boats when the visibility went to less than 100 feet (just hold in position, right into the wind, until the squall passes), and schooled us on it.

They tempered my worst tendency: to just stick with the strategy and force things, rather than adapt to circumstances.

We were soon rewarded with a gorgeous anchorage which, post-storm, was awash in rainbows and glistening white beaches.

Since this was an expedition, it required teamwork to complete the mission.

That teamwork reunited my kids and I, the success we had rebuilt trust and love, and the gorgeous natural surroundings cemented that love.

Conclusion

Most travel today is focused strictly on maximum comfort in known surroundings. Expeditionary travel is different: it’s about learning new skills, applying them in strange, unfamiliar environments, and adapting and growing in the process. It should be mentally and physically demanding, at a level that is appropriate for you.

Too much comfort is the enemy: it’s why we have an epidemic of obesity; it’s why being outdoors is so strange to so many of us; and why we focus so much on removing risk from our lives. The pervasive ill health we see today, including mental illness, is partly due to this incessant search for comfort.

By learning sailing skills and then applying them in challenging situations with some risk, a great thing happened. I was able to rebuild my relationship with my kids via the teamwork required in a difficult situation, build my own confidence, and most importantly, get ready for the next challenge.