Bucketlist Sailing

It’s true, I love productivity, but sometimes I can work too much, and it’s a mistake to miss life. We only get one.

I also love adventure, and earlier this year that’s exactly what I needed.

A lot of changes were going on in my life. I had just turned 30, finished a job in San Francisco, my wife had taken a medical training position back in Melbourne, and it was time to move. I looked at my bucket list - mostly unedited since I wrote it - at the raw and restless age of 21. Near the bottom, one line stood out to me

sail across an ocean

I had never sailed, never even been on a sail boat, but the words stared back at me. Why hadn’t I? Literally nothing was stopping me. That’s a clarity that grows with age. Appreciation of your own agency, and a steady respect for what lies outside it.

So it was decided.

I called a friend living in Europe.

Phil: “Want to go sailing in Croatia?…"

Henry: “Hell yeah I do”

Within a month, I had taken some sailing lessons, aquired a VHF license, studied charts and weather, organized a boat, and found myself in the beautiful ancient town of Split on the Dalmatian coast.

Nothing quite compares to the feeling of setting off in a small sail boat, a good friend onboard, the sun rising behind you, and the open sea ahead. We had little, if any, real experience. Just the 21-year-old youthfulness of a bucket list item, and the courage to take it on.

On the first day, the wind caught us by surprise. More powerful than we expected. White knuckled, we furled the jib. As we rounded the headland the wind died down, along with our fear. Settling into the feeling of being reponsible for our own lives, we made way downwind, growing familiar with the motion of our little boat, and cleaning up the pasta bag that had exploded down below.

Each day was a new journey. The route planned out the night before by carefully studying the forecast and charts.

Each day we grow more confident. Fear was replaced with knowledge. We learned how to trust the boat, and each other.

Crossing to Stari Grad we sailed into a city over 2000 years old. Following the path of the ancient and intrepid sailors before us.

On the last day we set off to a blue sky, with a dark cloud to the west. An hour later, lightning was striking a nearby island, and half the sky was black. We were being chased down by three locally formed thunderstorms.

Fear returned.

We raced forward, under engine, following the instructions of our boat owner. Aiming for a small gap between the storms. He sent us a line drawn on a screenshot. “If the first storm has not passed when you reach this line, wait in the open ocean”. A highly unpleasent proposition.

It rained and rained. The waves crashed on our bow. We tied ourselves to the deck. Afraid that if we fell in, we would not be found in the mess around us.

We lost visibility. I started to steer the boat with its compass, a device that had suddenly transformed from ornamental to fundamental. For a moment I lost course and started bearing west. Henry noticed, shouting over the sound of the rain and the crashing of the sea.

“You’re not going North!"

Surprised, tired, and cold. “I am going North!"

“Look at the compass! You’re going fucking west!!"

He was right.

Eventually, we made it. We are the main characters afterall - on this 21-year-olds bucketlist.

A gap in the sky cleared ahead. We rounded the same headland that nearly blew us over when we started. The water calmed. We listend to the thunder around us and followed a line of bare pole sail boats scuttling into the safe water.

By the time we made it to the marina I was soaked through.

We made a pot of very hot coffee below deck. I slowly warmed up and looked across at Henry. He grinned back at me.

“That was AWESOME”