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Small Steps to More Adventure Than You Can Handle

Stefan Loble

With a keen thirst for getting out into the world, it can be tricky to connect with the adventure we need. Especially when expectations are so high. But, there was one time when I had more opportunities than I could handle…

I had already sailed to Bermuda from the British Virgin Islands, and was looking for a continuation of my journey. But, I had arrived in Bermuda without a fixed plan for how I would cross 2,000 miles of open ocean to the Azores.

In St. George’s Harbour, I borrowed a dinghy to row up to anchored boats and ask if anyone was going across the pond. And within an hour, I had four offers to crew on sailboats going my way.

An overhead view of Slow Shoes, the sailboat in the water.

Our Classic Westport 31, Slow Shoes.

As a 20 year old guy, I was elated. I felt like I could ride this train around the world and back forever.

In reality, it was all about timing, as there’s a circuit of boats that leave their winter Caribbean playground, head north to Bermuda in the spring, to summer in the Mediterranean, then eventually head back to the Caribbean again. 

Stefan at 20 sitting on a sailboat backlit by a setting sun

Me at 20.

Silhouette of Stefan looking over the ship at the horizonSeaside cliffs in the distance.

In the end, I joined a classic Westsail 32 named “Slow Shoes”, owned by two young Norwegian guys my age. Things that stick out in my memory: our wind steering autohelm, electricity we only turned on once every four hours to make a log entry, and hot bunking our night watches (one guy out of bed, next guy in). It was all I needed.

As you read this, you might be thinking of all the barriers between you and an adventure like this. Truth be told, I too can’t take off six weeks to go sailing right now.  But, there was a point when I was dreaming about this trip when all I saw were barriers too. 

I’ve found the best way to make a big trip happen is to start small - talk to someone who has done it, make a gear list, take a class, go on a smaller trip. Maybe book time off a year in advance! If you do this long enough, eventually one thing will lead to another, and off you go. 

You can do it. Hand-over-fist opportunities for adventure are out there. We just have to find them… one step at a time.

Bluff on,

Stefan Loble


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