This is part two of the Living the Sailing Dream Series. You can read part one here.

Did I let go of the other half of my ticket from New Zealand back to the states and hop on a boat to Papua New Guinea? I often wonder what would have happened if I did.

It wasn’t until I found myself on Utila, a tropical island in Honduras, learning to scuba dive, that the opportunity again arose to crew a sailboat. And here’s where the adventure really began.

What should have been a short, easy trip turned into a more dangerous journey.

Throughout the next few years, I traveled around the world, getting side-tracked from sailing by land adventures, romances, and exotic locales. These were the days before mainstream Internet use. Back then there was not ready access to yacht crew websites such as,, or

There was an odd guy who lived on Pegasus, a 53’ schooner anchored in the harbor. She was a sleek stranger with her teak wood decks, generous cockpit, and dark blue hull. And I only knew Tim a little better. One day he decided it was time to head back to Clearwater, Florida, and he needed a crew to help sail her back.

I thought back to the time I’d passed on the crew position to Papua New Guinea, now five years past, and didn't want to risk losing another opportunity. I talked a friend with more sailing experience than me into going. There was also a Canadian and an Australian with sailing experience, a smelly Scotsman who turned out to be deadbeat broke (and didn’t pay for his portion of food and fuel), and a British couple with no sailing experience hopping a ride to Mexico.

Thankfully my friend, the Aussi and the Canadian all had strong sailing skills — because it soon became apparent the owner did not!

Due to tides, a deep draft, and shallow areas around Isla Mujeres, we took off in the middle of the night from Utila in choppy seas to head first to Isla Mujeres, Mexico, before making our way to Florida. This short sail became four days with a very treacherous approach. We soon realized that Tim had no clue how to read a nautical chart, and his GPS only worked intermittently. We entered the channel at the wrong angle, we were so far off the mark we were lucky we only felt a few brushes here and there without running aground.

Ignorance is bliss, or I would have gotten off the boat there and then. Nowhere in our itinerary was a detour to Cuba, but what happened next is the thing “there I was” stories are made of.

— Leah Kaiz

Read part three of Living the Sailing Dream next Tuesday.