From the time I could read, I was in love with the pirate life of the Caribbean. Treasure Island, later pouring over old charts of the islands and pirate listings in the encyclopedia, hours spent reading old National Geographics during detention in the library. Then we moved to Florida and things got serious. I got my first daysailer as a teen. I found small, uninhabited islands in the bays and mouths of rivers after school. I camped and fished on those islands on the weekends, like a sailor marooned back in the day.
As I got older, the boats got bigger. By December, 2012 I had a 42 footer under me and had spent the last few years using all my vacation time doing short hops along the Gulf coast. Thirty mile overnighters, became week-long voyages, then trips to Key West, New Orleans, Galveston and back. I’d long ago left my childhood pirate fantasies behind.
On 17 December, or so, I offered to give a lovely British lady a ride to her yoga clinic across the water on the Yucatan. I was in a bit of an existential crisis, I was looking at retirement in the eye, I’d just broken up with an amazing woman. Over the past three years, I’d sold off my townhouse and moved onto the boat, got rid of a lifetime of flopsam jetsam, stipped my life to the bone. Plans had not yet been finalized.
When we arrived at her place in Celestun, Mexico the newspaper headlines, an inch high in Spanish, in the vending boxes on the dock, announced that some kid had gone nuts and shot his mother and twenty first and second graders at a school in Connecticut. Fuck. Not again. It gnawed at me for two days while I stayed with this gorgeous and wise Brit.
While heading back to Key West, about 200 miles out in the Gulf, the afternoon sun baking my back and the water and wind taking me home, I had a moment. I didn’t want to go back. I was 59 and this urge that it was now or never hit me hard. It felt like my personal constellation of guiding stars had suddenly lined up. I had already had one heart attack, how much time do I really have left? I began thinking about those pirates. Those magical islands were only a week or two away to the south. I was experiencing an actual physical reaction, a bit of shaking, a rush of blood, slight dizziness. I was actually struggling with my thoughts.
Fuck it, I’m doing this. I pointed her bow to the Yucatan Strait, that channel packed with strong currents between Cuba and the Yucatan—the gateway to the Caribean. The boat lurched under me as the sails suddenly caught the wind with a pop after making my turn. I was on my way. It felt like it was the first time of something, like sex, or like when you turn the engine over on your first car. I didn’t give a shit if I died doing this, it was better than being found in my lounge chair with a remote in my hand with ESPN on the TV.
I bounced off the islands for two years. I finely found the one I liked best. I still do a lot of distance sailing. But I’ve never sailed her back to US waters. Been there, done that.
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