The island of St Maarten was our intended destination, one-thousand miles to windward across the whole of the Caribbean Sea. Most vessels choose to follow the coast of South America toward Trinidad and then work their way up the Windward Island chain. Alternatively, others sail north along the coast of Belize toward Grand Cayman and work their way across the Leeward Islands.

Our approach was more direct. We beat to windward for ten days without stopping. Day and night we flew from the crests of massive waves and dove into the troughs that followed. The entirety of our existence was sodden and we came to understand exactly how it would feel to be a ping-pong ball in a bingo basket. Anything that was not bolted down gave way and crashed to leeward.

Three days into the ordeal, I consulted the oracle. “World Cruising Routes” by Jimmy Cornell described the passage as one of the most difficult legs around the world. Unfortunately for us, it discussed the route in reverse, with the wind from behind. We were committed though and continued slamming through the wild sea, altering tacks every 12 hours to see if life was any better if we leaned on our other leg.

Eventually, the boat began to protest this torment and some serious problems arose. First, the refrigeration pump was sucking too much air as the boat heaved and it finally drew its last breath and gave up. All of our food rotted, and we started living off of whatever cans we had stashed away for such an event. More seriously, our mains’l pulled itself from the bottom of its track and seized there. With so much wind and swell, it was impossible to fix, and we could not shorten sail despite desperately needing to. We needed a landfall and a decent meal.

On the ninth day, we laid her on a starboard tack and set our bow toward Hispaniola. The sea laid down considerably as we closed on the landmass and I threw a fishing line off the stern. Within hours, I glanced at it from the cockpit to watch as it bent in half and the reel started screaming.