They look like a pine cone and taste like heaven. The pineapple was likely first grown in South America but was widely cultivated across the Caribbean by 1493 when Christopher Columbus, on his second trip to the New World, brought the first one home to Europe. The strange fruit caused a sensation, one that the canny Columbus knew helped his efforts to secure funding for additional exploration.

Despite best efforts, the Europeans failed to be able to cultivate the fruit at home and the Caribbean basin remained the sole source for pineapples until the Spanish introduced them in the Philippines. In the meantime, the only way to get the treasured fruit was to ship it. In the absence of refrigeration it meant that most of what arrived in Europe or their new American colonies was preserved or sugared fruit, but every now and then a fresh pineapple would turn up. Fresh fruit was so rare, it was reserved for royalty or deep pocketed patrons, and often times a single fruit would be rented out for display at parties before being sold to a syndicate of hungry fans.

A host offering pineapple to their guests was a sign of unsurpassed hospitality, and soon enough the image of the pineapple alone became a symbol of hospitality. Painted on signs, carved on mantels or cast into bronze door knockers if you saw a pineapple you knew you were looking at someone who valued a warm welcome.

So it’s no surprise that this race is known as the Pineapple Cup - Montego Bay Race. After 4 days of hard and fun racing, every boat that pulls up to the dock is welcomed by an enthusiastic crowd of Montego Bay Yacht Club members and a case of cold Red Stripe. Each boat is hosted by a member and their family, and everyone goes well out of their way to make you welcome and help solve the inevitable list of issues that crop up when you take a boat a long way from home. The hospitality is the best of any race I have ever been involved in, and it’s a big reason to keep coming back for more.

Tonight’s the prize giving, wrapping up Dragon’s fourth edition. I fly home tomorrow and then Rob will deliver the boat back to Key West where she will sit for a few more weeks until Miami to Havana in March. I hope the adventure was fun to follow – until next time.