The Pineapple Cup is an 800 mile race that passes through the Bahamas and around the eastern tip of Cuba and ends in Montego Bay Jamaica. Distance races like the Pineapple cup are so much harder to but into perspective as opposed to the sprints or course races. This year I was a watch captain onboard the TP 52 "Decision" a Riechel Pugh 2nd generation design. She excels downwind but we were up against too newer designs in our class, a fellow TP 52 Samba Pi Ti and a IRC 45 Sjambok. Both of these boats are better suited for reaching conditions with wider stern sections that allow the boats to be driven harder while reaching. We corrected a half hour out second place under the IRC rating rule in the overall results. The Jamaica Race is a great test of every aspect of yacht racing, leadership, navigation, decision making ability and endurance.

Its been about 5 days since the finish of the race; we've had our debrief and there was a lot to learn about the boat in its first full distance race as "Decision". Obvious issues were some gaps in the boats sail inventory and adjusting crew members so that the boat has a proper backup at each position. There will be plenty of room for improvement in the next offshore race for the boat, the Annapolis to New Port race this June.

The weather pattern for the race was dominated by a cold front that came through Ft Lauderdale on Friday. The larger faster boats (including us) outran the front and ended up becalmed on Saturday waiting for the wind to fill in. Reaching conditions dominated the race and best suited our competitors Samba Pi Ti and Sjambok. We spent the majority of the race sailing between 110 and 140 degrees true wind angle, with wind speeds between 15 and 25 knots Sail selection was difficult as the boats cross over chart between optimal reaching sails is narrow. There is a careful balance between sailing outside the sails optimal range and changing sails so often that the crew fatigues and the change time outweighs the improvement in performance with the correct sail.

Without a doubt the highlight of the race is sailing around Cuba and sailing in the Windward Passage. Sailing towards Cuba we had a run in with a cruise ship. We contacted them via VHF radio asking if they could take our stern because in the open water it would have been easier for them to alter speed or course then for us to alter course enough to avoid collision. They denied our request and we were forced to luff main and spinnaker and sail off course for an agonizing 10 minutes. In open waters it is generally accepted that sailing boats have right of way over power boats including commercial vessels.

In hindsight this may have cost us second place overall, but over an 800 mile course 30 minutes can be recouped at many times this one just stands out in my mind. Shortly after rounding the eastern side of Cuba we encountered a prolonged period of wind speeds of 25 to 35 knots sailing at a true wind angle of 110 to 125 degrees. We reefed the main and changed from the Blast Reacher to the #4 head sail. The boat easily sailed at 15 to 18 knots under this set up. The Course to Montego Bay was 110 degrees TWA but I choose to sail the boat at a 120 to 125 degrees true wind angle for two reasons. First it was easier to deal with the waves at this angle (less pounding) and second eventually the trade winds would win out versus the cold front that was causing a more westerly breeze so it set us up to the left of rhumb in anticipation of the next wind direction shift.

The boat was jumping out of the water from wave to wave. Olympic Star sailor Andy Lovell suffered the worst injury. He ripped a good portion of skin off his index and ring finger in a particularly rough drop from one wave, at the time he was just hanging on to the life line. Moving around the boat was a risky proposition and there were a few scary moments where crew members would go airborne moving around the boat. Everyone stayed tethered to the boat throughout the night. Around 4 am it seemed the breeze was subsiding and I made the call to shake the reef, big mistake as shortly after this maneuver the breeze was back on 30 knots plus so right back to the reef. This was another area that could of trimmed time off our finish. Reefing on the "Decision" requires almost completing stopping the boat and having the main flog in the wind while the reef is sorted, not a good way to make VMG and not good for the mainsail. To say the least, I was not happy about putting the reef back in.

That same night in around the same area the 77 foot "Captivity" dismasted and retired from the race pulling into the US Navy Base in Guantanamo Bay Cuba. I have been lucky to have sailed the Decision in big breeze, the boat is solid and stiff. There was no point where I was concerned about the integrity of the boat, she is well built and designed, fast and responsive.

Monday morning the wind lightened up and started to shift right as we had predicted. We were finally able to start sailing downwind in 20 knots with the A4 spin and full main. Coming into Montego Bay on port gybe there were plenty of waves to surf as the left over westerly waves from the night before made for a slalom course. You could surf one wave at 145 degree TWA and then catch the next at 160 degrees TWA hitting speeds that matched wind speed. Starboard gybe was a little bit of a different story; on starboard the westerly swell was pretty much coming at you head on. On one particularly big set of three waves the boat sailed up the face of the wave and surfed down the back. It almost seemed like we were going to slip back down the wave like a surfer heading out from the beach in big swells. Another unique experience, thanks to this great race.

There are only a couple dozen of people who get to experience sailing passed Cuba helming a racing sail boat. It is the type of experience that makes everything else in life seem that much less exciting. The goals are clear get to the finish fast and get there safe. When you come home after the race you can't wait to go again and the rest of the world has the volume turned down. I feel very lucky to have completed three Ft Lauderdale to Jamaica Races since 2003 on quality boats and in progressively higher roles of responsibility that entrusted boat and crew to my experience and ability. Nothing I have experienced builds teams faster. It is a necessity to have a dynamic team that works together or the goals won't be achieved. Nothing establishes leadership roles more clearly than races of this nature. Unlike other sports, there are no bright lights, no fans, no coaches, so the motivation to push the boat must come from within the 12 crew members onboard the boat. Stephen Murray, the boats owner and skipper did a great job pushing the crew to sail the boat fast at all times. At the finish of the race we were greeted with the traditional case of red stripe and corrected out the 3rd overall under the IRC rating rule.

Another success to build on in 2007,

Respectfully Submitted,

Jack Jennings