Heavy hitters for the Pineapple Cup

The new Donnybrook set to lead the field down to Jamaica

The 31st biennial Pineapple Cup–Montego Bay Race presented by Appleton Estate Jamaica Rum is living up to its reputation as one of the marquee offshore sailboat races in the world by, once again, welcoming a fleet of high profile boats, both newcomers and veterans, to compete.

Starting on 8 February, just outside Fort Lauderdale, this ocean racing classic will take competitors on a challenging all-points-of-sail course, stretching 811 nautical miles to the legendary destination of Montego Bay, Jamaica.

“This has been called the most interesting race because you are almost never out of sight of land the whole time,” said Race Chairman Ken Batzer, adding that the iconic race was established in 1961 and has been running either annually or biennially ever since. The current race record was set in 2005 by Tom Hill's Titan 12 with an impressive elapsed time of 2 days, 10 hours, 24 minutes and 42 seconds. “We have a real quality fleet once again this year and are hoping to have good weather.”

Past winners of the event include some of the most world-renowned skippers; Ted Turner won three times in Vamoose (’67), Lightnin (’73) and Tenacious (’79); the Johnson family won in Ticonderoga (’65); John Kilroy won twice in Kialoa (’75 and ’77); and Jack King won in Merrythought (’91). Past competitors taking line honors include Sir Peter Blake on Condor (’79), Larry Ellison on Sayonora (’97) and Roy Disney on Pyewacket (’99).

Return contender Tom Slade took second place in the PHRF 1 class in 2011 with his Santa Cruz 52 Renegade and marks this year as his fifth Pineapple Cup. “It’s got to be one of the best ocean races in the world. Not only is it challenging but also the scenery is just unbelievable, and when you get to Jamaica, it’s like no other place. This race always has a very impressive fleet with a lot of great boats. We are going to try to sail well again this year, but more importantly, have fun.”

Event rookie, but veteran in the world of ocean racing, Michael Hennessy will also be competing in his Class40 Dragon. “We’d like to be competitive, have a lot fun and enjoy a new course with new surroundings,” said Hennessy, who already has an impressive resume when it comes to offshore sailing, including racing double handed aboard Dragon in the Transatlantic Race 2011.

This year, Hennessy will be sailing with a team of five. “We’re looking forward to matching up against the other Class40 (MacKenzie Davis’ AMHAS) and racing handicap against the rest of the fleet,” said Hennessy. “Our boat is pretty well dialed in right now and moving fast.”

President of the USMMA Sailing Foundation, Ralf Steiz, sailed onboard the Pineapple Cup’s IRC Class winner Genuine Risk in 2011 and will be returning again this year with a new program, All American Ocean Racing, which prepares sailors, age 30 and under, for offshore racing. The team, which will be sailing the IRC 52 IceFire, hopes to race in the Volvo Ocean Race 2014-2015 and includes Mark Towill, Charlie Enright, Chris Welch, Chris Branning and Jesse Fielding.

The largest boat in the IRC Class is Jim Muldoon’s new Andrews 80 Donnybrook. “This boat is definitely a racing boat,” said Muldoon who has raced in the event six times in the past on his other boats of the same name and this year will have 18 crew members onboard during the distance race. “Donnybrook is bigger than any of my other boats; it has a canting keel and is very racing oriented.”

His most matched competitor is George Sakellaris with his 72ft mini maxi Shockwave, which came off a great year in 2012, winning its class at the Newport Bermuda Race, the NYYC 158th Annual Regatta presented by Rolex and the Sperry Top-Sider Charleston Race Week. “They will be a true competitor for us,” said Muldoon.

The Pineapple Cup – Montego Bay Race presented by Appleton Estate Jamaica Rum is endorsed by the Jamaican Tourist Board and managed by the SORC. Sponsors include the Montego Bay Yacht Club, Storm Trysail Club, and Lauderdale Yacht Club. Immediately after the start the racers cross the Gulf Stream for the Northwest Providence Channel. The middle of the race usually offers a fetch down the eastern side of the Bahamas Island Chain towards the tip of Cuba. The final stretch is a sailor’s dream: a 240 mile downwind sleigh ride from Cuba’s eastern tip known as Windward Passage to the finish at Montego Bay. At the finish, sailors are treated to a week of fun with cocktail parties every night, steel bands, limbo dancing and other fun displays and competitions, ending with a superb dinner and dance along with a prize giving ceremony on Friday, 15 February.