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 February 8, just outside Fort Lauderdale, Florida’s Port Everglades, 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 (Lighthouse Point, Fla.), 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 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 (Ponte Vedra, Fla.) 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 (Mystic, Conn.) will also be competing in his Class 40 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 Class 40 (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.”
The president of the USMMA Sailing Foundation, Ralf Steiz (Kings Point, N.Y.), 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 (Washington D.C.) 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 (Framingham, Mass.) with his 72-foot 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, February 15.
For more information, visit http://www.montegobayrace.com/

Dockside Ambiance in 2005 (Photo Credit Evelyn Harrington)
2013 Pineapple Cup – Montego Bay Race
Current Entries
——————————————————————————–
Sail Number Yacht Name Owner’s Name Home Port Yacht Type Length
——————————————————————————–
1. USA 39 AMHAS MacKenzie Davis Mill Valley, CA, USA Class 40 40
2. USA 1253 Catapult Marc Glimcher New York, NY, USA Ker 40 40
3. USA 84001 Decision Stephen Murray New Orleans, LA, USA HPR Carkeek 40 40
4. USA 66 Donnybrook James Muldoon Washington, DC, USA Andrews 80 80
5. USA 54 Dragon Michael Hennessy New York, NY, USA Class 40 40
6. USA 60292 Icefire Ralf Steitz USMMA Kings Point, NY, USA IRC 52 52
7. USA 52152 Lucky Bryon Ehrhart Chicago, IL, USA TP 52 58
8. USA 145 Rebecca Glenn Gault League City, TX, USA J 120 40
9. USA 52422 Renegade Tom Slade Ponte Vedra, FL, USA Santa Cruz 52 52
10. USA 60272 Shockwave George Sakellaris Framingham, MA, USA Mini Maxi 72
With three races conducted in strong winds, there was opportunity for boats to make a significant move in the standings on the second day of Quantum Key West 2012. Or in some cases it was a chance to further increase leads taken on Day 1. Pisces fit into the former category, moving into the overall lead in Melges 32 class by winning two of three races on Tuesday. Skipper Benjamin Schwartz and company showed superb boat speed and made some sound tactical decisions and now lead the 19-boat fleet by tiebreaker over John Kilroy and the Samba Pa Ti team. “We are a new program so it is a tremendous feeling to be doing well in a big-time regatta like Key West. Hopefully, we can keep it going,” said Schwartz, who joined the class last summer and promptly placed fourth at U.S. Nationals. Schwartz has America’s Cup veteran Ed Baird calling tactics and Quantum professional Scott Nixon trimming the jib and spinnaker. “You have to give Ed and Scott a lot of credit for getting our boat up to speed,” he said. “I’m fortunate to have a great crew. Today was very challenging because the wind velocity was up and down and the sea state was not very forgiving, but the guys never stopped working and we were able to change gears pretty well.” Race committees on all three courses completed three races in 8-14 knot easterly winds.
With five races in the bag, organizers with Premiere Racing are already halfway to the stated goal of holding 10 races during the five-day regatta. There was a lead change in the Farr 40 class as well with Charisma (Nico Poons, Monaco) and Struntje Light (Wolfgang Schaefer, Germany) overtaking Groovederci (John Demourkas, Santa Barbara, Cal.). Struntje Light has posted a pair of seconds and finished no lower than fourth in the seven-boat fleet, but Charisma holds the overall lead via tiebreaker by virtue of winning Race 5. “We had a very good day on the water and are happy with where we stand at the moment,” Schaefer said. “We have nice boat speed upwind and our crew work has been excellent. We have a very good tactician and he’s made some fantastic calls that have kept me in phase.” Renowned Italian professional and America’s Cup veteran Vasco Vascotta is calling tactics aboard Struntje Light, which has competed in Farr 40 class at Key West ever since 2002 with a top finish of third. “Wolfgang is doing a good job of driving and is getting better every day. The guys onboard have a great attitude and are ready to fight to the end. The good news is that we can still improve our performance.” PowerPlay lived up to its name by making a strong move in IRC 2 class with a strong line of 1-3-4 on Tuesday. Owner Peter Cunningham, a resident of Georgetown in the Cayman Islands, has a nice mix of amateur and professional crew with tactician Tony Rey, trimmer Dave Scott and bowman Geordie Shaver among the superstars aboard. “We’ve only had the boat for six months and we’ve made a lot of modifications during that time,” Cunningham said. “We’re pretty happy with our performance so far. We’re sailing fairly well and having a lot of fun.” Quantum Racing, skippered by Doug DeVos, continues to set the pace in the 52-foot class and leads PowerPlay by six points. Terry Hutchinson, helmsman for the Swedish syndicate Artemis Racing that is Challenge of Record for the America’s Cup, has made strong tactical calls in leading Quantum to victory in three races and second in the two others. “Today was far from straightforward. The wind was very shifty and there are some tricky current patches to deal with,” Hutchinson said. In other classes, the three-race day merely served as an opportunity for the early leaders to extend on the competition.

Red (Copyright 2012 Ingrid Abery)
Ran, a Judel-Vrolijk 72-footer, continues to sail impressively in the Mini Maxi class (IRC 1), winning all five races so far. Red, skippered by Joe Woods of Great Britain with Paul Goodison aboard as tactician, has accomplished the same feat in the inaugural Farr 400 class. “I guess we’ve just figured the boat out a little faster than the other teams,” said Woods, who has previously sailed a Melges 32 at Key West. “We’re winning, but not by much. The racing has been awfully close.” West Marine Rigging/New England Ropes has posted straight bullets in Melges 24 class and built a commanding 10-point lead over Alan Field and the WTF team. Detroit resident Bora Gulari is steering and getting tactical advice from Australian native and North Sails pro Jeremy Wilmot as West Marine Rigging/New England Ropes seeks to follow up on its 2011 national championship. Groovederci, skippered by Deneen Demourkas of Santa Barbara, Cal., has won all five races in Farr 30 class. Teamwork, a J/122 owned by Robin Team of Lexington, N.C., has posted two bullets and a pair of seconds in grabbing a narrow one-point lead over the 1D35 Tres Hombres in PHRF 1. “We’re having a great time because the conditions have been terrific and the competition has been spectacular,” said Team, who has his brother and two sons in the crew. “We’ve been mixing it up with Tres Hombres and finished overlapped with them in the first two races today. Rush is also tough so I think it will be a dogfight the whole way.” Rush, a J/109 skippered by Bill Sweetser of Annapolis, was named Lewmar / Navtec Boat of the Day after posting a superb score line of 3-2-1. Tom Babel is calling tactics while Quantum pro Tad Hutchins is calling tactics on Rush, which is currently third in PHRF 1 and second in the J/Boats Subclass. “The conditions were very good for us today. When the wind is 14 knots or less we can fly our big jib, which is kind of like our secret weapon,” Sweetser said. “We pay for that jib in our rating so it’s good whenever we can use it.” It’s been close but no cigar for Rush at Key West as Sweetser’s boat has finished first or second in class several times, but never come away as overall winner at week’s end. “One of these years we’re going to finally break through and it’s going to be wonderful,” he said. Regatta dates are January 15 – 20, 2012.

Melges 32 Copyright 2012 Tim Wilkes
For more Key West Race Week photos by Tim Wilkes check out Tim Wilkes Photography
















