32nd Biennial Pineapple Cup – Montego Bay Race Class 40s and Others “In for a Blast”

Set to begin Friday, February 6, the 32nd edition of the venerable Pineapple Cup – Montego Bay Race will start in Port Everglades, Florida, and send its 12-boat fleet on a challenging 811 nautical mile course to Montego Bay, Jamaica. George Sakellaris’s (Framingham, Mass.) 72-foot Shockwave will be the largest boat competing, so it should be interesting to compare her results with those turned in by the balance of a fleet comprised primarily of 40 footers.

Quite convincingly at the 2013 “MoBay,” Shockwave won both overall honors and her IRC division after finishing just 58 minutes short of the elapsed time record (two days, 10 hours and 24 minutes, set in 2005 by Titan 12). It is anyone’s guess, however, as to what this year’s conditions will bring and whether they will favor new talents or veteran teams.

(Left) Shockwave’s Reggie Cole accepts the top prize for the Pineapple Cup – Montego Bay Race in 2013. (Photo Credit sukimacphoto.com);
(Right) At the 2015 event, Shockwave will be the largest boat competing. (Photo Credit Boatpix.com)

“You can expect every point of sail during the race,” said Principal Race Officer Chris Woolsey, “and I always advise teams to save their spinnakers for the last legs, since in some conditions this race can be a war of attrition.”

That was the case in 2013, when Michael Hennessey’s Class 40 Dragon had the misfortune of losing both of its “kites” off the coast of Cuba, forcing it to limp the last 300 miles to the downwind finish. Hennessey has entered again with the same boat, which he said “loves the typical reaching and running conditions of the MoBay race.” Using boxing terms, he embellished: “We tend to be able to punch above our weight in those conditions.”

Chart of the “MoBay” race course.

Hennessey, like three others of the five Class 40s competing, will sail double-handed this year rather than with a full five-person crew like he had last time. His team will be scored against the other Class 40s as one-design and additionally under a PHRF handicap to determine the overall outcome in that division, which will be racing for the Silver Seahorse Perpetual Trophy. There is also a division for IRC, which will be racing for the Pineapple Cup Trophy. (The Silver Rose Bowl Perpetual Trophy is presented to the first monohull boat to finish.)

“If I think about all the great distance races out there, whether it’s Newport to Bermuda, Rolex Fastnet or Middle Sea, they all have something that makes them unique and interesting,” said Hennessey. “In this case, it’s special to be racing in warm conditions in the middle of February, with beautiful long stretches of reaching and running where you can let the boat cut loose. Then you arrive, and the Montego Bay Yacht Club provides the best hospitality – with great warmth and friendliness – of any race I’ve ever participated in.”

In 2013, Elizabeth Shaw (Halifax, Nova Scotia, Canada) was participating in a development program at Oakcliff Sailing in Oyster Bay, N.Y. Now, two years later, she is worthy of competing in the MoBay race with accomplished shorthanded New Jersey sailor Jeffrey MacFarland (also an Oakcliff graduate) aboard the Class 40 Oakcliff Racing Bodacious Dream.

“I am acutely aware of what an opportunity this is for me; You don’t get to just jump into a role like this,” said the 30-year-old Shaw, adding that Oakcliff only recently acquired the Class 40 as part of its fleet and made it possible for the duo to enter. As for sailing with only one other over such a long period of time (an estimated three to four days), she added: One of the most interesting things about shorthanded sailing is learning when to take your rest, how to take care of each other, getting into a groove that’s working, and making sure there’s enough energy in the tank for emergencies and good decision making. It’s always a physical and mental challenge.”

Jamaican Entry
With entries hailing from as far away as Michigan and California, none will be more supported by well-wishers than the one representing Jamaica itself. Sailing in IRC division, the J/120 Miss Jamaica will have aboard it Montego Bay Yacht Club Commodore Nigel Knowles and his 16-year-old daughter Zoe Knowles, who is Youth Commodore for the club. “It felt only right to have our own team compete in a race that we run (in partnership with Storm Trysail Club and Lauderdale Yacht Club),” said the elder Knowles, “and the breaking news now is that we have the youngest-ever participant aboard as well.”

Knowles said his team will arrive in Fort Lauderdale February third for two days of training before the start. “It will be a fairly steep learning curve; we’ve mostly never sailed together as a group but one of us (Jim Wilson) has sailed on an identical boat, and we are all very active in a smaller version of the boat, the J/22, which we sail every two weeks at Montego Bay and Kingston.”

Knowles looks forward to going head-to-head with one other J/120 signed up (Tampa Girl); however, that boat is signed up to be scored under PHRF while Miss Jamaica is sailing IRC. The J/120s are 40 feet long.

JetBlue is the Official Airline of the “MoBay” race, offering 1.5 hour flights
from Ft. Lauderdale, Fla. to Montego Bay, Jamaica.

“The Pineapple Cup-Montego Bay Race has a special place in the hearts of sailors,” said Race Coordinator Evelyn Harrington, ”both for the unique challenges of its course and for the warm Jamaican hospitality waiting at the finish.” Harrington explained that every boat has a local host – “somebody to be a familiar face in a strange place” – and sailors are treated to a week of fun that includes parties and events with a local flare and a final dinner, dance and prize giving ceremony on Friday, February 13. “And now that we are part of something bigger – the Atlantic Ocean Racing Series – we have a great chance to showcase our race on the world stage.”

The Pineapple Cup – Montego Bay Race is endorsed by the Jamaican Tourist Board and managed by the SORC. JetBlue is the Official Airline of the race and sponsors include the Montego Bay Yacht Club, Storm Trysail Club, and Lauderdale Yacht Club along with Appleton Estate Rum and SelectBrands. Immediately after the start, racers cross the Gulf Stream for the Northwest Providence Channel. The middle of the race offers a fetch down the eastern side of the Bahamas Island Chain toward the tip of Cuba. The final stretch is typically a sailor’s dream: a 240-mile downwind sleigh ride from Cuba’s eastern tip, known as the Windward Passage, to the finish at Montego Bay.

2015 Pineapple Cup – Montego Bay Race

IRC
Hot Ticket, King 40, Jim Hightower, Temple, Texas
Miss Jamaica/Team Easy Skanking, J/120, Richard Hamilton, Montego Bay, Jamaica
Miss Maris, J/122, Mark Jordan, Mount Pleasant, SC
Shockwave, Maxi 72, George Sakellaris Framingham, Mass.

PHRF 1
Senara, Farr 395, Jim Eamonn/Bill deLisser, Miami, Fla.
Tampa Girl, J/120, William Terry, Tampa, Fla.
Vortices, J/145, Chris Saxton, Plymouth, Mich.

Class 40
AMHAS, Class 40, Davis MacKenzie, Mill Valley, Calif.
Dragon, Class 40, Michael Hennessy, New York, N.Y.
First Light, Class 40, FK Day, Chicago, Ill.
Oakcliff Racing/Bodacious Dream, Class 40, Jeffrey MacFarland, Oyster Bay, N.Y.
Pleiad Racing, Class 40, Edward Cesare, Norwalk, Conn.

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