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2011 Race Coverage:

Event News:

February 12, 2011
The Pineapple Cup Race Committee has awarded Hugo Stenbeck and the USMMA crew of the 97’ canting keel super maxi Genuine Risk the 2011 Pineapple Cup trophy for the best performance by a monohull boat.

Photograph provided by William E.

George David’s Rambler 100 took line honors for the 2011 Pineapple Cup Race with an elapsed time of just under 3 days and 2 hours, but Genuine Risk finished close behind to win the Silver Seahorse trophy for first place corrected time in IRC Division. 

James Muldoon’s venerable Santa Cruz 72’ Donnybrook won the PHRF Division and was awarded the Arawak Perpetual trophy for first place corrected time in the PHRF Division.

Photograph provided by William E.

Major awards presented by the Montego Bay Yacht Club at the prize giving ceremony on Friday evening were:

For 1st monohull boat to finish.
Presented to Rambler 100 – Skipper George David

For 1st overall IRC rated boat.
Presented to Genuine Risk – Skipper Hugo Stenbeck / USMMA

For 1st overall PHRF rated boat.
Presented to Donnybrook – Skipper James Muldoon

For 1st overall IRC & PHRF navigators.
Co-Presented to:   Genuine Risk Navigator –  Peter Tans
Donnybrook Navigator – Kurt Lowman

For Best overall performance by a monohull boat.
Presented to Genuine Risk – Skipper Hugo Stenbeck / USMMA

February 10, 2011
Instant Replay
Check out the race replay by Kattack showing a replay of the tracking over the course of the race. This is an awesome feature of the Kattack software.  See where gains and losses occurred. 

There is one problem with the current replay software.  The Lat/Lon conversions get a bit wonkie and boats sail through islands.  Kattack is working on a permanent fix – in the mean time here is a quick work-around:

  • Go to “Follow Boat” on the  top right and select any one of the boats
    (just not “All Boats”)
  • Check ON "Map” (you want to see Islands – right?)
  • Check OFF “Auto Camera” (this is the auto zoom that is the problem)
  • Speed up to 200x max (optional but suggested)
  • Now you can zoom in and out manually as you follow the class and all the boats.
  • Click and drag the triangle at the bottom to fast forward and reverse.  See the whole race in 60 seconds!


Photo provided by William E.

February 8, 2011
Rambler 100 Takes Line Honors
Rambler 100 crossed the line and received her customary case of Red Stripe at 14:53:52 Tuesday evening with an elapsed time of 3 days, 1 hour, 48 minutes and 52 seconds.  While not a race record, the elapsed time was particularly impressive given the benign conditions throughout most of the course.  Finishing right on her heals was Genuine Risk after making gains during the final day between Cuba and Jamaica. Live race results are posted as the rest of the fleet finishes.


Photo courtesy of William E.

February 7, 2011
Start Photos
Here is a gallery of start photos captured by William E. More start photos will soon be available at as well.


Photo Courtesy of

February 5, 2011
Jamaica Bound!
We had two great all-clear starts, both of which were very punchy. The PHRF class was actually a bit closer to the line than the IRC class, with a minute to go, but both were right on the line at the gun. Sjambok wanted the boat and got it, front row start with speed. Very nicely done, followed by a fight with Bella... Pita, second row at the boat. Rambler 100, Ken Read at the helm, did a very nice job of locking the fleet into the upper 2/3 of the line, and then put the bow down and rumble rumble rumbled to a leeward end start with speed and a LOT of room to themselves.

The PHRF class saw Musica, the Aerodyne 38, right at the boat, front row, with almost full speed, with Different Drummer to leeward. The whole class bunched into the top half of the line in a very tight pack. Good action, four or five rows deep.

Check out the race tracking and race coverage for more information, including some videos at the start of both the IRC class and the PHRF class.


Skippers Meeting Photos
Here's some photos from the skipper's meeting last night by William E. Check back later today for start photos as well.


January 10, 2011
Official Race Apparel
Get your official apparel for the 2011 Pineapple Cup -Montego Bay Race. Visit our online apparel store to order. Custom monogramming is also available. Order Now.


December 26, 2010
Records are Made to be Broken
Paige Brooks, SORC PR -
The Pineapple Cup raced on odd years from Fort Lauderdale to Montego Bay has a current standing record from the 2005 running of the 811nm race by Tom Hill's Titan 12 of 2 days, 10 hours, 24 minutes and 42 seconds.  If the conditions are even close to those of 2005, early entries Rambler, Beau Geste, Bella Pita and Donnybrook are certainly up for breaking this record, called the Windward Passage Challenge which stood for 30 years until 2003 when it was broken by Zephyrus V and again in 05 by Titan 12.  


Overall winner Privateer

2009 Pineapple Winner "Privateer"


Montego Bay Red Stripe Tradition

The Pineapple Cup Tradition Continues
The cases of Red Stripe are chilled, the bar is stacked with rum. The Race Committee hands a welcome case of cold Red Stripe to the crew of every finishing boat as soon as they cross the line.  The Pineapple Cup Trophy (seen in photo) is waiting to be claimed by her new owner.


Jamaica Yachting Association
Jamaica Yachting Association

Lauderdale Yacht Club
Lauderdale Yacht Club

Montego Bay Yacht Club
Montego Bay Yacht Club

Storm Trysail Club
Storm Trysail Club


Pineapple Cup - Montego Bay Race 2015
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