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Posts Tagged ‘pineapple cup’

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Screen Shot 2017-02-03 at 1.54.26 PMWhile the 2017 Pineapple Cup once again sees a tiny fleet taking the start line in just a few minutes’ time, we’re happy to see the race happening for another year.  It’s the ultimate Western Hemisphere big boat race course, and it always provides great stories for the competitors and for those of us stuck on dry land.  Here’s a pre-race report from Michael Hennessey aboard the Class 40 Dragon.  Pre-race photo gallery at the event Facebook Page and track the fleet here.

It looks like a classic.  Forecast is for us to start out in relatively light easterlies, with a shift to the NE with a bit more pressure coming over night.  That sets up a tactical beat from the start out over the top of Great Isaac, one of mny Bahamian islands we will be passing by over the next couple of days.  The key will be how far to push the first beat to the NE.  With that impending shift coming, you risk overstanding and giving up precious miles to the competition. At the same time, you want to use the Gulf Stream while you have it in order to get North.

This first leg is tactically important because whom ever makes it to the Northeast corner of Eluthera first gets the chance to turn down into the reach that will be the eastern side of the Bahamas.  The forecast is to build, maybe into the low twenties, and it is going to be a fast ride so those who get there first will leg out on the fleet.  This middle third of the race is also a parade… no passing lanes, no strategy, just pedal down speed.  The best you can hope for is to get there first.

Then through the windward passage between Cuba and Haiti and you turn further downwind towards Montego Bay.  This last third is all about the VMG running, surfing wave after wave.  Strategy comes back into play with the decisions about which lane to take across the Caribbean, and when / where to make your gybes.  It is champagne sailing when the conditions are right, and at the moment they look oh, so right!

The fleet may look a bit small with 11 boats, but there is some great hardware in this year’s edition.  We are going to be benchmarking ourselves against the other Class40, Amhas with the added challenge that they are fully crewed with some impressive talent and I chose to go doublehanded with the even more impressive Kyle Hubley as my co-skipper.  We think we are up to the challenge.  And we also hope to handicap out well against the other boats.

This is my third time doing this race and I keep coming back because the course has the promise of so much awesome sailing, and the reception at Montego Bay is unrivaled in its hospitality.  I am looking forward to getting there and drinking down some of that cold Red Stripe!

February 3rd, 2017 by admin

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Michael Hennessey and Tristan Mouligne hit up the the irie-est race in the world aboard the Class 40 Dragon.  Results here, and more info on the Pineapple Cup/Mo Bay Race on the SORC Facebook Page. Nigel Lord Photo.

Here I sit on the beach of the Secrets resort next door to the Mo Bay Yacht Club, watching my boat sail off across the horizon towards the western tip of Cuba,  musing what marketing genius thought it was a smart idea to call a resort “Secrets”.  Is there really that big a market for illicit affairs that they need 800 rooms and a full resort for them?   Or does ‘Secrets’ refer to the secrets that couples keep from one another; things like, “I’d rather be on that boat, eating freeze dried pasta and shitting in a bucket, than sitting on this white-sand beach?”

It really is a nice resort.  A collection of buildings, pools and beach that is hermetically walled off from the real Jamaica by concrete, iron, and security guards.  Plush rooms, plush towels, plush seat cushions.  The days seem to be centered around the tidal movement of people from food to beach to bar to food to pool to food.  Its a lot like what I would imagine a very nice cruise ship to be, but with trees, no kids, and apparently, lots of Secrets.  And I’d rather be on the boat.

Delivery crew Dan Valoppi and Kyle Hubley flew in yesterday and shoved off this morning, delivering Dragon back to Charleston.  A good number of boats departed yesterday, Oakcliff bound for Antigua and the C600, then Amhas and Miss Maris for Charleston.  Dragon will likely catch Miss Maris tonight, and then everyone will end up tied up in Lauderdale around Tuesday as they sit out a low that is going to fill in south of Hattarras.  Other than the stopover, it looks like a run down the Caribbean, a short motor off Key West as the wind flips around and then a reach up the Keys.  It’s delivery mode, so they have books and music and long naps to look forward to.

This was my second time sailing the Pineapple Cup/Jamaica Race, and it is still my favorite race.  The course is unique and just long enough to feel like an ocean race. The vibe is low-key fun, warm hospitality and a welcome relief from the cold that has the Northern climes’ balls in its icy grip.  We woke up on race day knowing that it was going to be an ‘athletic’ start, with most of us holding off our departure from under the bridge to spend as little time as possible being whipped around in the pre-start.  We already had our main loaded and our trinquette (staysail) plugged in before leaving the dock, so it was a fairly simple matter of slapping our way out of the breakwater and getting far enough the beach to know what the wind conditions really were all about for the first part of the race.

Which was a very, very shy reach.  Or rather, close hauled and fetching on port tack (ok, 55 degrees TWA in 25-30) with two full tanks of water ballast.  The start was uneventful for us, not so much for a few others that had some issues getting their headsails under control.  But the rust was showing, and it took us a good 2 or 3 hours of tweaking before we really got the boat moving close to its polars.  In that time, we fought off Oakcliff but let Amhas pick up a couple of miles on us.  The sea state coming across the Gulf Stream was a mess, with short steep waves coming from almost every direction until we got across.

Screen Shot 2015-02-18 at 9.11.39 AMOur bigger mistake was footing off a bit too much, ending up South of our first mark, Great Isaac.  So when we got there around midnight, we ended up having to put a 3 mile tack to the north – something none of our competition had to do.  Silly, stupid mistake on our part, followed by a much bigger one when I accidently auto-tacked the boat, and in doing so, dropped the bagged A2 in the water. Those bad boys get massively heavy when they get wet, and I still have the bruises from the lifelines where I leaned against them to get the kite back on the boat.   Then, proving that I am much less smart than I think I am, I managed to auto tack the pilot again an hour later.

Those three mistakes set the table for our entire race – a bummer, because we really didn’t make any more for the remaining 800-odd miles.  But the first three mistakes put us behind Amhas by a good 15-20 miles, with the wind clocking the entire time. Once we got past Issac we were able to put a bit more South in, and then more once we got past Stirrup, but the entire time the wind kept clocking forward which kept us on the wind and going slow.   Meanwhile, the boats in front of us were able to get a little bit of cracked off sailing across the top of the Bahamas, and then once they got past Eleuthra, onto a full-on blast reach for five hours while we were still tight on the wind – translating into a 30 mile lead by the time we were able to crack off.   And when we got to the corner on Saturday night, the wind had already clocked forward, so while we got a reach, they’d had a broad reach.   It was a rich-get-richer story, most notably for the near record-setting Shockwave, but also for Amhas, Renegade, Vortices, and Oakcliff.

Down the east side of the Bahamas, it was a decent reach but never far enough back to get a code sail up.  The wind settled a bit at 18 to 25 and as a result it was a very wet ride, by the light of a giant moon that had just started to wane.  By Sunday morning we were down to the bottom of Cat Island – we chose to take it to the outside – then we had more wet, fun near-reaching through Sunday and into Sunday night.  Demonstrating how much better that point of sail is for high-stability Class 40s compared to conventional boats, we managed to erase a 15-mile lead that SC52 Renegade and J/145 Vortices had and pull in front of them by early on Monday morning.  This was as we approached Cuba, and judging from the thundercells building in the moonlight, we knew we were going to get plastered.  Nighttime cells in the Caribbean are always interesting; with too much wind on the edges and no wind in the middle and all of it shifting over 360 degrees.

That, however, was not really the bad news – which, instead, was a big shift on the other side.  We managed to get enough breeze to pull us within 2 miles of the eastern tip of Cuba by 7 am, but then the breeze shut off for 3 hours before it filled in from south west.  Seriously… we had been upwind for 550 miles only to literally reach the part of the course were we would make a 90 plus degree turn to the west and we end up with a wind shift that put the wind blowing straight out of our destination. Meh.

The tracker showed Amhas and Oakcliff as having gone South into the Caribbean, and the forecast called for less breeze down there. We were going to get no leverage out of following them, so we decided to rock hop down the Cuban coast.  In the end, they got about the same pressure that we got, and the tactic did not yield any meaningful results for us, but we did get to have a full day of sailing along one of the most beautiful coasts I have ever seen.  Well worth the price of admission, and something that maybe a lot more Americans will be able to see soon.  Throughout Monday, we continued to play tacking games with Vortices, the one boat that followed our lead down the coast.  Not surprising for a J145, they pointed a hell of a lot better than us and gradually legged it out in front of us.

Monday night gave us a chance to get to know our American servicemen as we ended up within two miles of the base at Guantanamo Bay.  The boys at Gitmo were unamused at our proximity to their exclusion zone, and they let us know via in no uncertain terms via VHF.  I suspect that had it been daylight, they probably would have paid us a personal visit.

Tuesday morning saw the sun rise behind clouds, and saw the breeze clock back to the East, freeing us to finally make some better VMC towards Montego Bay.  That continued to midday, when we had the front move through, the sky clear and the wind shift back to the WSW.  Yet another solent reach, and we started to chip away at the 14-mile lead that Vortices had built on us.  We caught one last tack to the West and then banged the layline from 80 miles out.  In an effort to keep up boat speed, Vortices footed off to below the finish line, while we were still making a knot on them, drag racing to the finish.  We thought for sure that we had them when they got to the beach a mile or so east of the finish line, but somehow they got lifted at the same time they went into some magical high point mode and they just pipped us at the line.

After a short motor to the dock (did I mention, free dockage?), we were met by our host family carrying a bucket of ice cold Red Stripe…at 3 Am in the morning.  I think it is that moment that best shows what this race is all about.  Jamaica is one of the most hospitable places anywhere in the world, and the members of the Montego Bay Yacht Club may be the best of all.  The restaurant stays open all night as boats arrive, every boat gets a host family that helps out with anything that might be needed, the members staff all the finish line duties, and they throw a cocktail party or dinner for the week of arrival to make sure that you have a chance to hang out and tell tall tales of your seafaring adventures.  It is the warmest, nicest bunch of people that I have had the chance to meet in sailing.

The Ocean Racing Anarchy thread on this race started out with a question about the state of this race and its relatively small size this year, and it’s a good question.  The state of big boat racing in Florida, the longsuffering economy, and the RORC C600 have all conspired to pull a number of boats away from the bi-annual Jamaica Race.  Couple that with – let’s face it – a weak marketing and communication effort over the past few years, and what you have is a decent little fleet – but not what it could or should be.

The reality is that the eastern Caribbean winter circuit is very enticing, but it is also a huge commitment of time and money.  In the meantime, the (hopefully) imminent opening of Cuba should create an opportunity to  build a mid-Caribbean circuit of three or four races that could follow Key West Race week and offer a lower cost, easier option to get winter racing in awesome waters.  I know there are some Anarchists working towards this end, and that the Montego Bay folks are keen to figure out a solution, and I look forward to seeing what they come up with.

I can confirm that the miles down here make it a lot easier to get through a cold winter, and while the Eastern Caribbean would be great, it just doesn’t fit into my schedule or budget.  But the Pineapple Cup does, and I’ll be back to do it all over again.

Until next time – Walk good and likkle more.


February 18th, 2015 by admin

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Clearly there is something wrong at the Pineapple Cup, with just 10 entrants filling this legendary race course for last week’s slide to Jamaica.  Can it be saved? Should it?  The wild success of the RORC Caribbean 600 (which starts today with a record fleet of 53 boats) argues that it can, provided the organizers put even the slightest amount of work into promoting their race – something they just didn’t bother with this time around. Meanwhile, Chris Museler is currently the world’s best sailing journalist, and we’re glad to have him as a daily reader and occasional contributor to our own site.  Here’s the New York Times and Outside Magazine writer’s take on just what makes the Pineapple Cup so spectacular.  Like video? Here’s one from Dragon’s trip.

Ocean racing is something I revisited in my life when I began freelancing in 2004/05 when I raced in the Rolex Transatlantic Race aboard an 84′ yawl from 1939. Since then I have been able to experience some amazing pieces of water around the Atlantic theater. Offshore courses were chosen for many different reasons over the decades but I would have to say that even though the location and timing is less convenient than most of the major races, the historic Pineapple Cup from Ft. Lauderdale to Montego Bay is by far the best stretch of water any sailor can race upon.

I was fortunate to sail in this race last week aboard Michael Hennessy’s Owen&Clarke Class40 Dragon. We sailed with five crew which is quite crowded for a doublehanded boat with water ballast. I won’t bore you with too many details, but first and foremost, the perfect analogy for this race is doing a never ending windsurf or kitesurf downwinder in the Gorge, or off the Molokai Channel or any other long stretch of perfect ocean you have seen from the plane: pure, perfect angle, at speed, with warm water and sunshine for as long as you feel like it.

The icing on the cake with this event is the ridiculous history you join when you participate for the first time. When the Southern Ocean Racing Conference was the king of coastal racing circuits in the 1970s and ’80s, this race became the stuff of legends. One fifth generation Jamaican told me, “A young man named Ted Turner laid on his back at the end of that dock right there, looked up at the stars and said, ‘One day we’ll be transmitting everything from up there,’” predicting an eventual communications and TV empire.

There’s more of course including the chapter of Jim Kilroy’s new book KIALOA US-1: Dare to Win about the battles between his maxi and Windward Passage when that class was the pinnacle of all yacht racing. The images of two giants rounding Guantanamo Bay with clouds of sail in the firing trade winds are what made dreams for generations of now top sailors.

Unfortunately the other winter events in the Caribbean are more than 1,000 miles upwind from Jamaica. And the rising popularity of the heavily marketed RORC 600 in Antigua and others in the Eastern Caribbean have made the Pineapple Cup fall off the radar, with 10 starters this year. If you are interested, however, in just simply sailing a perfect course in a significant part of the world (beam reach down the entire Bahamaian chain, round Cuba and slide through the Windward Passage the “right” way), than join the history of this race, it was truly the most special and enjoyable ocean race of my life. Even the small, ice-cold bottle of Red Stripe I was handed at the Montego Bay Yacht Club tasted like champagne, perfect!

February 18th, 2013 by admin

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