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A Q&A with Chris Woolsey, regatta chair of the Miami to Havana Race

by David Schmidt, Sail-World USA Editor on 13 Mar 2017
Miami to Havana Race Marco Oquendo/SORC
One of the coolest aspects of distance racing is the opportunity to wend between scenic islands and around geographic features, ideally ending in a welcoming locale for the finish, the after-party, and the opportunity to see new places and meet new friends. And if one happens to live in the Sunshine State, one island in particular holds a magnetic force on sailor’s imaginations, fed both by dreams of kind souls, beautiful beaches and organic living, as well as that universal attraction towards things that were once illegal but have now turned the corner.

On December 17, 2014, then-President of the United States, Barack Hussein Obama, dropped these now famous words, ushering-out a half-century-plus of ugly relations with our island-nation neighbor, and ushering-in a new era of cross-border openness. “Good afternoon,” said President Obama. “Today, the United States of America is changing its relationship with the people of Cuba.”

While this could change with a stroke of #45’s often-reckless pen, sailors immediately heard the siren’s call to start racing to Cuba, and in 2016 the Miami to Havana Race, hosted by the Coral Reef Yacht Club and Hemingway International Yacht Club of Cuba, with the Southern Ocean Racing Conference (SORC) serving as the event’s official Race Committee, was born.

For anyone who is just tuning into the concept of distance racing to Cuba, the history is rich. The first St. Petersburg to Havana Race unfurled in 1930 and this race, as well as others, was going strong until the curtain dropped on U.S.-Cuban relations in 1959. Flash forward 57-odd years and the inaugural Miami to Havana Race took place February 10, 2016, attracting a wide range of boats and sailors.

The 2017 race is set to start on March 15 and is certain to hold adventure-both sailing-related and cultural-for the sailors lucky enough to be participating in this historical-and for now legal-race. I caught up with Chris Woolsey, regatta chair of the Miami to Havana Race and SORC race chairman, to learn more about the this exciting race.

How are your entry number looking this year, compared to previous years?
Last year was the Inaugural Race, so there was maximum interest in the event. Many potential competitors were on the fence and wanted to play it safe by staying home, but we still ended up with 46 [starting boats]. We are down a bit this year, with only 37 boats. That is due to two main factors, I think.

First, we moved the race from early February to March out of respect for the Pineapple Cup Montego Bay Race, which has always held that early February time slot, in odd-numbered years. We did not want to hold our race in conflict with the Pineapple Cup. The problem is that by mid March, many potential boats and more potential skilled crew are in the Caribbean for their racing season.

Another issue is that we did not get support from the West Florida boats this year, who naturally were drawn to the St. Petersburg to Habana Race. You cannot fight history, and that was nothing short of a historic return of a classic race. That was evident in all of our SORC races this year, the Nassau Cup Race, the Fort Lauderdale to Key West Race, and the Havana Race. Our races have always had a significant West Coast [of Florida] presence, which we appreciate, but that was way down this year.

I note with some concern that we had a general downward trend in participation in all of our races this year. That happens from time to time. We can speculate as to the reasons being electoral/economic uncertainty, schedule conflicts, or any number of things, but I tend to believe that we just need to do a better job getting the word out about what our events have to offer.

Our formula is simple: fun, challenging races, to interesting locations, with fun parties on either end of the race course, for as little money as possible. We will be pushing that message much harder after Havana this year.

How competitive do you think this year’s race will be?
I think that this race is always going to be very competitive, with any number of boats being in the mix. I will expound on this a bit more in [later in the interview], but the reason for this is that the course requires competitors to leave all of the marks of the Florida Keys to starboard, meaning that they can head across the Gulfstream whenever they see fit.

That puts a heavy burden on navigators, strategists and even weather forecasters (hat tip to our Official Weather Sponsor Weather Routing Inc, WRI) to make a decision on when to cross.

Some will get it right, some won't, but there is no way of knowing who will get it right in any given year. The viewing on the Kattack tracker will always be very entertaining because of this. More on that in a bit.

What aspects of the 2016 race were best loved by the sailors?
The absolute best part of this race, and any other Havana race, hands down, will always be the Cuban people and the welcome we receive from our hosts at Club Nautico Internacional Hemingway. Competitors can look forward to meeting sweet, friendly, beautiful people at every turn.

The experience is very much akin to when we were kids and finally met that person in the neighborhood to whom we never ever spoke, only to find out that they were among the nicer people in the neighborhood. Our neighbors to the south are by far the best part of this event.

Is the race introducing any new elements, classes or social events to the calendar this year?
Yes, after getting inquiries and entries from a number of cruisers about last year’s race, we decided to try to accommodate them with their own class in this year's race. The class is an Assigned Rating Class, with ratings handled by the East Coast Racer Cruiser Association.

It is the biggest class in the race, and I think (and hope) that this may be the sign of an opportunity to bring some boats onto the racecourse [that] we do not often see, because we at [the] SORC have some interesting places to take them....

How would you describe the Miami to Havana Race, compared to some of the other distance races that end in Cuba? Or, in other words, does your event attract different kinds of sailors, and, if so, can you explain?
I am always reluctant to say anything negative about anyone's effort to encourage more people to engage in the sport of offshore sailing or seeing Cuba with one's own eyes. I know exactly how hard it is to put one of these events together, and will not say anything bad about any race to Cuba. My thoughts on that mirror [the] SORC’s policy and our mission, which is to build participation in the sport.

That said, if I were choosing a race it would be our race, for purely competitive reasons. The more permissive course allows more choices about crossing the Gulfstream, putting a hero-or-zero burden on navigators and strategists to make a call from which there will be no hiding for upwards of 90 miles.

When contemplating how to handle the course, I thought back to being a kid in Fort Lauderdale, and the epic races we sailed over to Bimini, southeast of Lauderdale as the crow flies. There would be a 'right place to cross' every year, and a number of wrong ones, and they were never ever in the same place from one year to the next, due to the breeze and the Gulfstream.

The one constant from year to year was the very divergent opinions about where the 'right place' was. Last year, I looked at the tracker after the first night and just laughed. There were boats spread from west to east across the screen in what had to be about a 100-mile spread. There were lots of opinions on the 'right way', but the one that was right belonged to the team on Michael Hennessey's Class 40 Dragon, in one of the few times I can recall (if ever) that a Class 40 lit-up a PHRF Fleet on corrected time.

I pondered sending the fleet down around the curve of the Keys to the Key West Sea Buoy and around that [mark] before finishing in Havana, but we do that same course with a right turn at the Key West Sea Buoy in January of each year. That course in the Ft. Lauderdale to Key West Race, which I call the Get-To-Sloppy-Joes-Before-They-Close-Race is not without its own challenges and strategies, but the tactical challenges of the Miami to Havana Race set it apart from the others, I think.

Miami to Havana is also the final race of the SORC Islands in the Stream Series, which includes the Nassau Cup Race (Miami to Nassau) and the Fort Lauderdale to Key West Race, as well as the Wirth M. Munroe Invitational Miami to Palm Beach Race, [which] is managed by the Storm Trysail Club [and which] adds an extra impetus for doing the Miami to Havana Race.

Given the current political climate in the States, are you or the other event organizers at all concerned about the race’s sustainability for future years?
I would be a fool not to be. Anything can happen. Ask anyone who has lost a loved one too early about making the most of opportunities as they arise. Nothing is forever; go and go now (and if we can go again next year, I urge you to go again next year, in the Miami to Havana Race!)

Anything else that you’d like to add about this year’s event, for the record?
Just to thank you for the opportunity to speak about two topics about which I am passionate: offshore sailboat racing in South Florida and re-establishing bonds with our neighbors in Cuba, from whom I grew up about a hundred miles and a world away.

Both are absolute treasures, and I want to welcome as many people who feel cold and boxed-in during the winter to venture south and see what we have to offer, with Nassau in November, Palm Beach in December, Key West in January, and Havana again next February. We play among those famous Islands in the Stream and we want to take you with us!

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