3 Days to the start of the 33rd Pineapple Cup - Montego Bay Race

by Julianna Barbieri on 2 Feb 2017 With three days to the start of the 33rd edition of the Pineapple Cup – Montego Bay Race, the field of eleven is readying for the 811-nautical mile race departing Miami on Friday at 2pm ET. One of the top contenders is the Mills 68 - Prospector who has their eye on Wizard as their top competition. In addition, Shawn Burke is set to compete in his 13th Pineapple Cup alongside his brother Steve who will be racing in his 14th edition of the race. And, weather models are living up to the notoriety for the race with plenty of downwind and reaching conditions forecast.

What they're saying:

Prospector's Spinnaker Trimmer Tim Keyworth, on the race and their competition:

“This will be my second Pineapple Cup. It is one of my favorite offshore races, it’s a great distance, you’re going from warm weather to warmer weather, and you land in Jamaica, not a bad way to do it!

The Montego Bay Yacht Club is fantastic. The Yacht Club stays open 24/7 from when the first boat finishes to when the last one arrives! It’s always good to have a cocktail at four in the morning! The hospitality is fantastic, just an all-around good time.

This time around we have a great boat and great crew with Wizard as our main competition. They’re a very well sailed boat with many pro’s onboard including Charlie Enright, Mark Towill, Nick Dana and Chris Larson, so they’ll be very, very competitive, but we wouldn’t be here if I didn’t think we had a shot!”

Shawn Burke, Renegade on his 13th Pineapple Cup:

“We sail with such great folks, picking who you go to sail with is part of it. In my opinion this is the greatest race course out there. You get a little bit of everything, you get some upwind work, you get some reaching work and hopefully you get the sleigh ride from windward passage to Jamaica. You don’t always get that, last time it was upwind that whole way! It’s always a surprise.

This race is always different and you can always expect something in the weather to throw a wrench in it. It’s just exciting that way – and of course the weather is great! Sailing through the Bahamas is never a bad thing! One of the greatest things for us that we have so many friends now on the island (from doing the race so many times), so we love to see them when we arrive.”

Scott Giering, Senara, on the weather forecast:

'From yesterday to today (the wind direction has) backed about eight - ten degrees and the velocity has come down a little. The estimate currently is that the Gulf Stream is on this first third of the crossing, a strong three knot for a narrow band of six miles and then tapers back really quickly. Whoever doesn’t have to tack to get around the Issacs (the first turning point of the race) will have a considerable lead.

This will be my first time back to Jamaica since I did the race back in 1992. I love the concept backing the boat up (in Jamaica) and getting a case of Red Stripe. I think that’s a classy way to finish a race!”

A complete list of registered entrants can be found here. The Biscayne Bay Yacht Club will host the Pineapple Cup Skippers Meeting and crew party on Thursday, February 2nd.

For more information, please visit website