The Heineken Regatta


Apr 11, 2017

Backstory: Five years ago Winnipeg couple Kelly Brown and Linda Strachan bought a 36’ Prowler cruiser to explore Lake of the Woods. Three years ago, they decided to run away south, took sailing lessons and purchased Silhouette, a Catalina 470.

With the help of friends from the Northern Yacht Club and the Salty Dawgs, they took the boat south to Nanny Cay Tortola and liveaboard the Catalina in the winter, the cruiser in the summer. What a deal!

This year they entered their cruiser in a relaxed division of the Heineken Regatta. Here’s their blog that describes the experience.

Kelly Brown WinsJim Fogg , Linda Strachan, Kelly Brown and Dale Kilmnick shortly after receiving the trophy Credit John Gallaugher

The Heineken Regatta (March 3-5, 2017) is the largest warm water regatta in the world. Participants from 35 countries on approximately 180 boats come to St. Maarten for this race. We’re talking professional race crews on multimillion dollar monohulls and multihulls.

This year the regatta included a cruiser’s division intended for those sailors who are cruising the islands and have cruising sailboats. The division is formally known as the Lottery Class. The idea of the Lottery Class is that there would be only 1 race per day for each of the three days, it would start later in the day and be a relatively shorter course so that races wouldn’t exceed 3 hours. Additionally, the handicaps given to each boat in the division would change on a daily basis. If you did very well on race day 1, you would get a larger handicap on day 2. If you did poorly on day 1, you’d get a better (lower) handicap on day 2. There was a winner each day, no cumulative winners.

So what exactly does this all have to do with relatively new sailors Kelly Brown and Linda Strachan who have never raced; on a liveaboard Catalina 470 boat that has never been raced?

Enter seasoned veteran racers Jim (Fogger) Fogg and Dale Kilmnik. Dale is staying on Fogger’s boat Latitude Adjustment for a couple of months. Over evening cocktails one night at the St Maarten Yacht Club, Fogger suggested that the four of us should enter the regatta on our boat, Silhouette. He would take the helm and skipper the boat, and together with Dale, they’d teach Linda and I how to race.


He told us about the massive parties and the crowds that line up along the bridge to watch the parade of boats leave and enter the lagoon each day. He shared stories of past regattas and the incredible people he’d met. I asked why he didn’t enter his boat? He said that with his inner forestay, tacking is a problem as the sail had to be furled and unfurled on each tack making it a painfully slow experience. He felt Silhouette was much better equipped for racing. Well after a couple of glasses of liquid encouragement, we agreed under the proviso that he didn’t break our house. Silhouette is our home and we wanted to keep it intact. We didn’t care if we were the first boat across the start line or the last boat across the finish line, just don’t break our boat!

We registered the next day and we were excited to attend the special party held for all the Lottery Class participants the night before racing began. It was great to see that the owners of all 11 boats in the division were all retired liveaboard cruisers with a racing history. The four of us found it interesting that all of the other boats had crews of 6-12 people. We became fast friends with the other racers and enjoyed a lot of laughs and several drinks together that night.

Friday morning was our first race. We got out in the bay early to make sure we were well prepared. Our start time was 11:00am on a race course that turned out to be 6 miles in each direction of windward-leeward. I worked the main, Dale and Linda worked the jib and Fogger gave orders as he was getting his first feel for the boat. The wind was strong. A sustained 20-knot wind with gusts up to 25.

Then 15 minutes before the start, SNAP BANG! We looked forward and the line on the boom vang snapped. All I could think of was “oh man, we haven’t even started yet and he already broke our boat”. Dale went to the foredeck and calmly told me to go grab some spectra line. It took us about 5 minutes in the pounding waves and wind to get the new line threaded into the vang and we were back in business!

With everyone back in position, we synchronized our timer with the 5-minute warning signal and Fogger began positioning us for the start. It will not come as a surprise to anyone that knows Fogger that we were the first boat across the start line, within 1 second of the race starting. Fogger yelled to the committee boat “a perfect start! Textbook baby!”. And we were off.

We got a jump on the pack as we rounded the leeward mark first at about 8 knots and headed back up into the wind. Fogger had me focused on constantly trimming the main for optimal speed, but the waves and the wind slowed us right down. We took the optimal, most direct line toward the windward mark, but we saw that a few of the boats tacked to head in toward shore, a move we felt would add a lot of time to their race as this meant they’d have a lot further to travel.

Fogger At HelmFogger at the helm of Silhouette

However it quickly became apparent that local knowledge goes a long way. We were not only getting beaten by the waves (that were just as bad for those that went closer to shore) but we were also fighting a strong current. The other boats quickly gained on us from a distance and it wasn’t long before they passed us. We rounded the windward mark 5th and made our way back downwind. With only a few miles to the finish, we managed to catch up to, but not pass the boats in front of us. We crossed the finish line 5th and finished 6th with our handicap.


It was our first race as sailors and our boats first race, and frankly, we were ecstatic! We went to the Lottery Division special happy hour location and shared stories and tactics and it was clear that the current killed us. John, the skipper of Panache II, finished ahead of us and was throwing down some pretty good smack talk about how he would also teach us another lesson on Saturday. We both might have had a few rums in us when I poked him in the chest and said “see you on the line tomorrow, we’ll be the boat in front of you the whole way”.

Okay, I clearly have a ton for racing experience (one race, ha ha) but it was a matter of pride, and we have our secret weapons of Fogger and Dale on our team and these guys don’t take a loss lying down.

Saturday’s course was a long 12.5 miles upwind and into the big water, before heading back 12.5 miles to the finish line. We did a permanent repair on vang first thing in the morning and made sure our mainsail was perfectly tuned for the upwind leg. We synced with the warning horn and once again we were across the line first.

Knowing the issue with the currents, we quickly made our way toward shore and buzzed up the island. Only the Swan 48 managed to catch us, but after all, it’s a Swan, we’re on a Catalina (there is at least a million dollars difference in the purchase price). We pressed on upwind, with only the Swan in front of us and I took a lot of pride in looking back and seeing Panache II well behind us. When we got to the end of the island and turned directly into the big water and it was like we were hitting the brakes. We went from doing 6.5 – 7 knots down to 4.5-5 knots. The 25 knots of wind and 6-8 foot waves were crashing over the bow and drenching us and we slowly sloughed our way uphill around Pelican Rock. It seemed to take forever and Dale could sense my trepidation. He looked at me and said “don’t worry, we’ll get there…one boat length at a time”.

We did in fact round the island second behind the Swan and started making our way down hill. With the wind, the waves and the current in our favour, it was a real rush when we hit 9.4 knots. We were flying baby!

We maintained our position through the balance of the race and actually gained some ground on the Swan before crossing the line in second place. It was an amazing feeling! Fogger was grinning from ear to ear and felt we would get the bullet with our corrected time.

I checked online every 5 minutes waiting and waiting for the results to be posted. Finally we saw it! Silhouette finished in first place! We were thrilled!!

Race Results

That night at the Lottery Class happy hour I was really looking forward to talking to John from Panache II, but he didn’t show up. We celebrated (pretty hard) with the other racers before making our way to Kim Sha Beach where the big party was happening. I walked into the sailors VIP lounge and there was John. “Hey man, I didn’t see you at happy hour”, I said. He replied, “I didn’t think I could handle the gloating…enjoy your moment in the sun”. We shook hands and enjoyed a couple of drinks together before going our separate ways.



Day 3 racing was a bit of a blur. Our handicap changed dramatically and negatively as we had won the day before and our heads were a little cloudy from the prior evening’s celebration, but we had our third consecutive perfect start but crossed the finish line 5th overall.

That night was the awards ceremony on the big stage. When we were called up, the Heineken girls escorted each of us to the front of the stage where we were presented with our trophy. Lights, cameras, clapping… it was a total rush! We celebrated our success in fine fashion, and we enjoyed every minute of it!

We intend to enter the Heineken Regatta again next year . Fogger says “I think I created a monster”. I think he did too.

Fair winds and following seas,
Kelly Brown


Related Articles