Which Caribbean Regatta is for You? The Choices are Hard – Part 1

SinC Caribbean Regattas

November 30, 2022

By Larry Huibers

Last year in Grenada

Like the Bits and Bites commercial, every handful is different. Racing the Caribbean Sailing Association winter series is like that. Based on positive feedback from the Hitchhikers Guide, I thought I’d highlight the events based on my experience.

Starting by date of event here is my take:

Grenada Race Week; January 29th through Feb 3.

This is an undervalued event and high on my list. I really like the island, its old school Caribbean, not over-developed and dated in a very positive way. Because it is below the traditional hurricane paths its infrastructure is solid and not getting replaced because of big storms. This adds a charm that is tangible when strolling around. I find the people exceptionally friendly and helpful, genuinely happy to share their island with you. 

Because this regatta is early in the season and below the normal island traffic, it isn’t heavily attended, which is a shame. The event dates match up to the big beach festival along with the island boat races; super fun to watch from Grand Anse, one of the nicest beaches in the world for sure. Racing takes place on both protected waters and out in the big ocean, creating challenges befitting a major event. Lately, they have added a race out to Carricou which I understand is stunning. That may challenge the accommodations of crew but worth the trouble.

SinC Caribbean Regattas 2 400Like each event there will be a couple of talented local boats that don’t do the whole circuit but are extremely well sailed and tend to know local tides and currents making them formidable competition. The island has unique landscape with black sand beaches, rain forest in the mountains and outstanding diving; great to explore on free days. In St George’s BB’s Crab Shack has many memories etched into the ceiling, bring a sharpie and leave your own memory; see if you can find Touch2Play (the Canadian boat Rob Butler competed with for years) – we’re up there somewhere. 

Getting to the island is quite easy with direct flights from Toronto and other major cities. On island, St Georges University has many North American’s studying medicine and veterinarian so they are well tailored to North Americans. There is a charter base out of Port Louis in St George’s adding to the simplicity. As will be my normal advice for each and every Caribbean event, get down to this one, you’ll love it.

RORC Caribbean 600; February 20-24


The granddaddy of them all. This is one of the major ocean races around the world, right up there with the Newport to Bermuda, Fastnet, Middle Sea race and others. This race attracts the big yachts and weaves its way through the islands. 

Starting and finishing in Antigua it goes as far north as St Maarten and south to Guadeloupe. Never going straight for more than a hundred miles at a time it is a tactically and boat handling challenge. Racing under IRC and CSA rating systems makes it fair to all boats, big and small. 600 miles can be done as quickly as under two days or as many as four. 

Just because you are rarely out of sight of land doesn’t make it any easier as the wind ranges from a little to a lot. Look at past event results and video presentation, you’ll get a sense. Participation averages about 100 boats including large multihulls. Unlike point to point in cold water races, this one is more comfortable; warm water and warm breezes makes foul weather gear less critical, no toques required. If you are into distance racing this one is definitely on your bucket list. 

St Marten Heineken Regatta March 2-5th

Using their tag line of “Serious Fun” this one is Woodstock meets Sailing. The party scene is off the chart, the locals share the fun with the sailors leading to a crazy party vibe. The quality of the musicians is fantastic, including headliners like the Jackson Family, UB40 and Shaggy. True to its island roots, and consistent with all regattas, reggae is the base sound. (If you want both kinds of music; country and western this ain’t the place.) Simpson Bay creates the perfect location. The bridge opening, allowing boats back into the bay, makes for its own event with crews scoring points from the watchful eyes of those at the yacht club viewing station. Special awards are handed out at the big prize giving adding motivation to the crews. 

Not to be outdone by shoreside shenanigans, the racing is spectacular. The regatta organizers run two courses allowing the large charter fleet to race among themselves and the race boats to run courses that match their strengths making it fun for all. The splitting of charter boats from race boats happens at all the events that have charter divisions. This acknowledges why the charter crowd participates and rewards them with courses that meet their wants. All regatta organizers take a keen interest in making their events better and are very open to input from participants. The blend of Windward/Leeward and distance races all happening in day light hours mixing it up just right. The around the island is always a highlight and the scenery is spectacular. You must remind yourself to look around, sights you won’t see in many places and likely one of the reasons you are here. 

SinC Caribbean Regattas 4 400SinC Caribbean Regattas 5 400

Accommodations are readily available and it’s a great place to front or back end the regatta with serious vacation fun and local food. BBQ ribs on the French side and bitterbollen on the Dutch side are a must, along with ice cold Heinekens. 

For this event read the race instructions; starts and finishes make sense once you read the instructions. The regatta village at the Princess Port de Plaisance gives you great access to the regatta site as well as quality docking for the boats making it all easy and no car needed. This is one of the big events and clearly people are voting with their feet showing that it’s a great event.  

Next instalment: St Thomas, BVI and the legendary Antigua Sailing week


SinC Larry Huibers 400Larry Huibers

Sailing on the south shore of Lake Ontario, Larry and his wife and daughter have been sailing both one-design starting in their J22 and then transitioning to PHRF with various boats, most recently in Laser28 and Esse 850.
Lucky enough to race with some wonderful boats and greater crews on the Great Lakes, East Coast Southern US and the Caribbean. Currently trying to give back to sailing through volunteering with PHRF LO as current president.



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