Hitchhikers Guide to the Caribbean Circuit

SinC Caribbean Circuit Sailing Guide

November 16, 2022

By Larry Huibers

If you’ve done it; you get it, if you haven’t; I’m betting you’ve spent a little (or a lot) of time dreaming of living the barefoot, lime in your beer lifestyle.

Azure waters of the Caribbean calls us like the sirens of the sea. For racers the winter racing circuit organized by the Caribbean Sailing Association is likely the very best four months of racing on earth. The challenge is how to get onboard. Flights from all over Canada are (relatively) easy, accommodations are plentiful, racing ranges mild to wild. The missing solution is a deck to plop your salt-soaked shorts on. 

Post Covid the Caribbean Sailing Association is getting back to its previous highs. More and more options present themselves, it’s a matter of knowing where to look. If you are a fancy pants Cat 3 sailor, you wait by the phone for your RBO (Rich Boat Owner) to tell you where and when to be there. That is not many people’s reality including most fancy pants Cat 3’s. 

Regular Joes make up the backbone of most sailing programs. You’re a regular Joe or Josee so let’s get you there:

Step 1; Be realistic about what you bring to a program. Your network of contacts contains your answer. If your rolodex is limited to local club or one design sailing that’s your skill, in the eyes of the critical crew boss. Don’t be discouraged – work every angle you know. 

SinC Caribbean Circuit Sailing Guide 2 400SinC Caribbean Circuit Sailing Guide 3 400

In the absence of scoring a big program ride you are actually in complete control of your outcome now. Options here include chartering a boat for an event. Buddy up with others and pick an event. The top Charter events are BVI Spring, celebrating its 50th anniversary this year. It will be an epic event and among the easiest to do logistically if you are in North America. Another fantastic event is the Heineken Regatta in St Maarten. Here too, the charter options are plentiful and staying on the boat next to the village is perfect. Both these events have really good You Tube exposure; go get lost in that rabbit hole for a while. The costs of doing these events are in line with any charter vacation, about $2,000 to $3,500 a week/ person based on 6-8 people. 

Stepping it up in the charter option includes St Thomas International Regatta. Now you get three others and charter an IC24 to one design race. Enjoy tight one design racing guaranteed to put a smile on your face. IC24s are modified J24s with a Melges 24 style cockpit. You charter for the week and stay in villa on Cowpet Bay. The St Thomas YC in USVI has details. 

More options to fill your racing needs open up when you enter the world of racing charters such as Sea to Sky, Ondeck, Global Racing, LV Yachting and Ocean Racers, companies that provide positions for individuals seats or groups on hot boats. The choice of boat and number of crew becomes very customizable and is an excellent way to experience top level racing on yachts starting at 40’ and up. Costs are reasonable and they take of all the difficult parts; the yacht will be well prepped and ready for your arrival.  My experience with these programs supports that it’s an excellent way to get racing. 

Scarlett Oyster is one of the more successful programs with wins in most of the major events including the Caribbean 600. Information on these programs is available through the regatta websites and Yachtscoring page. Additionally, there is local boat options, like the Savvy program in Grenada. Those guys had more than most anyone else and was a great balance of fun and serious racing, each event has its own local thing, research what it is, it could be just right for you. 

SinC Caribbean Circuit Sailing Guide 4 400Be prepared to commit time. This requires the most amount of effort on your part to locate a private yacht doing the event and find a way to get on their crew. Review previous regatta results to see if you have any connection with a boat and begin by offering your services. Focus on what value add you bring, cooking, specialized boat skills etc. This makes you more attractive in a competitive world. Reality is not everyone is able or willing to burn a week or two of vacation time to ride along, if you can offer that you are in limited company. Work that angle hard, you know how often a boat is just one or two people from being staffed to get around the bases. 

The CSA rating system has online viewable current and outdated certificates. Included in the certificate is the max crew weight. It’s a well-known fact that boats sail best to their rating if they are at or close to max crew weight. The trade winds blow and weight on the rail may be your very best asset. The CSA rating system is very finely tuned for the prevailing breezes and is super competitive, there is good reason that maximum weight is sought after.   

Finally, if you are risk taker you can always just go down and walk the dock a few days ahead. Start with the organizers, try to local sail loft, or hang out at the yacht club. You’ll meet the nicest people and maybe score the greatest ride of your life.   

For me, I was very lucky to race on four Corinthian boats in the south. My experience had a lot of horseshoes of good luck tied to it and I am incredibly grateful for the experience. For five winter events we averaged on a 40’ boat that it required a total of about 30-35 people to do effectively with ten on the boat each race – three core and seven rotating crew. That a lot of people if you consider how hard it is to get crew for a few weekend home regattas or regular Wednesday nights. Don’t underestimate what value you bring to a program, be realistic (unless T Hutch already has your number, he isn’t cold calling you) and then commit to doing it. It’s all doable and costs are more than fair given you don’t own a boat in the Caribbean. 

The Caribbean Sailing Association runs top shelf events, I won’t rate the events, they are all quite spectacular and distinct. I enjoyed every one of them and you can’t go wrong with any. The CSA calendar is designed to complement each other and is well established years going forward.  

So, if not you, who? If not now, when? The sun, sand and wind are calling, do the right thing and answer the call. 


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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