The racing never stops in the many islands of the Eastern Caribbean, but the major events — most of which are from Antigua north for English speakers — run from late January to early May. In addition to the really big races and regattas listed below, there are countless great smaller ones such as at Bequia, Trinidad, Grenada, and just about every significant island. Here’s an overview written for the average enthusiastic sailor:
- Jan. 25-27 — Superyacht Challenge Antigua. Having seen the success of the St. Barth Bucket, Antigua wanted in on the fun and money. Eighteen excellent boats between 100 and over 200 feet competed in this year’s event.
- Feb. 18 — Now in its fifth year, the RORC Caribbean 600 — which starts in Antigua and weaves its way through a number of islands before ending in Antigua — has quickly become one of the more prestigious middle-distance races in the world. Approximately 50 boats, ranging in size from 36 feet to the 215-ft all-carbon ketch Hetarios are expected.
- Feb. 28-March 3 — The four-day St. Maarten Heineken Regatta, now in its 33rd year, has attracted as many as 298 entries a year, in everything from the world’s greatest big racing yachts, to a one-design class of big Gunboat catamarans, to nearly 100 charter boats. Yes, it’s a monster regatta, which has featured monster musical acts such as the Black Eyed Peas, Maxi Priest and Wycliff Jean. The whole island seems to embrace the event, which revels in the reputation for partying like Americans haven’t done since 1969. Given the size of the regatta, if you show up, you should be able to get a ride. Tiburon’s Rick Wesslund and his Bay Area crew on the J/120 El Ocaso took the Most Impressive Boat in the Regatta award last year, and are going back. Patrick Adams of Mill Valley, captain of the Swan 105 Varsovie, will also return, as will the O’Conner/O’Conner/Stompe team, scourge of the charter boat fleet. With a little luck, we’ll be doing the Heine with the Olson 30 La Gamelle, main and #4 only, in the Lottery Class, which is a catch-all division where ratings are changed every day to keep the racing close.
- March 20-23 — The Loro Piana Caribbean Superyacht Regatta and Rendezvous at the Costa Smeralda YC in Gorda Sound, British Virgins Islands. Having seen the success of the St. Barth Bucket, the Italian clothing company and the new yacht club wanted in on the superyacht action, so they started this event. It attracted 14 top-quality superyachts in its first year, and they expect even more this time around. If you want to rub shoulders with the very rich, or maybe land a spouse who owns a jet, the Costa Smeralda YC wouldn’t be a bad hunting ground. The yacht club is located a winch handle’s throw from the Bitter End YC and all the charterboat moorings in Virgin Gorda’s North Sound.
- March 25-31 — The BVI Spring Regatta and Sailing Festival says they’ve got "something for everyone, no matter if you are a racer, cruiser, or just come to party." It’s true, because if you’re hardcore, you can sail the entire six-day event. If you’re softcore, you can do either three days of racing or three days of the festival. While they do get some fine boats, it’s more locals and weekend warriors than some of the other events, and more casual in a good way. Stephen Schmidt of the South Bay, who sailed away to the Caribbean ages ago with his custom cruising Santa Cruz 70 Hotel California Too, will be back for the umpteenth time, and is usually looking for crew. If you even look like a sailor, you shouldn’t have any trouble getting a ride. It’s a shame the Spring Regatta has conflicting dates with the St. Barths Bucket.
- March 28-31 — St. Barths Bucket. Yachting World has called this "the greatest sailing spectacle in the world" and there is no way we could disagree with the evaluation. Imagine 40 invited yachts from 100 to 289 feet going at it in three races in the spectacular open waters of the Caribbean. At night, almost all the boats line up on one quay in a harbor the size of Belvedere Cove to party, party, party, French Caribbean-style. The fleet is big enough that if you know your stuff, you probably already know somebody on a boat, and therefore have a decent shot at getting a ride. But to our thinking, this is one regatta where we prefer to be a voyeur rather than a participant. Four J Class boats, the 289-ft Maltese Falcon, the Los Angeles-based 100-ft Symmetry, and the 200-foot-ish schooners Adela and Athos will all be back.
- April 8-13 — Les Voiles de St. Barth. This is sort of a St. Barth Bucket for people with boats shorter than 120 feet. The relatively new event attracted about 60 boats last year, and with 36 entries already, expects a bigger fleet this year. It offers the same great sailing as in the Bucket, but with even more casual French Caribbean-style partying. If you can sail, there’s a decent chance you can get on a boat, such as Schmidt’s Hotel California Too. Kenny Keefe of KKMI will be back organzing things on Jim Swartz’s TP 52 Vesper, and the mightly Irens 63 trimaran Paradox, which has Bay Area connections, will also return.
- April 18-23 — Antigua Classic Yacht Regatta. If you love classic yachts, there is nothing that compares to the Antigua Classic Regatta. It’s great boats, great racing, and great fun at a terrific historical site. Top honors last year went to the Robert Clark 65 Lone Fox, owned and sailed by Ira Epstein of Bolinas, a long time veteran of the event. There are often good opportunities to crew in the Classic. Even Dennis Conner walked the docks and got a ride last year.
- April 28-May 3 — Antigua Sailing Week, now in it’s 46th year, is the grandaddy of all great sailing weeks in the tropics. We did six of them with our Ocean 71 ketch Big O in our younger years, and it’s a miracle we survived coming off Cades Reef on port so many times in the face of a mob of starboard-tack boats — to say nothing of the drinking and general week-long debauchery. After years of 200+ entries from around the world, Sailing Week took a big hit with the Great Recession a few years back, but is now back to the five races plus the Yachting World Around the Island Race. As of mid-January, they had 98 entries — including Rick Wesslund and El Ocaso — so maybe the old girl is back up to speed. But, like us, she’s gotten more mellow with age.
This certainly isn’t a definitive list of great regattas in the Caribbean. There’s the great Bequia Heineken Easter Regatta in the charming little island of Bequia, big regattas in Trinidad and Grenada, to say nothing of the massive sailing crazy French regattas on Martinique and Guadeloupe.