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A Racer’s Bucket List

Peter Nielsen suggests seven fun regattas to race in before you hang up your sailing shoes
You’re guaranteed a solid few days of excellent sailing at Cowes Week

You’re guaranteed a solid few days of excellent sailing at Cowes Week

The Heineken Regatta

Need a dose of warm sunshine, hot competition and strong breeze to shake off the winter blues? The annual Heineken Regatta is perfectly timed and placed to provide all three. It’s four intense days of racing around the island of St. Maarten/St. Martin, featuring everything from grand prix boats to charter boats. As an added bonus, the onshore party scene is legendary. How do I take part? There are pay-to-play spots available on race boats that contest all the Caribbean events. Alternatively, enter the bareboat class and have just as much fun. Dates: March 5-8. More info: heinekenregatta.com

Sperry Charleston Race Week

Since Key West Race Week’s demise, this East Coast regatta has cemented its place as the go-to event for early-season competition. Top one-design racers from all over the country flock here for tight competition on these tactically challenging waters with their strong currents and often gusty breezes. Apres-sail, you can take advantage of Charleston’s many fine restaurants. How do I take part? If you’ve got good racing chops, stick your bio on the crew board on the race website. This year, you can also get a crew together and charter an RS-21 keelboat. Dates: April 23-26. More info: charlestonraceweek.com

Cowes Week

England’s premier regatta, this weeklong event originated in 1826. It is held on the testing waters of the Solent, with classes for all kinds of boats. Typically, more than 1,000 boats take part, and there are 40 race starts each day. It’s estimated that around 8,000 sailors compete in this annual regatta, from Olympic-level professionals to enthusiastic amateurs. Conditions vary widely during the week of racing, making a victory here well worth bragging about. How do I take part? The easiest way is to either book a crew spot on one of the fleet of Sunsail charter boats, or charter a boat for you and your crew. Dates: August 8-15. More info: cowesweek.co.uk

Antigua Classic Yacht Regatta

Who could fail to be stirred by the sight of a fleet of beautiful classic yachts duking it out on the sparkling blue waters of the Caribbean? What the Antigua Classics lacks in sheer numbers of entries is more than compensated for by the sheer size and quality of the boats that do take part—everything from tall ships to Dragons. How do I take part? Some of the entrants take paying crew—check with the regatta organizers. Alternatively, there is a small fleet of Dragons available for charter. Dates: April 1-7. More info: antiguaclassics.com

Kiel Week

Originating with a race among 20 boats in 1882, Germany’s Kieler Woche (Kiel Week) now lays claim to being the world’s biggest regatta. It attracts more than 2,000 boats, from Lasers through all the Olympic classes to Clubswan 50s, and the entire city joins in for a week of cultural and culinary festivities that brings in more than 3 million visitors. How do I take part? If you’re a one-design sailor, check out your class’s website or Facebook page for crew opportunities, or see if you can beg, borrow or charter a boat locally. If you just want to spectate, there are plenty of opportunities. Dates: June 20-28.
More info: kieler-woche.de

Cork Week

At 22 years old, this regatta is a mere stripling compared to some of its rivals, but it can’t be beaten for sheer atmosphere, friendliness and good-old Irish craic. There’s a mix of one-design and IRC racing, with both spinnaker and non-spinnaker classes, and entries vary from ancient racer-cruisers one-designs and sharp new raceboats. If you want to dip a toe into European racing, this low-key but fiercely contested regatta would be a good start. How do I take part? There is a crew board on the website, along with a list of boats available for charter. Dates: July 13-18. More info: corkweek.ie

The Rolex Big Boat Series has San Francisco for a backdrop

The Rolex Big Boat Series has San Francisco for a backdrop

Rolex Big Boat Series

Run by the St. Francis Yacht Club, the West Coast’s biggest inshore regatta features hard racing on the often foggy, always testing waters of San Francisco Bay. A variety of one-designs and big boats racing under ORR make up a large fleet that often incorporates world or national championships. How can I take part? There is a crew board on the website, and there are often boats available for charter. Dates: September 17-20. More info: rolexbigboatseries.com 

January 2020

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