There's a First Time For...Racing Your Cruiser

For years, you’ve watched raceboats strut around the buoys, their crews tweaking lines or pulling off well-choreographed maneuvers requiring hours of practice and polish. While cruising may be your raison d’être, you can’t help but notice that racers know how to really make a boat go, a useful skill for any sailor.
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For years, you’ve watched raceboats strut around the buoys, their crews tweaking lines or pulling off well-choreographed maneuvers requiring hours of practice and polish. While cruising may be your raison d’être, you can’t help but notice that racers know how to really make a boat go, a useful skill for any sailor.

For years, you’ve watched raceboats strut around the buoys, their crews tweaking lines or pulling off well-choreographed maneuvers requiring hours of practice and polish. While cruising may be your raison d’être, you can’t help but notice that racers know how to really make a boat go, a useful skill for any sailor. There’s also no denying the appeal of having another excuse to spend the evening, day or weekend out sailing with your friends and family—not to mention having another great way to enjoy your boat. 

Fortunately, while top-flight racing can be mind-numblingly complex, the grand prix scene represents only a tiny percentage of the game. And while experience helps, you don’t need years of practice to enjoy a great day of racing. Here are 10 tips for racing your cruiser, with an eye toward minimizing the learning curve and maximizing the fun.


Regattas come in all flavors, sizes and styles, allowing racers to choose events based on their skills, confidence and experience. Generally speaking, basic regattas are the place to start. Here’s an overview of types of first races to consider: 

Beer-Can Racing: Most yacht clubs offer some kind of informal, fun-minded midweek racing program. This is a great way to learn the ropes in a low-key environment. Typically, the socializing afterward is as integral to the event as the racing itself, and beginners are almost always welcome. 

Pursuit Races: A fantastic option for beginners and experts alike is the “pursuit” format, in which the race committee starts boats according to their performance characteristics, with the slower boats starting first and the faster boats starting later—first boat to the finish wins. This works especially well on longer courses, since everyone finishes around the same time, ensuring good attendance at the after-race party. It also allows newbies to try racing without having to negotiate the controlled chaos of a typical starting sequence. New England-area sailors can check out the annual Figawi race from Hyannis to Nantucket Island (

Distance Races: For many experienced cruisers, distance racing is a great entry into competitive sailing, as it draws more heavily on offshore cruising skills than twitchy buoy-racing moves. While the distances are often similar to long cruises, the pace and tactics are what’s decisive. Examples of a manageable first distance race include the Storm Trysail Club’s 186-mile Block Island Race (, the Royal Victoria Yacht Club’s 139-mile Swiftsure Race (, the Lakewood Yacht Club’s 150-mile Harvest Moon Regatta ( or the 76-mile Queen’s Cup ( 

White-Sail Divisions: Almost all Caribbean regattas, plus plenty of North American races, offer a jib-and-main, or “white-sails” class, in which competitors only fly mainsails and jibs. If your crew’s spinnaker handling is shaky, white-sail races are the place to be.

Cruising Classes: Many bigger regattas are waking up to the fact that plenty of sailors want to participate and compete in a less-serious environment. Cruising classes sometimes fly spinnakers, sometimes not, but they all emphasize friendly competition, rather than cutthroat tactics. Super-competitive Sperry Top-sider Charleston Race Week, for example, just introduced a new pursuit-style cruising class section this past spring ( 


Virtually all keelboat racing uses a handicap system (think golf) to allow different types of boats to race competitively. Most friendly racing in the United States uses the Performance Handicap Racing Fleet system (PHRF)—contact US Sailing ( to obtain your PHRF certificate. The process varies depending on the make and model of your boat. Common designs from builders like Catalina or Beneteau often have established PHRF handicaps, while one-offs and less common boats will require measurement.


Mark roundings and tacking duels may appear complex, but they only require a basic knowledge of the rules. Step one is to acquire a copy of ISAF’s The Racing Rules of Sailing

(, as well as a book or two on racing tactics and strategy. Dave Perry’s Understanding the Racing Rules of Sailing is a great resource that includes both a complete set of rules and some easy-to-understand explanations. For a good general introduction to racing, try Getting Started in Sailboat Racing, by SAIL senior editor Adam Cort. Step two involves taking a course with a racing-focused program such as J/World ( or North Sails’ North U ( To really jump-start your racing program, consider hiring a private sailing coach. 


Foster a positive learning-friendly environment where clear, respectful requests and commands are the only acceptable form of communication. Expect things to happen more slowly than you’d like. Expect bits to break and sails to rip. Mistakes are part of the game, and the skipper who stays calm, collected and analytical is usually successful and well liked. He or she will also have a much easier time finding and retaining crew. 


Until you’re feeling solid on your Racing Rules of Sailing, as well as the local etiquette, consider employing the time-tested strategy of holding slightly back to avoid the worst of the starting melee. The same goes for mark roundings. Don’t just stick your bow into a crowd and hope for the best. You’ll have plenty of opportunities to catch up during the rest of the race without subjecting boat, crew or skipper to unnecessary trauma. 


This is our sport’s national governing body and an organization that strives to ensure fair competitive racing nationwide. Members also benefit from useful courses and symposiums, website resources, and the Safety at Sea Seminar, which is a requirement for many distance races.


Often a good “ringer,” or ace, can help crewmembers to better understand their individual roles and can significantly accelerate a team’s overall learning experience. Sailmakers will also occasionally take clients (hint: or prospective clients) out for “sail evaluations,” which could be “scheduled” during a local race.


While actually racing is usually the best way to improve your results, novice crews would do well to spend some time practicing sail trim and boathandling. The objective should be to run through as many racecourse scenarios as possible, without the intimidating presence of a hungry fleet. Practice in all wind ranges, particularly heavier conditions. Make sure your crew is acclimatized to setting and dousing spinnakers; practice mark roundings using convenient buoys; and get everyone comfortable quickly shifting from upwind work to reaching and running. 


It seems obvious, but a clean underside makes a huge difference. Aside from dangling bumpers, few mistakes telegraph “newbie” faster than a furry undercarriage.


Only one boat can win, but everyone can have fun. Create an environment where grins—not finishing order—dictate success. Embracing competition is great, but remember that your original reason for racing was to spend time with family and friends in a wonderful environment—not to collect “pickle dishes,” or trophies. Get this part right, and everything else will eventually click as well.

Photo by Rebecca Waters


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