How to Graduate from Cruiser to Racer — Steps to Start Racing Sailboats 🔉

By: Learn To Sail, North U

So often in the sailing world, we’re presented with a question that takes binary form — “are you a cruiser or a racer?” Sure, people tend to have their preferences, but I’d like to propose one can embrace both dimensions of sailing in the same way one can appreciate both fine art and Formula 1.

I have two boys who sail. One kid has a nice cheeseboard and understands the art of sailing, eating, and drinking on the ocean. His crew is consistently composed of competent sailors that want to relax and enjoy the ocean environment. 

The second son wants to go fast. If he is not going fast, he would instead take a nap  — the non-racing aspects of sailing aren’t interesting to him. His crew is a group of competitive sailors who love to win. They work well together as a team and can be found trying to go fast on a leisurely Saturday afternoon sail.

So many times I have wanted for both sons to experience the strengths of the other son out on the water — to become complete sailors, fully appreciative of the entire sailing experience, and also fully capable of maximizing speed and performance all in one optimized, well-rounded package.

In fact, this is not only my wish, but at American Sailing, it is our goal for every sailor out there to fall in love with both aspects of sailing. If you are already a seasoned cruiser, or just getting started sailing, here are a few steps on how to graduate to full-blown racer while still sharpening your general sailing skills.

What Are the Prerequisites to Sailboat Racing?

Learning to race sailboats involves a combination of theoretical knowledge and practical experience. First, you do need to have a grasp of the fundamentals of sailing. ASA 101 certification can get you in the front door of the racing environment. In addition, you should have knowledge and experience on how to maneuver the boat, trim the sails, and use the wind to your advantage.

With the Sailing Basics Behind Me, What’s Next?

Once you have gained knowledge beyond the simple skills you learned in ASA 101, these are a few ways to get started with sailboat racing.

Join a sail club or yacht club that offers and organizes local races. Being part of the sailing community will allow you to meet others interested in the sport. While the super serious racers might not invite you on their race boat, you can find a few skippers looking for crew. Wednesday night racing is a fun way to learn about sailboat racing and an excellent way to make new sailing friends.

Attend a clinic. North U is a new part of the American Sailing curriculum, and they specialize in helping sailors become more efficient out on the water. In the simplest terms, they teach you how to go faster, and this is accomplished through lessons on . seamanship, technique, skills, and even your ability to work as a team. This curriculum can be accessed through online courses, webinars, workbooks and best of all, the North U clinics that get you racing.

These clinics are a great way to familiarize yourself with racing and racing technique. You’ll learn about strategy, tactics, and rules. Take a look at some of the racing clinics that North U offers at

Learn the lingo of sailboat racing. While some of the common sailing terms are included, sailboat racing also has quite a few terms that you should be familiar with:

Here are some common sailing racing terms:

  • Beat – sailing upwind towards the windward mark
  • Reach – sailing perpendicular to the wind, at an angle between a beat and a run
  • Run – sailing downwind away from the windward mark
  • Tack – turning the bow of the boat through the wind in order to change direction
  • Jibe – turning the stern of the boat through the wind in order to change direction
  • Windward – the side of the boat closest to the wind
  • Leeward – the side of the boat farthest from the wind
  • Start line – the line across which boats start a race
  • Starting gun – the signal that starts the race
  • OCS – “on course side,” meaning a boat crossed the start line too early and must restart
  • Layline – the imaginary line that a boat must sail to in order to round a mark without tacking or jibing
  • Mark – An object the sailing instructions require a boat to leave on a specified side, and a race committee vessel surrounded by navigable water from which the starting or finishing line extends. An anchor line or an object attached accidentally to a mark is not part of it.
  • Mark rounding – sailing around a buoy or other fixed object on the course
  • Finish line – the line across which boats finish the race
  • Protest – An allegation made under rule 61.2 by a boat, a race committee, a technical committee or a protest committee that a boat has broken a rule.
  • Penalty – a penalty imposed on a boat for breaking a racing rule, typically a time penalty or a penalty turn.
  • Zone – The area around a mark within a distance of three hull lengths of the boat nearer to it. A boat is in the zone when any part of her hull is in the zone.

Familiarize yourself with the rules of sailboat racing. It takes time to fully learn the racing rules of sailing; they are complex and very detailed. Having a cursory glance at the basic concepts of the rules can increase your enjoyment, and whet your appetite to enjoy the more strategic side of sailing. That said, you don’t have to master all the rules to get out there and join a crew in a race to start enjoying the racing side of the sport. Many clubs have friendly competitions and entry level races to help you learn the art of racing.

Here are some of the most common or interesting racing rules:

  • Start: Boats must stay behind the start line until the starting signal is given. Crossing the line early can result in a penalty.
  • Right of way: When two boats are approaching each other, the boat on the starboard tack has the right of way and should be given room to pass. When boats are on opposite tacks, a port-tack boat shall keep clear of a starboard-tack boat.
  • Helping Those in Danger: A boat or competitor shall give all possible help to any person or vessel in danger.
  • Penalty: A boat that breaks a rule may be penalized by doing a 360-degree turn or retiring from the race.
  • Protest: If a boat believes that another boat has broken a rule, it can protest by flying a protest flag and informing the other boat at the first reasonable opportunity. The race committee will then investigate the protest and make a ruling.

Here are some resources to help you get started

  • Online Class: Sail Theory & Upwind Trim
    This online course provides a fundamental understanding of the forces behind upwind sailing as well plus advanced techniques that balance the angle of attack, sail depth, and the twist of your main and jib in order to optimize speed and pointing in all conditions.
  • Seminar: Racing Tactics
    This in-person seminar will teach the strategy and tactics you need to turn your speed into a podium finish. Starts, upwind, downwind, mark rounding: With top instructors and refined curriculum you’ll learn techniques to improve your game all the way around the course.
  • On The Water Clinic: Regatta Experience
    These events combine training and racing with coaching every step of the way. The clinics cover every facet of regatta success: Strategic planning, tactical positioning, starting, boat speed, trim, helming, boat handling – everything!

So, how do I bring my entire family up to speed so that we are winning Wednesday night races in our marina? Lately, we have been racing any other boat that is out on the water. Sure, those other boats have no clue that we are racing. However, when the three of us are sailing together, we are slowly attempting to go faster. This is a foreign concept to a couple of us as we don’t usually focus on trimming the sails but we have found the ride becoming smoother, and we are covering a lot more distance on our day sails.

The best advice I have been given about starting to learn how to race on a sailboat is quite simple. Practice. Practice makes a big difference. As of late, I am adjusting the outhaul, I am checking the boom vang, and I am keeping an eye on the traveler.  While my day sails have become busier, I am starting to see the value in wanting to occasionally be a racer.

Son 1, the kid with great taste in food. Well, he still watches in disbelief as he spreads his camembert on his crackers, but son two is now getting faster.

AD: Bulova