Skip to main content

Preparing for a Doublehanded Race

By equipping your boat for doublehanded racing you will also make it a better boat for cruising 

By equipping your boat for doublehanded racing you will also make it a better boat for cruising 

A few months ago we took a look at the development and attraction of doublehanded racing (Two to Tango, June/July 2020). Hopefully, that served to whet your appetite. If so, the question becomes: “How do I get started?

The good news, as we explained in Part 1, is that if you are the owner of pretty much any kind of sailboat from around 25 to 55 to even 60ft in length, there are more than likely already a number of regattas in your area that would love to have you join them. Again, you don’t need to sail a high-octane Class40 racer to have fun or even bring home a brag flag or two.

More good news: prepping for doublehanded racing is anything but a single-use project. Pretty much anything you do to your Sabre, C&C, Tartan, Jeanneau, Beneteau, Hallberg Rassey, Dufour or Catalina for doublehanded “racing” will serve to enhance your cruising experience as well. Let’s look at some of the areas that warrant consideration.

An example of a polar diagram (for the Dehler 30 One Design shown below): The curved lines indicate the boat’s optimum speeds at various wind speeds and wind angles; the different colors correspond to different headsails 

An example of a polar diagram (for the Dehler 30 One Design shown below): The curved lines indicate the boat’s optimum speeds at various wind speeds and wind angles; the different colors correspond to different headsails 


Assuming your boat has a mainsail with a couple of reefs and a general-purpose 130 to 140 percent roller-reefing headsail, you are well on the way. Discuss with your sailmaker the difference between roller-furling (in which the sail is either fully rolled up or fully deployed) and roller-reefing (where the sail can be partially furled or deployed, as is the case aboard most cruising boats). It is also quite likely you will have a cruising spinnaker of some kind.

Most likely this is in a sock, or perhaps, on a top-down furler. Congratulations, you already have all the sails necessary for competing in most short races, like the Larchmont Yacht Club’s Edlu Race on western Long Island Sound (, which had 14 doublehanded boats in 2020, and offers a 35-mile course for boats with spinnakers or 20 miles for those without and the fascinating Three Bridge Fiasco (which typically has a doublehanded division, though not in 2021), run by the Single Handed Sailing Society in San Francisco ( Other options for those with more extensive offshore experience might be the Ida Lewis Yacht Club’s annual Distance Race ( out of Rhode Island’s Narragansett Bay or the Queen’ Cup organized by Milwaukee’s South Shore Yacht Club ( on Lake Michigan—both overnighters.

For longer races of 100 miles or more, you will also be required to have some smaller sails on board for severe weather. Some boats come set up with an inside staysail stay. If your boat does not, then a Solent stay is a good option for flying a storm jib, although this additional stay will require a bit of forethought in design and layout. The sail will also require a pair of sheets.

Today, almost every cruising boat has everything needed for navigation already on deck. Personally, I prefer having a multifunction display screen in the companionway area mounted on a swing-out gooseneck as opposed to on the binnacle. That way it can be seen either on deck or from below. Of course, navigation data can also be arranged on a tablet these days.

Thanks to years of development by offshore solo racers, today’s autopilots are more reliable and the software driving them better than ever. The key is to have a system that allows the autopilot’s computer to steer to the true wind direction and angle, and true windspeed. Spending the money to have an underdeck-style autopilot, as opposed to the simpler, less expensive on-deck variety has a few advantages. Among them: it is (or should be) drier down below; you can get a much more powerful ram bolted to the quadrant, and in the event, you suffer a steering cable failure, you have emergency steering at the press of a button. Combined with the aforementioned true wind functions, this arrangement will allow you to get the best value from the rest of your boat’s setup

Get in as much practice as you can: that includes working on MOB and other safety drills 

Get in as much practice as you can: that includes working on MOB and other safety drills 

Safety Gear

Really, all of the kit needed for doublehanded racing is worthwhile having on your boat anyway, especially if you plan to range over a fair bit of distance in your cruising. Your starting point here will be the Safety Equipment Requirement (SER) put together by US Sailing ( A consolidation of the World Sailing “Offshore Regs” outlining every conceivable detail of boat and race type, the SER’s can be downloaded for free off the US Sailing website. This and World Sailing’s Offshore Special Regulations, updated every two years also down-loadable from World Sailing site ( are fantastic resources for safety relates issues of any kind and are a worthy read.

If you have ever done any kind of safety-at-sea seminar, you will be familiar with much of what these two documents discuss. Topics include everything from gear stowage charts to details regarding different types of flares, emergency steering, MOB gear, EPIRBs, life jackets, harnesses, spare nav lights, fire extinguishers, watertight handheld VHF’s, everything.

Having some kind of liferaft, even a modest, inshore, no-canopy number is, I suggest, better than nothing when sailing places like Block Island Sound or the lower Chesapeake. Of course, if you want to go farther offshore, a suitable offshore liferaft is both a requirement and something you definitely want to have aboard if the worst ever happens.

Jacklines, in addition to being necessary for going forward safely, should be securely installed and taught so you don’t ever find yourself dragging through the water if you go over the side. After dark, especially, you should always call up the other crew from their bunk if ever you have to leave the cockpit, in case something should happen. And of course, make sure your lifelines are sound!

A few items I make sure are always in my own kit whenever I go offshore include a crotch-strap harness and inflatable PFD, a waterproof flashlight that I keep with me at all times, a handheld VHF and a SHARP knife.

Food and Water

Pre-prepared food is best. Personally, I prefer protein to carbohydrates. The latter makes me sleepy. Whatever your dining preferences, prepare as much as you can before leaving the dock. You’re going to have plenty to do and want to be sure and rest up as much as you can when you’re not on deck once you’re underway. Home-cooked soups and similar can be frozen and then reheated as needed.

Before “hydration” became a thing, we used to drink a can of soda every few hours—maybe. Today, we know better. Fill those reusable water bottles and have them close at hand, not just at the bottom of some rope tail bag! Get some bicycle water bottle holders and mount them around the cockpit, so you can take a sip whenever you want, quickly and easily. Do your research on dehydration and mental acuity degradation. It is not good. Bottom line: stay hydrated. Prepare for night watches by brewing up your favorite 0230 hot drink in advance and then stowing it in a multi-cup thermos. There are only two of you so should be simple.

Performance and Boatspeed

Performance has many elements to it, but when starting out there are three bits of information you will want to focus on: true wind speed, true wind direction and boatspeed.

To ensure you are sailing your boat up to its potential, obtain or construct a polar diagram for your boat. “Polars” display how fast a boat should be going at a particular true wind speed and point of sail. Not sailing “to the polars,” as we say, means you should be going faster. You can get polars for many production boats from US Sailing or the boat’s class association or even a Facebook group. If not, make your own. Note the boatspeed, wind speed and true wind angle at two-minute intervals as often as you can when sailing. You can get a data logger and hook it up to your instrument’s CPU (although you better like messing with wiring and software to do this).

Either way, having a set of target speeds to aim for can help keep you focused, especially in the middle of a graveyard watch when all you want to do is crawl back into your bunk. Something to keep in mind: offshore races are often “won at night” by the crews that keep pace as opposed those that slack off when they start to feel sleepy.

Picking the right shipmate for doublehanded racing is crucial  

Picking the right shipmate for doublehanded racing is crucial  

Crew Management

In addition to making sure your boat is ready for the rigors of voyaging offshore, it’s also important that the crew be prepared for the physical aspect of doublehanded racing. Pace yourself physically, think twice before committing to an action and don’t wear yourself out too soon. Cold, wet and weary crew is a liability. Good foulweather gear and lots of fleecy layers are critical, even if you think the weather is going to be mild. After dark, it still gets chilly. Shun cotton. In addition to being incredibly rewarding, doublehanded sailing can also be demanding. Know your physical limits. Fatigue is dangerous. Being aware of when you and your shipmate are most and least alert is also important. The ability to make the correct decisions at the right moment is critical.

As a practical matter both members of the crew ought to be able to operate the boat and make the necessary navigation and sail trim decisions without waking the other. One of the fun things about doublehanded racing is that it’s like crewed racing, only without the clutter. The entire crew can be fully involved in all decisions. Rather than just sitting on the rail, you will both be in the thick of everything, all the time.

Before hitting the starting line, thoroughly practice both boathandling and safety drills. “Tiller time is king” holds true of this kind of racing, too. When practicing with your safety gear, man-overboard drills are, of course, paramount. There are, however, a good seven or eight other emergency procedures you need to prepare for as well. These include failed steering situations, a broken rudder, fire, a holed hull, a broken mast and medical emergencies. These all need to be discussed in terms actions and the necessary kit you need to have to aboard. Try sailing your boat with the emergency tiller rigged. It’s not easy.

As part of your race prep get in as much multi-hour sailing as you can, as opposed to just going out for short stints. The good news is that coordinating two people’s schedules is much easier than coordinating a crew of 10—one of the reasons for doublehanded racing’s appeal! If you need to move the boat to the race venue, do so with your co-skipper and use that time for practice.

Finally, as with any other kind of sailing, having the “right person” as co-skipper is critical. Sailing ability is important, of course, as are things like a knowledge of mechanics, computers and boat repair. But at the end of the day, trust is the most important thing of all. Weather smarts and sail trim can be learned. Being a good shipmate, not so much. Proactive decision making and knowing when and how to take the right kind of action are central to doublehanded racing—again the same as with any other kind of sailing. The difference is that when racing doublehanded, it’s just the two of you.

I’ll tell you right now, it’s not always easy. There may well be times when, as with other sailing, you think never again. At the same time, though, when you can finish and the crewed boats don’t, that’s a feeling, a sense of satisfaction that is unobtainable anywhere else. If you have any interest at all in this kind of challenge, you owe it to yourself to give it a try. 

Where to race

Below are a number of regattas offering doublehanded sailing  as well as some organizations to help point you in the right direction.

Bayview Mackinac Race

Bermuda One-Two Yacht Race

Chesapeake Shorthanded Sailing Society

Chicago YC Race to Mackinac

Great Lakes Single Handed Society

Ida Lewis Distance Race

Lake Michigan Singlehanded Society

Marblehead to Halifax Race

Newport Bermuda Race

Newport Yacht Club

Pacific Cup

Pacific Singlehanded Sailing Society

Singlehanded Sailing Society

Joe Cooper is a sailing coach, instructor and consultant specializing in shorthanded offshore sailing. He is also a consultant for Quantum Sails. Learn more at

April 2021


Alexforbes Archangel1-1 (14)

Cape2Rio Draws to a Close

With just four boats still on their way, it has been a long road to Rio for the fleet competing in this year’s Cape2Rio. Larry Folsom’s American-flagged Balance 526 Nohri took line honors and a win in the MORCA fleet, finishing with a corrected time of 18 days, 20 hours, and 42 more


Close Encounters: A Star to Steer By

I first met Steve and Irene Macek in the proper way—in an anchorage full of bluewater cruising boats. This was in St. Georges, Bermuda, in the spring of 2019. Theirs, without doubt, was the most distinctive boat there—an immaculate, three-masted, double-ended Marco Polo schooner more


The Ocean Race Leg 2 Kicks Off

After a trial by fire start to the race and only a brief stop for limited fixes, the five IMOCA 60 crews in The Ocean Race set off for Cape Town, South Africa, early on January 25. Despite arriving somewhat battered in Cabo Verde, an African island nation west of Senegal, the more


Cruising: Smitten with a Wooden Boat

I was sailing down the inner channel of Marina del Rey under a beautiful red sunset when Nills, one of the crew members on my boat, pointed out an unusual and unique-looking 40-foot gaff-rigged wooden cutter tied to the end of a dock. Its classic appearance was a stark contrast more


Racing Recap: Leg One of The Ocean Race

New to spectating The Ocean Race? Managing Editor Lydia Mullan breaks down everything you need to know to get started. more


From the Editor: Keeping the Hands in Hands-On

SAIL Editor-in-Chief Wendy Mitman Clarke enjoys a sunny autumn cruise in her Peterson 34 on the Chesapeake Bay. It was late afternoon just after the U.S. Sailboat Show in Annapolis when I climbed aboard the last boat on the schedule. I and others who review and sail boats for more


B&G Announces New Zeus S Chartplotter

B&G has long been putting out top-of-the-line electronics, but the new Zeus S Chartplotter is a new take on the best way to give sailors the exact information they need, when they need it. “So many more people sail shorthanded these days, whether as a couple or when they’re more


Charter: Mission to Mars

In the wake of the pandemic, many sailors are seeking adventure and grabbing onto a vision of their best lives. For some, that may mean sailing across the Atlantic with the ARC (Atlantic Rally for Cruisers) while for others, it could be a yacht charter in the Caribbean. The more