Sailing is haunted by a problem that, on its face, seems very easy to solve. Many owners have a hard time finding people to go sailing with them and sailors new to the sport have a hard time finding boats to go sailing on. The solution seems obvious.

But it’s not that simple. Some people are just more pleasant to be around on a boat than others, and given the captive nature of a day on the water, neither party wants to be stuck with a dud. A certain amount of trust is needed on both sides of the equation. An owner needs to trust that a new sailor will listen to direction when required and a new sailor needs to trust that they are getting on a boat that is well maintained with a skipper who knows enough to keep them safe. At some point both parties need to just take the leap.

And it’s important that it goes well. New sailors can be turned off for good from a terrible experience on the water, and owners can get shy about inviting people onboard after a few horror stories of new invitees who just don’t work out, and every skipper has at least one.

But it doesn’t have to be that way. Check out these tips to be the skipper that everyone wants to sail with and the new sailor who always gets asked back.

If a crew of experienced and new sailors are all smiling, and owner is well on the way to giving someone a great start as a new sailor looking for experience.

Paul Todd/Outside Images photos

Be a good skipper

1 Check your ego. 

Be confident enough in your own sailing skills that you don’t feel the need to prove anything to invited sailors. There’s no need to rattle off a list of your sailing accomplishments or, worse yet, start rattling off sailing horror stories that you’ve survived. At best you stand a good chance of boring your new crew to tears and at worst you come across as a blowhard that will have them jumping for the dock.

2 Let them know what to expect

Be clear when you’re inviting a sailor aboard for the first time, regardless of their experience, about what they can expect. Are you going out for a daysail and expect to be out for a couple hours? Or have you invited them for a Wednesday club race? 

If they are new to sailing, give them a bit of guidance about what they should wear or bring, without making the list overly long. As odd as it may sound to seasoned sailors, you may need to explain to new sailors that a daysail is not a fancy affair; they should dress like they are going to the park, not like they are going to lunch at a swanky restaurant. And temper their expectations for the weather, lest you end up scrambling for an extra jacket to share when they discover how much cooler it can be on the water.

3 Don’t scare them away 

Imagine stepping on a boat for the first time and being met with a half-hour lecture on safety protocols. You’d probably walk away being either petrified for the highly dangerous activity you were about to partake in or having tuned out five minutes in.

SAILING columnist Nick Hayes has invited dozens of new sailors aboard and is always looking for eager new sailors looking for a chance to get on the water. He balances the safety and potentially scary parts of sailing by keeping it simple and
offering explanations.

“We start with a few simple rules: don’t put your fingers in the winch, keep your head down when someone says to keep your head down, don’t fall off the boat and wear a life jacket in case you do,” Hayes said. “Then we say, it’s going to feel weird when the boat heels, but it’s the way it works and here’s why. I think it’s important to verbalize the why because everyone who wants to go sailing is curious about it.”

4 Give them something to do 

Real sailing isn’t about being a passenger, it’s about being part of the crew. Assign new crew a job, explain to them how to do it, what they are controlling and how it affects the rest of what happens on the boat. 

For instance if you assign them the job of breaking the jib sheet for a tack, talk them through when and how to safely blow the sheet, but also why they are doing it and how the new trimmer can’t trim until they do their job. 

Equally as important is inviting them to ask questions. Let them get a feel for their job and don’t be too quick to jump in with critiques.

If at all possible, invite them to steer, even if it’s only for the trip in from the racecourse. The view from the helm is always the best and there’s no better way to get a feel for how things that happen on a boat affect its performance than steering for a bit. And even if a new sailor doesn’t fully get the big picture, they will leave being able to tell their friends that they steered a boat.

5 Set expectations for next time 

With luck you will have a great sail with your new crew and you’d like to invite them to come back again. They will be far more interested in coming back if you tell them what they might be able to do the next time. 

This is especially helpful if they happened to be onboard for a club race, when the rest of the crew manages a lot of complicated maneuvers without a lot of discussion. Odds are your new crewmember probably didn’t understand much of what was happening and ended up spending a lot of time on the rail.

But if you invite them back and tell them about the role they might play the next time, they immediately start thinking of themselves not as an outsider, but as part of the team. They are already invested.

If they’ll be coming for a daysail, tell them they can steer more the next time, or work on learning about trimming sails.