How to be a Great Crew Member on a Sailing Vacation

And Have a Great Time

Photo Courtesy of Beneteau

by Grant Headifen
Global Director of Education
NauticEd International Sailing Education

So, you’ve been invited on a sailing vacation with a friend or family member – what now? Well first off, say yes – Ok got that one out of the way – moot really because you would not be reading this if you had said no or maybe.

I’ve been fortunate! I have been on dozens (and dozens) of weeklong or 2 week sailing vacations all over the world. I keep going back every year sometimes twice or three times because I love it so much. A sailing vacation with a friend can be the best thing ever and can really form stronger bonds and create everlasting storytelling with lots of laughs. Or, it can go really bad depending on a lot of factors (mostly human).

This article is written for the crew BUT it is for the skipper as well – so both take note!

SKIPPERS – you will be well served to send your crew members to this page. CREW – you are well served to ensure you and your skipper have communicated on these topics. Consider this document the Skipper (or organizer) / Crew contract that can only be adjusted by an email confirmation of the adjustment. This sets things straight from the beginning and puts you all on track for a great time together.

So let’s call this document the NauticEd Standardized Crewing Contract for crewing on a sailing vacation.


Crewing on a Sailing Vacation – Ground Rules

Let’s get some ground rules out of the way first and then focus on the good stuff.


Let’s set it up so that there are no arguments over money. Expectations upfront usually fix that. Money arguments suck!

The Boat Cost

Unless otherwise stated, you’re expected to pay your share of the boat rental and other expenses. There is some wiggle room depending on the cabin sleeping situation. If you’re stuck sleeping on the couch in the salon then you’ll probably pay less than those who have their own cabin. Sometimes there is a forepeak which is decent enough for sleeping but you probably should pay a little less for that situation as well.


When the organizer of the adventure books the boat, they must pay a deposit of anywhere from 30% to 50%. Then about 2 months before they must pay the balance. If you’ve said yes then here are the ground rules on that. Since the organizer signs a contract and is committed to going, you are now committing to your full share of the boat cost regardless of how much you have paid as a deposit. You can’t just say 1 month before “oh just keep my deposit, I can no longer go”. If you do that your friend/organizer is on the hook for the second part of your share. That is so unfair.  Of course, it is standard practice that if they do find someone else to replace you at full cost then you can be off the hook but until then, there is no money back and you still have to pony up the balance. And of course, accidents and life events happen, but that does not relieve you of other responsibilities. You still have to make your car payment and mortgage payment so why are you relieved of the commitment to your friend? You’re not.


It’s a big payment sometimes $2000-$3000. Just be courteous to your friend and pay your share on time. The due dates for payments are hard dates required by the yacht charter company. Don’t stress your friend out taking time to make your share payments.

Cancellation Insurance

You can buy cancellation insurance either for medical reasons or for any reason (any reason is more expensive). Just search Google for “best cancellation insurance” and a dozen companies will come up.


Unless otherwise stated, you are to pay your fair share of the food and libations bill. The food and booze bill for provisioning the yacht can amount to a decent amount and throughout the week there are always incidentals to add. Managing who paid for what can be a real pain in the stern. But there is the coolest most simple App solution called Cost Split on iOS and probably an equivalent one on Android. With the Cost Split App, you enter everyone on the trip and everyone gets an invite to the App. Then whoever goes shopping just makes the entry and can also enter who is partaking in that expense. For example, maybe half of you the crew are strolling down the quay (pronounced key) and you all decide to get gelatos. One can pay and make the entry only tagging those in on the gelato. Maybe one person on the boat is alcohol-free – well for all the boose that is purchased that person is left off that purchase. Try it out – it is the total solution for sharing expenses like this. At the end of the week, it produces a report on who should pay who to equalize everything out. It’s awesome. Just get it. There is a free version but we recommend the $5 version because that is the sharing version.


Sometimes there is going to be loss or damage. It is the nature of boating. The boat will be insured BUT there is still to deductible to pay. The deducible can be anywhere from $500 to $5000. It is up to the organizer of the trip to disclose the deductible to all the crew members. The skipper will have to authorize their credit card and if there is damage or lost items the amount will be taken from the skipper’s credit card.

Almost more often than not, things do get damaged and things get lost so don’t think that you’ll just be careful and not address this topic.

It is pretty unfair that the skipper be the one responsible for any and all damage to the yacht – even if the skipper was driving the boat. Things happen. So the rule is everyone pays their share of the damage (up to the shared amount of the deductible).  For example, when steering the boat into the dock the boat bumps into the dock, a fender rolls up over the dock and a jutting out nail puts a giant scratch in the gel coat – $300. Who pays? The skipper was driving the boat – but who tied the fender too high? Who was sitting on their ass not helping – maybe more help could have prevented that. i.e. everyone pays. A wind gust comes up in the night and blows the cushions off the boat – lost. Who pays? Everyone.

An exception would be irresponsible behavior (called gross negligence in the courtroom). Smoking burns a hole in the cushion – smoker pays. Drunk dinghy driving causes damage to the dinghy engine propeller (or worse) – drunk pays.

Big Group Dinners Out

If you’re the type of person that orders the lobster because everyone is splitting the bill, then shame on you. If you order the lobster because you like it then in that case announce that you’re throwing more into the kitty than everyone else because you’re ordering the lobster. Also,  keep in mind that cost split has the ability to assign more and less to certain people in a group setting like this. The standard rule here is to pay more or pay less than the total average based on what you ate and drank. That is pretty much a good rule for life – everyone knows you ordered the lobster. And they will always question – did you order it because it was the most expensive and everyone was sharing or because you like it. They will assume the worst and the bad taste in their mouth won’t be because they had the cheap tacos instead.

Medical Bills

Difficult one but usually the hurt person pays (make sure you have insurance). Accidents happen. Cavemen never sued anyone because they stepped in a pothole.

Late Arrival Due to Airlines

The boat is usually rented for 7 days which is really 6. Pick up on Saturday afternoon and get back to the dock on Friday night to depart on Saturday morning. Plan on arriving a few days before the charter to explore the local village and area. This also allows your bag to catch up when they are delayed (when not if). If you make the decision to arrive right before departure then you are also taking the responsibility for late airlines. You can not expect everyone else who also paid substantially for their vacation also to wait for you. The boat is leaving. You can always catch a ferry or private water taxi to where the boat will be. Sailboats don’t go that far on the first day, so you can easily catch up. Maybe you can even catch a land taxi to the bay where the boat will be.

Take the NauticEd Online Yacht Charter Crew Course

Learn how to operate the dinghy, learn how NOT to hurt yourself, learn the ropes, learn how to actively contribute as a crew member, learn about all the systems on the boat


Everyone thinks they are a great leader and so for us to say “Be a good leader” to the Skipper reading this will go right over their head. What is a good leader? This article can not lay out all the skills of leadership.

Instead, Skippers – you’re advised to read a leadership book, and here is one of the best. Lincoln was known as the guy to lead by example but he also had many other leadership skills.

As a Skipper you want your crew to say this at the end of the week – “I didn’t think you were leading us, everything just seemed to come together automatically like clockwork during the whole week.” That is the best compliment you can ever get. Crew members, you are not exempt from leadership. Other crew members are watching you and following your lead. You also should lead by example. You want others saying this – “Can you please sail with us again next year you helped out so much. You helped make the boat and everyone gell together. This was the best week ever.”

Everyone (skipper included) should be helping to make dinner. Get up off your ass and help tie fenders and dock lines when coming in. Make a surprise afternoon snack on a big tray for everyone while under sail then take it around the boat offering it up to everyone. Wash down the boat in the morning. Beat everyone up and make the coffee – beat the last person the morning before. Wash the dishes, fetch drinks, tie lines, tidy things away. If you are that person, everyone will follow you. And here’s the deal – do all that and you will get invited back again. Sit on your ass and complain you won’t be invited again. In particular, I have a friend that could never be the skipper of a boat – he just does not have the spacial awareness about him to skipper, but he is the first to be invited. Even one time with a broken foot on the boat (another story) he was getting up with his crutches and washing dishes – dang! You lead by example. And just to reiterate to the skipper here, your job is not to steer the boat and then sit back and have others wait on you because you’re the skipper – “oh such a hard day I had – steering the boat – it was so stressful – wait on me please – bring me drinks – do the dishes”. If you’re that skipper, then guess what? Your crew will not return next year. You’ll be a lonely skipper in charge. They’d rather hire a professional skipper because you’re not a skipper – a skipper leads by example.


Spellcheck doesn’t like this word. It probably isn’t a word but it should be. Being a good follower is a skill. A typical situation is where two experienced skippers are on the boat – but technically one is the skipper of record. You’ve heard the saying “too many cooks in the kitchen” – on a boat there can be too many cooks in the galley and too many skippers on the helm. Surprisingly, this can cause real issues with resulting spoken or unspoken drama. You have to ask yourself what really matters here. A good time for all on a vacation bonding well or; the carrots sliced longways instead of crossways,  sail on this side of the island or that side, tack now or in 5 minutes, dock to port or starboard. Y’all gotta learn to let it go – it doesn’t bloody matter mate. Skipper – listen to your experienced crew, they might have a really good idea – and even if it is not, let it go, give in a few times  – bet a beer on it instead of having to do it your way which is always the right way – follow your crew sometimes. No one is there to prove anything – let it go. Experienced crew – offer suggestions but let it go – maybe your way is better but is that more important than the relationship? Skipper – don’t pull rank. If you have to pull rank, you’re a bad leader. Leaders are leaders because they lead by example. A boat full of friends is a democratic micro-society. Democratic societies still have a leader but they get voted out when they prove themselves to be not worthy. For myself as the leader of the boat, I give myself the role of the servant to everyone on the boat. I’m there to ensure everyone has a great time. It’s my form of leading by example. I gave up trying to prove to anyone that I’m a great sailor many (many) years ago. I just don’t need to “prove” anything anymore. Perhaps that comes with wisdom, confidence, competence, and the realization that the need to prove achieves the opposite. “The proof is in the pudding” they say.

From The proof is in the pudding is an expression that means the value, quality, or truth of something must be judged based on direct experience with it—or on its results. The expression is an alteration of an older saying that makes the meaning a bit clearer: the proof of the pudding is in the eating.

That is such a great round-up quote for this topic. The proof of you being a good skipper leader/follower or a good crew leader/follower is in your actions.


Good skippers don’t always steer the boat, it is the crew’s vacation as well. If they want to steer the boat let ’em. In fact, offer it up. A skipper is not a dual role name for helmsperson. A skipper is the leader of the boat. How can the skipper pour the drinks and make trays of snacks when he/she is always hogging the helm?

Crew Members – if you want to steer the boat – ask! If there is some tricky navigational situation, then the skipper decline at that exact moment.


People that yell never think they are yelling. If you are told you are yelling – you are yelling! Stop it.

Did you know that being yelled at actually prevents the human brain from normal operations? Classic deer in the headlights situation. Even yelling clear instructions will not work. You only make the situation worse. Use your inside voice!

Exception: obviously the ‘inside voice’ doesn’t work if the engine is loud or it’s windy, especially when speaking into the wind. Simply set the expectation beforehand that if speaking loudly then it’s to be heard, not yelling…  Or call it your “outside voice”.

Be Nice – Have Fun

Double Your Niceness – Double Your Effort

It is incredibly difficult to confine 8 people into 400 square feet (40 sq. m) for a week. So you have to double your niceness and double your effort. This is a sailing vacation for everyone on the boat. Everyone paid a lot of money to join. Their expectations are to have a good time and a good time only. Like people that yell, people with drama don’t think they have drama. If you are told you are being dramatic – you are being dramatic! Stop it. Lest you will not be invited back. At worst, like in the tv series Survivor, you can get voted off the boat. And take note, we actually did that once. About midweek after many talks with a crew member to stop the drama, we dropped her at the ferry dock and said goodbye. And never to be invited back again. Try it out, just for a week – be overly nice, overly helpful, and say overly nice things (genuinely).

Round Table Nightly Discussions

Annually, my family, siblings, siblings friends, friends of siblings friends, inlaws and God knows whoever can drag themselves out of a swamp all go beach camping. We call it camp-run-a-muck. Because anything and everything happens. What keeps everyone coming back and still loving each other afterward is the nightly “Kangaroo Court”. It is done in a comedy roasting format. There is an elected judge for the night who wears a silly wig. The idea is that the judge hears a claim, takes evidence (hearsay is allowed), exaggeration is encouraged, lies are entertained and considered for credibility, and finally, the judge issues orders and fines which usually entail doing the dishes, trash take out, camp clean up, making breakfast or whatever needs to happen chore wise around camp. On a boat, swabbing the deck could be included. As injustice as they, no one argues with the judgments passed and everyone gets a huge laugh. One time we even fined the boat skipper for not providing fish for dinner. Try it out – it might work to gel the crew. Also, note that the judge is advised not to issue such outrageous orders because he or she will not be voted in the next night and maybe overly picked on by the incoming judge. Comedy however is essential as is the silly wig.

Be at least, a little bit knowledgeable

NauticEd makes available an online course called the Yacht Charter Crew Course. This course is the perfect course for Crew. It is going to give you a lot of safety information, a lot of how-to’s, and some really great ways that you can increase your own enjoyment of the trip. You’ve paid thousands in flights and your share of the boat. Make those thousands count for more when you have the knowledge of how not to get hurt and how to contribute as a great crew member.

Take the NauticEd Online Yacht Charter Crew Course

Learn how to operate the dinghy, learn how NOT to hurt yourself, learn the ropes, learn how to actively contribute as a crew member, learn about all the systems on the boat

Final Notes

Skippers – send this blog article to your crew members

Crew – send to your other crew members and your skipper.

Now you can focus on enjoying your vacation with no financial tiffs, boat drama, accidents, or leadership/followship issues.

Oh and did you know that NauticEd is also a Sailing Vacation agent for all yacht charter companies worldwide? We don’t charge you a fee – we can give you advice on just about every location in the world because chances are we have been there. We also ensure that you are getting the absolute best deal on your boat because we search the entire world’s database on available boats.

Book Your Next Sailing Vacation through NauticEd

Search for a topic.
My vision for NauticEd is to provide the highest quality sailing and boating education available - and deliver competence wherever sailors live and go.
Grant Headifen
Tags: ,
Last updated on December 31st, 2022