Common Bareboat Chartering Mistakes

Learn from our (and others’) experiences to avoid these chartering blunders

To set us off on the right foot, let’s just say that the biggest bareboat chartering mistake you can make is not doing it at all. Charter sailing vacations, in our opinion, are the single best way to experience new places, share adventures, and really hone your sailing skills. Yes, you need to be a competent (and qualified) sailor to bareboat charter, but there are a lot of ways to still take a sailing vacation if you’re not quite ready to set sail on your own. For today, however, we’re only talking about bareboat sailing charters, where you and your crew won’t have a hired skipper with you.

Behold, our list of the most common bareboat chartering mistakes. Keep in mind that these are just the most common. It never ceases to amaze us the kinds of things we’ve seen in our travels, but a lot of the blunders we see fall into one of these mistake categories.

Preparing and Packing

The vast majority of major sailing charter mistakes happen way before you even get to the boat (which is a little comforting, right?). These are things you are 100% in control of and a little extra planning can solve most of these snags. That being said, a couple of these are vacation-enders, so consider this your fair warning.

  • Not having the right qualifications/experience

    This one is a bit of a sore spot, we’ll admit. There are sailing education companies out there who will have you believe that you can read some books, maybe even take a few 0n-water classes, and then be issued some kind of certification that will allow you to charter a sailboat anywhere in the world. If I could press one of those obnoxious buzzers and say “Wrong!” I would. You can read our entire “Biggest Lie in Sailing” blog post for the whole story, but the short version is that you need documented experience before any reputable charter company will allow you to take one of their boats. At NauticEd, we use an electronic logbook so our students can show charter companies their experience. The NauticEd Software summarizes the student’s sailing achievements into a charter-friendly Sailing Resume. This is a free service to NauticEd Students.

    If you’re unsure, speak with your charter vacation booking agent or the charter company themselves and confirm your qualifications and experience before you make your booking. Be aware here if using internet booking engines. Make sure you are working with an agent who knows the requirements. You should submit your sailing resume in plenty of time before you travel there to really be sure.

    The Mediterranean and The Seychelles

    These sailing regions require a Sailing License. A sailing license is not a certification. The two most accepted Sailing Licenses in these regions are the ICC (International Certificate of Competence) and the SLC (Sailing License and Credentials). No matter who you are or how much experience you have or what and where you have sailed in the past, you simply must (as of 2018) have a Sailing License. But as above, you must also have an adequate sailing resume of experience. This is why the “Zero to Hero – Get Certified to Charter” programs don’t work. If you have a different license, check with your charter agent as to if what you have is adequate — license-wise and experience-wise.

    Nervous? Join a Flotilla

    Being nervous about skippering a sailboat on a sailing vacation is a bad idea. Even if you feel competent, you must also be confident. If you have any hesitations, consider joining a flotilla where you have a lead boat with a competent Captain leader who can help out in areas where you need. NauticEd operates many flotillas throughout the year: See

  • Over or under-provisioning

    What provisions to have on board can be a little tough because you want to have plenty to eat and drink on your vacation, but you also don’t want to be tripping over extra stuff or have food go bad before you’ve had a chance to eat it. Our general rule is that if you’re going to the Mediterranean, go light on food because you’ll have plenty of opportunities to restock or enjoy local restaurants. More remote places, like Baja or Belize have fewer places to re-provision, so plan well before you head out.

    For non-food items, what you need can vary a little, so if you’re bareboat chartering, this provisioning checklist will certainly help. It also covers food basics, but if you’re cooking full meals, you’ll need to mealplan and provision accordingly. In terms of extras that you’ll want to take from home, this blog post about packing for bareboat chartering has great lists, but some of the big ones are making sure you have the right electrical adapters and chargers, your own snorkel and mask, reliable GPS on your tablet, and planning to have a kayak or SUP on board!

  • Choosing the wrong boat

    This one may seem silly, but we always recommend that you chat through with your agent which boat is right for you and your crew. For example, if you have inexperienced crew members (or anyone feeling nervous) or kids, a catamaran is likely the best choice. Your yacht charter agent can really help you out with this – in particular, they can help with knowing if a forepeak shown on the boat diagram is actually a sleepable cabin or not – is it airconditioned or not. While the boat may say it has air conditioning – is that air conditioning only while at the dock or does it actually have a generator to drive the air-cond. while away from the dock.

    As a side note, you can charter a catamaran with only monohull experience as long as you plan well and talk it through with your charter company. Typically, if you have lots of monohull experience on bigger boats, they’ll let you charter a catamaran that’s a little smaller. You’ll probably need to spend a few hours with a local skipper when you get there to make sure you’re comfortable or maybe even hire a skipper for a couple of days. It varies, which is why you should check before you go.

  • Relying on Outdated or Rusty Knowledge

    We know, you don’t want us to refer to your knowledge as rusty or outdated, but what we mean is that there are some specific skills you will need to use on a bareboat charter that you may not use on a regular basis (or have never needed to know before). For example, some of our most experienced team members brush up on their navigational skills in the spring because they haven’t been used in the winter. For the outdated part, we’re talking about sailing education. Teaching techniques should be constantly evolving (at least we sure do!), especially in regards to charter-specific skills, like anchoring/mooring, so even if you’ve been taught some skills before, it might be a good idea to refresh yourself before embarking on a bareboat charter. Can you sail up to a mooring ball if your engine goes out? Can you diagnose simple electrical problems like a breaker keeps blowing or mechanical problems like if the water pump impeller breaks? If the chart plotter goes out, can you plot a course on a chart? How do you derive your heading given that the chart has compass variation? How do you deal with a flooded carburetor on the outboard dinghy engine? We could go on … !

How can you brush up on skills and make sure you have the qualifications you need? Buy purchasing the Bareboat Charter Master Rank Bundle or even individual courses for the skills you’re rusty on. Remember, you’ll get access to the courses forever, so buy it once and then review whenever you need to. You can even take the quizzes to test yourself!

A big mistake is that the skipper is the only one that knows what is going on regarding sailing and managing the boat. For that reason, we have put together a really excellent Yacht Charter Crew Course for your crew to cover fundamentals and important safety and operational issues. Having your crew take this course is guaranteed to take the pressure off the skipper and ensure a safer vacation.

Starting your bareboat chartering vacation

You’re here! Ready to head out! You’ll likely be more excited than you typically are, so this is the best time to move slowly. Do those double-checks, take some breaths, and make sure you’re actually ready to leave.

  • Not listening to your orientation

    When you check in with your chartering company, they will give you a thorough orientation of your boat. Well, reasonably thorough, depending on the company. They may not know exactly how experienced you are with chartering or sailing boats other than your own, so you’ll need to ask lots of questions to make sure that you feel comfortable with the boat you’re chartering. Listen well and pay close attention and take written notes. You’ll be glad that you did. (Pro tip: Make sure you really understand how the waste holding tank works on your boat)

  • Neglecting to check the boat before you leave

    Even reputable chartering companies can miss stuff, so don’t blindly trust that your boat is in perfect order. Before you leave the dock, check all light bulbs and switches, fans, bedding, and confirm that everything they said would be on the boat is actually on the boat. As a side note though, definitely do make sure you’re renting from a good boat chartering company. We have highly knowledgeable chartering agents to help you book sailing vacations and we never charge you a fee to do it, so if you’d like to learn from our experience, we’d love to help. We only ever work with companies we know are good. P.S. there are some companies that are very substandard. You’re spending a lot of money – going with a reputable company is everything.

  • Not “Shaking out the Charter Dust”

    We’ve already mentioned that it’s your responsibility to make sure that your boat is ready for your trip, but we also suggest doing a few things right away to make your trip a little easier. We call this “shaking out the charter dust.” We’d love to believe that every person who charters a sailboat knows exactly what they are doing and is the most tidy, considerate, and competent sailor you’ve ever met (aka. A NauticEd student), but this isn’t always the case. There are lots of things that can lurk within a stac-pac.

    We wrote an entire blog post about how to shake out this charter boat dust before you start one of your longer journeys and we highly recommend reading it, taking notes, and then bringing it with you as a checklist. You’ll thank us when your lines are tidy, your mainsail raises easily, and your reefing lines don’t catch on, well, anything and everything.

While sailing


  • Being a bad leader

    No one wants to sail with someone yelling at them all the time. Especially on vacation. Learning how to be a good leader on a sailboat (and while chartering) can not be emphasized enough. Clearly defining roles is important and then leading in such a way that makes people feel at ease and cooperative will make for a much safer and more enjoyable trip. No one gains anything when you make your crew feel stupid or like they’re in a bad corporate meeting. If you’re interested in hearing about one of our own learned from his mistakes, read How to be a good leader on a sailboat.

  • Communicating poorly

    This mistake isn’t reserved for the skipper only. Yes, of course, the skipper needs to communicate clearly and confirm that the crew understands their instructions, but if you’re crew, you need to also communicate your own expectations. Ideally, you’ll have a good mixture of people on your boat, both in experience level and sailing interest. Talk through what everyone expects of the trip. If someone is happy to help sail when needed, but is hoping to relax on this trip, make sure that happens! If someone is super eager to learn and is inexperienced, make sure that they get some good instruction time!

  • Waiting to teach your crew helpful skills

    Speaking of crew, we always suggest teaching your crew how to tie knots, handle lines, and throw a line ashore effectively. Make a game out of it! You’ll be glad for the help during the trip. That being said, we also recommend/insist that the skipper checks those knots, even if it seems like someone knows what they are doing.

    (If you want your crew to REALLY have a leg up, we suggest the Yacht Charter Crew Course)

  • Checking and re-checking

    The skipper is responsible! That is a universal truth. So if the line tieing the dinghy slips loose and the dinghy is lost – the skipper is responsible. If the mooring line slips off the mooring ball in the night and the boat washes onto the rocks – the skipper is responsible. If the anchor does not hold, if the dock lines are not tied properly, if the fenders are lost, if – if – if…

    But that is not a release of duty to anyone because on a charter – everyone pays the share of the financial cost no matter who is responsible. However, some situations have dire consequences. Thus the skipper or a designated boating competent person must be the person responsible for checking and re-checking every line, every knot, everything, everywhere, always. It is unfair to assume that a crew member has done their job properly when this is possibly the first time they have ever done it.

    There are literally hundreds of things to check and notice as you go. Something as simple as checking that the outboard engine is properly tightened onto the transom of the dinghy is crucial. Believe us on this one – one time it was the charter company themselves that did not tighten it on. At one point we looked back and saw us towing the dinghy and the dinghy was towing the outboard (now the overboard-outboard) by the safety line.

    Importantly, the skipper must check the anchor throughout the night. Set an anchor alarm to alert drift – set a timer alarm to do a visual check.

    Check – Check – Recheck Everything, Everywhere, Always!

  • Maneuvering Skills

    Expert boat maneuvering skills in tight quarters is a must. You also must be confident at backing a boat into very tight spaces in a marina. This should not be your first rodeo and practicing in the marina on the vacation is the last place you should do this.

    Not so skilled? No worries – take the NauticEd Maneuvering Under Power course. In the course, there are dozens of exercises with explanations on how to maneuver a sailboat in a tight marina with various cross-wind directions.

Well, that covers some of it! Sailing a new boat, while exciting and fun, can also mean a few mistakes. The excitement of the trip can cause great sailors to forget things they’ve never forgotten before or make silly errors. We cover, in-depth, how to be successful with bareboat chartering in our Bareboat Charter Master Rank Course Bundle. We highly recommend taking the time to not only learn everything you need to know about chartering and the skills required to do it well, but also gain the documented experience to be allowed to charter a sailboat internationally. In our minds, the Bareboat Charter Master Rank Course Bundle is the only way to guarantee you have the competence and qualifications to bareboat charter.

I find myself drawn to any project that allows me to learn and use my creativity to solve problems - and sailing tops my list!
Trisha Evelyn
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Last updated on August 27th, 2023