Sailing Trip Guide for Beginners

by | Jun 10, 2022 | Activities, Sailing, Travel Guides

Everything you need to know for sailing 101… ⛵

For anyone looking to go on a sailing adventure, the first thing to know is that there are essentially two ways to get yourself and your travel mates on the water. 

Firstly, you will need the yacht. Assuming you don’t have a skipper’s license, chartering a yacht typically comes in two forms: chartering a yacht with a skipper and chartering a fully crewed yacht. 

Chartering a yacht with a skipper is most likely your best option, as chartering a fully crewed yacht is the most luxurious and expensive way of sailing. A fully crewed yacht means every aspect of the trip is handled by the crew, such as cooking, cleaning up, refueling, etc. the list goes on and on. 

Of course, depending on the size of the group as well as the collective budget, a fully crewed yacht might be out of the question. We’ll break down the pros and cons of chartering a yacht with a skipper so you can make a decision that is in line with your budget, sailing experience, and hopes for the trip! Let’s go!

With a Skipper 


  • Having a skipper eliminates the need to get a skipper’s license, which is relatively expensive and time-consuming to acquire. 
  • You have the ultimate guide for your trip. Skippers know the local waters and weather systems as well as all the best places to dock, meaning all you have to do is tell them what kind of a trip you would like, and they can then further help with planning your itinerary. 
  • If there is an emergency (which is not uncommon), someone on board can deal with the situation, ensuring safety and that the trip goes smoothly. 


  • Having a skipper would be more expensive than just the yacht charter. However, this is an unavoidable cost if no one in your group has a skipper license.

  • You will need to cover the skipper’s meals during the journey, but this is a rather minor expense, if, for example, you are already making meals for five or more people. However, it is good to know beforehand that you don’t try and stiff the skipper by preparing separate meals, which are considerably cheaper than the groups’ food. At the end of the day, the skipper is there to make your trip enjoyable, so you want to keep him as happy as possible. If you’re looking for intimacy and privacy, then having a skipper might impede on you

House rules

Just like an Airbnb, the yacht does not belong to you. Therefore, to make the trip as enjoyable as possible, a few house rules need to be adhered to. Some of them are a common courtesy, and some are strictly sailing-related. It is important to keep in mind that most of the house rules are chiefly in place to ensure the safety of everyone on board. Everything is fun and games until someone gets hurt doing something silly that could have easily been avoided. So, with this in mind, here are 5 house rules that will come in handy. No doubt the skipper will give a safety briefing for you and your travel companions once you step onboard the yacht, but there’s no harm in knowing them beforehand!

  1. Safety. To ensure that everyone gets the most out of the trip, safety comes first and foremost. In case there is an emergency, all aboard must listen to and obey the skipper, who is also the captain onboard. 
  2. As the skipper is ultimately responsible for the lives on board and always has the final word. If there is a situation with a need for caution, please don’t choose not to listen to the skipper, as they don’t play around when a situation is heading in a potentially dangerous direction. 

  3. A sailboat is not a toy. Unlike a jet ski, a sailboat has many different components that, if used incorrectly, may cause damage to the boat or yourself. However, like a jet ski, if you proceed with caution and respect the boat and the equipment, you will be soaked, sun-kissed, and living your best life. 
  4. All questions are good questions! Do not by any means be afraid to ask questions. If you’re on a boat for the first time, there is a lot of things that you will be unfamiliar with, so questions will naturally follow. Some sailing terms and concepts tend to be rather complicated and long-winded to explain, so if you have some “bigger” questions, perhaps leave them for a chilled moment. 
  5. Put things back where you find them. A sailboat moves around a lot, heeling constantly and rocking with waves. Everything on deck and below deck has a designated spot to ensure that equipment stays safely stored in the correct place, so it is easy to find again and that it doesn’t fall once the boat starts heeling. This also applies to your luggage, you don’t want all your clothes, sunnies, and goggles lying all around your sleeping quarters. Save yourself and your traveling companions the mess. 

It’s the journey, not (necessarily) the destination

If you are one of those, “Are we there yet?” people, sailing might not be for you. Depending on your itinerary, you might be sailing for a whole day straight. Being able to enjoy the moment and appreciate the surroundings is what sailing is all about. However, if you’re more into instant gratification, you might want to consider a different type of holiday.

Remember to put on layers BEFORE you get cold

This might seem obvious, but it happens more often than you’d believe – especially when the sun’s out and you’re in minimal clothing, just enjoying yourself. The wind chill factor is real! 

Top tip! is to go below deck and fetch some warmer clothes as soon as you see the weather taking a turn – beanies are great as most of your body heat is released via the head. 

Of course, if you’re in the Mediterranean during the summer, then putting on layers will be obsolete. However, avoiding cold sizzles is something everyone can relate to, and going below deck and fetching some more layers can easily be forgotten.

Three sailboats on the water with people. Sailing trips are special
Put on layers before you get cold!

Storage space on a yacht is limited

This means don’t bring 10 different outfits for every occasion. Keep in mind that you will most likely be carrying all of your luggage at some point, so if you pack a whole suitcase worth of wardrobe, you might struggle a little. If you’re heading to a sunny location, you will most likely be wearing a variation of t-shirts and swimming bottoms.

Fanny packs are a good investment for when you head off the boat to a restaurant or club!

Expect to help with menial tasks around the boat

Contrary to popular belief, sailing isn’t just sipping champagne and tanning (of course, it can be). You can think about it like this, a sailing boat is essentially a caravan on the water – except sailing is much obviously cooler. Cooking, cleaning, docking, and sailing all require a certain “can-do” attitude. Everything that you want to do needs some action on your part. Teamwork makes the dream work. If everyone helps out with everything, then mess and resentment can be avoided. If the same people are eternally cooking and cleaning, it will soon lead to a resentful situation (imagine three meals a day). Be a star and volunteer at least once a day to do some of the not-so-glamorous aspects of life on the water, it may not be fun, but these things must be done, and your travel companions will appreciate you – it also means that next time there’s an unpleasant chore to be done, it won’t be your turn.

Keep your valuables in a waterproof bag

On a boat, things get wet; you don’t want your passport wet or to have to spend time on your holiday drying notes. 

For the footwear aspect, barefoot is usually good depending on the weather

Sandals and shoes for walking once you get to shore. Important to wear rubber-soled shoes to avoid scuffing the deck. So this means no dress shoes for men and no high heels for women. There’s no need for fancy dock siders (sailor shoes) unless you already have them or want to look the part! 

Sun Screen and sunnies (actual sunnies)

Just because the sun isn’t directly shining on you doesn’t mean you are receiving UV rays, even on an overcast day. If you spend the whole day outside, you will need sunscreen – 50 SPF should do the trick.

Now a common mistake people make, not just on sailing trips but in real life as well, is not wearing proper sunglasses. Believe me when I tell you that the 10-buck sunnies 🕶️ you found at the local market just before embarking on your trip is not going to cut it. The fact of the matter is, these cheap sunnies, which are non-Polaroid glasses, are damaging your eyes more than anything. You may think you scored some cool sunnies for cheap, just as you remembered that you’d need them for your upcoming trip. However, the only thing these sunnies achieve is making you look cool! Be kind to yourself (and your eyes) and invest in some proper Polaroid sunglasses.

People relaxing on a sailboat in a mountainous scenery. Go on a sailing trip.
Wear your sunscreen!

Seasickness. It happens to everyone – live with it. 

Okay, so seasickness is common even with experienced sailors, once there are a lot of swells, and the boat starts moving around. The sensation of being seasick is rather terrible – imagine a really bad hangover, and you’re tied to a revolving carousel with no way of escaping. Seasickness can often last a whole day, depending on the severity of the waves. Now I don’t want to sound overly dramatic, but it is probably equal to one of your worst hangovers. 

However, fear not! There are ways to avoid feeling this awesome sensation for those of us who aren’t too open to trying new things (your loss!). Firstly, when you start feeling the sensation of seasickness coming on (it’s similar to motion sickness one might experience in a car), your best bet is to start staring at the horizon. This is because the horizon is the only “stationary” point as the boat and everything on it are moving with the waves. Staring at the horizon helps you reorientate yourself, and you should start feeling an easing of the dreaded seasick feeling. Secondly, if staring at the horizon doesn’t help, the next best thing is seasickness tablets. These tablets can be taken before you even feel any symptoms of seasickness and usually work really well (but not necessarily) – the boat should always have some on hand.

Now for those of us weak enough to experience the vomiting stage – be warned, it lasts a long long time. All you will want to do is lie down and slowly disappear. Thankfully, there is a silver lining to seasickness – once you go through it, you won’t experience it again during the same trip as your body becomes accustomed to the motion. 

Sailing offers an escape from the constant bombardment of digital media

So with this in mind, boredom will strike. A portable (preferably waterproof) speaker, books, and cards are good pastimes. 

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