Sailing guide for beginners

Sailing guide for beginners

The 1×1 of sailing and everything you need to know…⛵

For all of you who have been dying to go on a sailing adventure, there are two ways you can sail off with your TripMates.

First of all you need a sailing yacht. If you don't have a skipper's license (yet), charter the yacht either with a skipper or with a full crew.

Chartering a yacht with a skipper is the best option, because chartering a full crew is the most luxurious and also the most expensive way of sailing. Because a crewed trip means that every little detail is taken care of, even cooking, cleaning, fueling,…and so on and so forth.

Of course, it depends on the size of your group and your collective budget, so maybe a fully crewed yacht is a good option for you! This article will highlight the pros and cons of skippered sailing trips to give you an overview. You can then decide if this way of traveling is for you.

With a skipper


  • with a skipper you don't have to worry about getting a sailing license, getting one is usually quite expensive and time consuming.
  • You have the ultimate guide for your trip. Skippers know the local waters and weather conditions as well as the best places to dock. That means you only have to tell your skipper what you want to see or experience and your skipper will take care of the rest & insider tips.
  • If there is an emergency on board (which unfortunately is not that rare), there is someone who knows what to do in this situation and thus ensures safety. A skipper will make sure your trip goes off without a mess.


  • Traveling with a skipper is most likely more expensive than just chartering a boat, but if no one in your group has a sailing license, then you can't eliminate this cost
  • You have to take care of the skipper's meals, which of course are rather small expenses if you cook for everyone anyway. However, it's good to know this beforehand, so you don't take advantage of the skipper by cooking extra meals. At the end of the day, the skipper is there to make your trip as pleasant as possible, so don't piss him off.
  • If you are looking for intimacy and privacy, then of course a skipper will interfere with that.

House rules

Just like an Airbnb, you don't own the yacht or sailboat. Therefore, there are some rules to make your trip as pleasant as possible. Some of these are basic courtesies and others are very specific to sailing. The rules are there to ensure that the safety of everyone on board is not compromised. Everything is fine until someone gets hurt just because he or she does something stupid that could have easily been avoided. So here are 5 house rules that will come in handy. Undoubtedly, the skipper will give you a safety briefing as soon as you board, but it can't hurt to familiarize yourself with it beforehand.

  1. Safety. To ensure that everyone has a great trip, safety is key. If there is an emergency, everyone must listen to the skipper and follow his instructions, because he is the captain!
  2. The skipper is ultimately responsible for all life on board and always has the final say. Should a situation arise that requires respect, listen to the skipper and don't do what you want to do. This could make the situation more dangerous.
  3. A sailboat is not a toy. Unlike a jet ski, a sailboat has many different components that can be destroyed if used incorrectly. However, you will be rewarded with sunshine and the adventure of a lifetime if you exercise caution and respect the boat and equipment.
  4. All questions are good questions! You should never be afraid to ask questions. If this is your first time on a boat, there are bound to be some things you're not familiar with, so of course you'll have questions. Some sailing terms and concepts can be a bit more complicated and difficult to explain, so if you have big questions, wait for a relaxed moment to ask your questions.
  5. Put things back where you found them. A sailboat moves a lot, constantly heeling and rocking with the waves. Everything on and below deck has a specific place to ensure that the equipment is safely in place. So it's easy to find it again and it won't fall off even in heavy seas. This also applies to your luggage, of course, you don't want your clothes lying around everywhere. So save everyone around you the chaos and have a pleasant trip without quarrels and chaos!

The way is the goal

If you're one of those people who constantly asks when they're going to arrive, then maybe sailing isn't for you! It can happen that you just sail for a day and arrive nowhere. Enjoy the moment and your surroundings, that's what sailing is all about. If you prefer to arrive somewhere, then you should not go sailing.

Wear layers BEFORE it gets chilly

It may seem obvious, but it happens more often than you think – especially when the sun is shining and you're enjoying the weather with little clothes on. The wind can quickly become quite cold.

Top Tip! Go below deck and change as soon as you notice the weather changing. You should always have a hat with you, because most of the heat is lost through the head.

Of course, in the Mediterranean the onion suit is rarely used, but you want to avoid a cold sniffle and it is easy to forget to go below deck and put on a sweater. Especially when you are having fun!

Three sailboats on the water with people

Put something on before you freeze

Storage space is at a premium

This means you shouldn't carry 10 different outfits for every occasion. Also remember that you will most likely have to carry all of your own luggage. So if you have heavy suitcases with you, it can be a hassle. Especially in sunny places, like the Mediterranean, you will most likely only need a variation of T-shirts, shorts and swimwear.

Fanny packs are a good investment when you leave the ship and go to a restaurant or club!

Expect to help with small tasks around the boat as well

Contrary to popular belief, sailing is not just sipping champagne and sunbathing (of course it can be). In general, a sailboat is like a caravan – except that sailing is much cooler, of course. Cooking, cleaning, docking, sailing – all this requires a certain "can-do" attitude. Teamwork makes the dream work, because if everyone pitches in, then mess and displeasure can be easily avoided. If it's always the same people cooking and cleaning, you're bound to be in a bad mood. Be the heroes of the team and volunteer at least once a day to take on less glamorous activities as well. Even if it is not fun, some things just have to be done. The other way around, it means that someone else will take over the unpleasant task next time.

Keep your valuables in a waterproof bag

On a boat things are bound to get wet. Protect your passport and important notes from the water with a waterproof bag and just travel more relaxed.

Barefoot is a good choice

On land you can wear shoes and sandals. It is also important to have rubber soles for your time on deck. No fancy shoes with heels or smooth soles for men or women. You don't need fancy sailing shoes to look good either, but of course bring them if you have them.

Don't forget sunscreen and sunglasses

Just because the sun isn't shining directly on you doesn't mean you can't get sunburned. Even on cloudy days, put on SPF 50+. You are outside all day.

A common mistake made by many people is not wearing sunglasses. A 10€ pair of sunglasses from a local market vendor is not necessarily enough to protect your eyes. Protect yourself and invest in a good (and maybe a little more expensive) pair of sunglasses. This way you can protect your eyes and enjoy the view.

People relaxing on a sailboat in a mountainous scenery

Don't forget sunscreen!

Everyone gets seasick – live with it

Okay, even experienced sailors get seasick once the swell gets stronger and the boat starts to rock. Being seasick feels pretty awful and uncomfortable. Imagine having a pretty bad hangover and then being tied to a carousel. 😣 Seasickness can usually last all day, depending on how strong the waves are – we don't want to sound dramatic, but it will feel like the worst hangover you'll ever have.

Anyway – don't be afraid! Here's how to deal with seasickness: Stare at the horizon when you notice you're getting worse. The horizon is the only stationary point when everything else is moving. It will help your body to reorient itself and you will feel less sick. You can also take seasickness pills if looking at the horizon doesn't help. These pills are taken before you get sick and usually work quite well (but not always) – there should always be some on the boat.

If it gets so bad that you have to throw up – be warned! This phase lasts a very very long time. All you want to do then is lie down and slowly disappear (preferably not into the ocean). Fortunately, seasickness always has a silver lining – once you've been through it, you won't experience it again for the rest of the trip as your body gets used to the rocking.

Sailing helps you escape the digital media

You are guaranteed to get bored on board! so pack a portable (and waterproof) speaker, some books and a game or two. So you will not get bored!

Do you feel like an adventure now? Then check out JoinMyTrip and join a trip you've already planned or simply create your own.

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