Sailing on a 'private' yacht across an endless turquoise sea, wind in your hair, countless islands, undiscovered bays and beautiful coastal towns to choose from and all the freedom to go wherever you want. Sounds like an unattainable far-off show? Then be surprised, because that first step on board is closer than is often thought....

Text & photography: Jules Bijpost

Indeed, the Mediterranean is home to some of the most beautiful sailing areas in the world. Of course, we know the Caribbean as a dream destination, but it is not for nothing that sailors from all over the world have European island hopping at least as high on their bucket list. Especially in Croatia and Greece, this is the way to fill out your holiday.

Culturally, historically and culinarily hugely interesting countries. And islands abound, in all shapes and sizes: from large to small, inhabited or uninhabited, developed and cared for or, on the contrary, unspoilt and pure, idyllic or bustling and always navigable within a few hours. The ideal holiday destination with a sailboat, if you ask us.

Europe vs. Caribbean

Say you are going on a week (or go crazy: two weeks) sailing holiday. Where will you go then? See the pluses and minuses of the two most popular options here.

Self-sailing in the Caribbean


Advantages: Tropical climate so almost always nice and warm, even during the European winter months. Very stable winds, usually from the east around 20 knots (4-5bft). Because of the tropical climate, you will find a colourful underwater world with lots of coral and fish.

Cons: Relatively far and expensive flights. Little choice in rental yachts. Few ports/villages and culture.

Self-sailing in Greece/Croatia

Advantages: Relatively close to home, so easier and cheaper to travel. Lots of choice of sailing yachts. Almost always good weather between May and October. Countless islands within easy reach, with the possibility of visiting cosy villages, boulevards or cultural sites.

Cons: Crystal-clear water, but no colourful underwater world like in the tropics. However, with a bit of luck, you will also 'just' meet dolphins and turtles along the way here. In the winter months it is a lot cooler here, but still very pleasant until early November.

First step on board

To sound out what you really need and where to start in order to be able to sail around here on your own soon, GW spoke to Querijn van Gennep: founder and owner of Portokali. A Dutch company that has been organising sailing holidays in the Mediterranean for many years.

Let's start right away with the key question: what do you need to board such a yacht?

Not much at all! An enthusiasm for water sports and adventurous spirit will probably help, but in fact, anyone can sign up for such a sailing holiday. You don't need to have any experience at all in sailing such yachts.

But of course, such an expensive sailing yacht is not given to just anyone. So then you probably need staff on board?

Haha, no not everyone can indeed bring their own boat. But the requirements are not very high. With a Dutch sailing licence (KVB 1+2) you can already just go sailing. Otherwise, we have plenty of enthusiastic Dutch-speaking skippers who can sail with you. They can then steer the entire ship and take everything off your hands, or just help you with certain manoeuvres and advise you. It all depends on what you prefer. And this way, you can also work on your own sailing skills along the way.

Many people who own a sloop in the Netherlands have a sailing licence. But they can't just take a sailing yacht out to sea, can they?

That's right, sailing at sea is something very different from cruising the canals in a sloop. But we have a solution for that: flotilla sailing. You sail the same route with a group of yachts and a so-called mother ship accompanies you. There are two experienced skippers on board, who brief you every morning on that day's route, the weather conditions, any points of interest, can help you moor and set sail and know everything about the area you are sailing in. So you will constantly have someone around to assist you if needed.

That does sound like some of that freedom will be lost then. Do you then sail all day in a train following each other to the next port?

No way, absolutely not! Everyone is completely free to go wherever they want. Some leave immediately after the briefing at 9.30 in the morning, others go into town before sailing and others go out in the dinghy to explore a beautiful bay and snorkel. So you have complete freedom to do as you please, but you do know that there will be someone to pick you up in the next port and every morning you will hear exactly what to expect along the way and which bays you really shouldn't miss, for example...

And what kind of people are they, with whom you sail in such a flotilla?

This varies. During the school holidays, i.e. July/August but also the May and autumn holidays, these are mainly families with children aged between 10 and 20 on average. But outside, from April to October, we see many (befriended) couples, groups of friends sharing a boat together, but also independent travellers signing up.

Independent travellers?

Yes, they sail along on the mother ship that accompanies the flotillas. After all, there are two skippers on that, but most yachts are for 6-8 people. So there are still a few places available on board. It is great fun to join them and meet new people!

Finally, what is the nicest place to start such a sailing holiday?

Well... There is so much beauty in the world. Still, I would say Greece, especially from Aegina, a small island just off the coast of Athens. Now in fairness, I have to say that I am somewhat biased, because we have our own base and yachts there. But of course that is not for nothing. After all, you fly direct to Athens several times a day from the Netherlands and from there you can reach Aegina in two hours. So you avoid the big crowds and depart from a private jetty on a beautiful island in the middle of a very versatile sailing area... How perfect do you want it.

Want to know more? Then be sure to check out www.portokali.nl