A guide for your perfect Sailing Holiday in Greece

The beautiful turquoise, safe waters, numerous islands with spectacular beaches, whitewashed houses and traditional Greek cuisine- just some of the reasons you will want to experience a sailing holiday in Greece, at least once in a lifetime. Though we guarantee you will want to come back.

Why sailing in Greece is the best?

Greece is one of the top sailing destinations worldwide, and unique for the “island-hopping” opportunities.
With 6000 islands (many uninhabited) and a coastline of more than 13.500 km, you will be able to explore new locations with unique characteristics each day during your sailing holiday.  You will also be amazed about all the historical sites that you can visit all around the Greek islands.

The allure of a Mediterranean sailing vacation becomes an unparalleled experience with fresh seafood, relaxing coffees, fruity, light wines. Something you must try at least once in a lifetime.

So get ready to explore the sites of prominent Greek history, taste the Mediterranean cuisine and the Greek island life and sail the magnificent seas.

1. Choose your departure place

No matter which islands you chose you will have a great time. Greece is so famous for sailing that you will find a sailing tour operator almost everywhere.

Decide what you would like to do/experience more and chose your island hopping/sailing trip accordingly.

We have collected some recommendations below, based on our experience. Of course on every island you can find amazing beaches, places to eat and sites to visit. But every island has a different vibe


You like lively islands, with people and bustling atmosphere? Chose the Cyclades, with the well-know Mykonos and Paros islands.

Mykonos, one of the most famous Cycladic islands in Greece, is seductive with its breathtaking views and beautiful colors. There are many beaches to choose from: Agios Stefanos, Vlychada, Kalafatis and Paradise Beach are just a few among them. When you need to relax there’s nothing better than spending time in the main town (Hora), strolling around the narrow streets. You can also enjoy delicious dishes and coffee in cozy small places on every corner. Mykonos is an island for all tastes!You might find these islands a bit less ideal for families with kids, but don’t worry!


If you sail with kids and want something family friendly you can choose some island on the Saronic gulf (like Aegina, Agistri).

You can also plan a one-day or two-days sailing trip from Athens to one of the nice Saronic islands. These short trips are perfect for any type of travellers, and they will give you a taste of the Greek islands’ life. And the kids will not be bored either, since the sailing trips are few hours only. Read further to see our advice abut sailing with kids.

If you decide to visit Aegina for a one-day sailing trip don’t miss the monastery of Nea Moni that dominates the island’s skyline. This Monastery was founded before 1000 AD and has been restored beautifully to its former glory. You will have to take a car or a taxi to visit this place, but definitely worth it.

Oh and don’t miss those traditional tavernas right on the beach or hidden in the tiny little alleys, where you literally feel you are part of the history.

A two-days sailing getaway to the Greek islands from Athens

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If you happen to travel early or late summer and want to enjoy some hiking activities, you can choose Kithnos, Kea or Hydra.

These relatively less-known islands have a unique charming and relaxing atmosphere.

Kithnos is a lush, green island at the northern edge of the Cyclades. The name comes from an ancient Greek word meaning “green”. Kithnos is considered to be one of the most beautiful islands in Greece and was once used as a hideout for pirates seeking refuge from their enemies. You can find many hidden coves along her coastline where you can enjoy some solitude or read your favorite book while overlooking the deep crystal waters below.

Of course, they have magnificent beaches: like Kolona beach on Kythnos, Pisses beach in Kea and Hydronetta in Hydra.


The Sporades Islands (Skopelos and Skiathos being the main islands ) have their own charm as well. These are called green islands, with magnificent views when you sail around them!

There is an abundance of uninhabited territory available for those who want some peace away from civilization’s hustle bustle; surely your captain will take you out there for a few hours so that we can enjoy this beautiful scenery together. We recommend to visit the island of Arkos with the pleasant little traditional taverna right on the sandy beach.

Sailing in Greece- the Sporades. Skiathos and Arkos
The nice little traditional taverna on Arkos island

You will be hard-pressed to find a place on Skopelos or Skiathos that doesn’t have something in common with the world famous movie, “Mamma Mia!”. Did you know they even have boat trips where it’s just you and your significant other?

Last, but not least, of course, Santorini. This charming  island is perhaps on every bucket list however note that you will find crowd from May till late October. 

What would bring you to Santorini? A beautiful sunset, a romantic getaway, or an amazing family vacation. You can experience all three of these and more when sailing around Santorini with your loved ones. You’ll never forget the beautiful Santorini sunset as you enjoy a nice glass of wine from aboard your boat.

You can find many, amazing sailing cruise operators almost on every island, or in the mainland’s seaside settlements  in Greece. Most of them will offer different types of sailing cruises depending on your needs. The best to chose a full day, or a multi-day island hopping trip between the neighbouring islands (to sail the Cyclades islands from Paros or Mykonos,  to visit some uninhabited islands with traditional tavernas, enjoy the sunsets from the boat and many other activities, that only a sailing adventure can offer).

2. Choose the dates

Basically, the summer is very long almost all-around Greece (not the northern parts though).

You’ll find amenable sailing conditions from as early as April to as late as October. We would say the best time to enjoy an unforgettable sailing holiday is outside the peak season in July till August. In May, June and September and October there is a low chance of extreme heat. Planning your sailing vacation outside of the peak touristic months also gives you the possibility to secure lower prices and avoid crowded island.

In May, June, or September, you’ll still enjoy amenable weather and maybe somewhat lighter winds (mostly south).

The temperature during off-season averages between 73F (22C) and 86F (30C).

During the peak season (mostly June-September ) there is a chance for the dry, strong north wind, very well-known by the experienced sailors of the Greek sea,- the Meltemi. Usually, the wind starts in the early afternoon reaching 4 – 5 Beauofort, which is not suitable for cruise sailing.   

But don’t worry. The Greek sailors are the best around the World, and they will know when not to sail, and where to anchor the boat and wait for the right sailing conditions.

3. Sailing in Greece with children

Kids will have so much fun on board of a boat during their sailing vacation. All providers allow children aged 5 or more, and there are many safe activities for them to participate in besides just playing with each other! Skippers will also educate you about safety onboard. Surely you have nothing to worry about, the Greek sailors are World famous for their professionalism.

sailing with kids in Greece

Wherever you sail in Greece you will be mesmerised by this magical land

You will always remember your sailing holiday in Greece, discovering this magical country that has been a mainstay in the Mediterranean for centuries. With its rich history, beautiful scenery, delicious food and friendly people, you will find yourself falling deeply in love with this paradise on earth. And when your trip is over, we hope it leaves a lasting impression of Greek culture from which you can draw inspiration from throughout your life.

If you have any questions about our custom sailboat rental services or would like more information leave us a comment below.

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