• Dream vacations in Greece
    with a sailing yacht

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  • YachtSailing in greek islands
    is easier than you think

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  • Every Greek island has its own history!
    discover it with our yachts.

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  • Welcome to Yacht Sailing in Greece

    First time sailing? Hire a skipper and cruise the Greek islands with style and safety!
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Booking a Yacht has never been easier

Decide when

Choose your dates! Remember that the departures take place on Saturdays and we operate on a weekly basis.
Hint: The earlier you decide to come the cheaper your air tickets may be.

Check availability and Select Boat

What is the most suitable boat for you? How many guests will be visitng? Would you prefer a monohull or a catamaran? Do you require air conditioning? Select among various yachts and book according to availability.

Let us do all the rest!

Vacation planning is not an easy task! That is why you need to rely on professionals. Experienced trip planning, 24/7 support during your stay in Greece. Hundreds of successful reviews for a unique vacation experience!

We are your Friend in Greece


H!, My name is Eugene! Let's select together the best yacht for you and plan efficiently a unique vacation experience. Feel fee to ask anything you wish!


Hi, my name is Maria. I will answer all of your questions concerning your imaginary vacation in Greece. Feel free to contact me for anything you need.


Hi, my name is Dimitris. I am responsible for our technical department and for all the technical issues of the boats and support during your trip.

Let's plan your vacation together!

Trip Planner

You have reasons to Trust us

Why Us?

  • Because of what YOU say about us!
  • Hundreds of successful reviews
  • Certificate of excellence in TripAdvisor
  • Verified by the Greek National Tourism Committee
  • Not another mass charter agency
  • Unique trip planning for each guest
  • Real photos and videos of the yachts advertised
  • We are owners of the sailing yachts we charter
  • All our yachts are certified by the Lloyds Registry
  • Representatives in 99% of the Greek islands
  • Our knowledge for Greek islands is unique
  • Trip Planning for cruising the greek islands 
  • 24/7 help during you sailing holiday
  • Better bareboat yacht charter prices


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Why Sailing?

  • No other way to meet Greece so efficiently
  • Discover awe inspiring scenery
  • Explore hamlets, villages untouched by tourism
  • Meet Greece as a real traveler
  • Wake up and dive in azure and turquoise waters
  • Great value for money
  • Meet the Greek islands
  • Taste amazing cuisine
  • Cruise in amazing places and nature highlights
  • Swim in magical isolated locations of Greece
  • Explore different Greek island each day
  • Unique island hopping
  • Personalized yacht sailing cruises
  • Embrace the Greek sailing culture



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We were dealt a Royale Flush on the Casino Royale catamaran in the Greek islands. Yachtsailing.gr made the transition from our hotel to boat a breeze by Eugene and his staff. We got greeted by our Captain Haris and our Hostess Vicky with a very warm welcome. They were very informative and accommodating from the get go. Their was nine of us renting the very comfortable catamaran, The Casino Royale. Each day Captain Haris took us to a beautiful spot to eat a fabulous Greek lunch cooked by our Hostess Vicky. Every morning we woke up to the smell of fresh coffee and a hot Greek breakfast. Each night we’d dine at whatever port we sailed to. Captain Haris was very entertaining and shared some great stories of his sea experience. Vicky, our hostess was an amazing Greek family style cook. She took great attention to pleasing everyone’s needs and was kind enough to share her recipes with me. By the end of week we all felt like one BIG GREEK family. All nine of us agreed we were so happy that we chose to have a Captain and Hostess because it made it truly a vacation. Haris and Vicky took care of all the connections and knowledge to navigate this trip. It was a trip of a lifetime!

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Tripadvisor member - 786suzyk

Excellent service made for a wonderful trip.

We returned a week ago from a 6 day trip on the Poker Face catamaran. It was wonderful. There was great communication from the beginning with Eugene and we felt like he worked with us on the price and listened to what we wanted in a boat. Once we arrived, we were thrilled with the catamaran. It was roomy, and had areas both in the sun and shade that we could hang out it. Our captain, Thodoris was the consummate professional. He sat down with us and we determined out itinerary together. He suggested a place that we had never heard of, and it ended up being off the beaten track, and the highlight of our trip. He worked hard to ensure our comfort, even moving the boat one evening to reduce wave action, and changing out the mooring ropes so that the noise at night was reduced. There were only three of us on the yacht, but we felt the price we paid was very reasonable. It was such a treat to have it just for our small family. My only suggestion is that you really don't need to bother with getting groceries ordered ahead of time. Each island will have grocery stores near the docks, and you can get whatever you want, without waste. It was very easy to get the provisions, as well as find great, reasonable restaurants nearby. Eugene met us upon our return to ensure everything was great on our trip, and it was. We hope to sail with this group again in the future.

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Tripadvisor member - KatyMC18

Wonderful trip through the Greek Islands

We just arrived back to Athens with several friends from a week sailing on a 50 feet Catamaran “Casino Royale”, our skipper Haris Psaropoulos and the hostess Vicky did an excellent job spoiling us during the complete week!! What an excellent ride! Even though the captain recommended several programs for the week we insisted on going to Mykonos, man was he right on all the things he told us about that island! Next time I would recommend all others to trust 100% on the captain recommendations! He was right about everything!! Very honest with all the things he told us! The Greek food Vicky prepared for us several days and all the little bays we visited during the week made this trip simply unforgettable!! 100% recommendable!!! Looking forward to come back with them in the future!

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Tripadvisor member - Flyer784824

Best trip ever! Sailing in the Saronic islands

This trip was incredible - I can't imagine doing anything else on our visit to Greece. Our skipper, Joe, made the trip legendary with expert knowledge of the area and safe sailing between the different Saronic islands - would highly recommend Joe for your trip. Our days ranged from swimming, sailing, and exploring islands with frequent stops for standup paddle time and other activities. This company is more of a boutique with about 25 boats all very well maintained. Eugene and the other staff were very helpful throughout the planning process and the trip itself. Will definitely come back as soon as we can - there is so much to see!

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Tripadvisor member - JamesH5502

Amazing trip on the Poker Face with a great skipper!

We had an incredible trip over the past week on the Poker Face catamaran. Our skipper - Theodore - went above and beyond to make our voyage extremely fun, relaxing and memorable. We visited the islands of Hydra, Paros, Kithnos, and Siros - it was a ton of fun. From the very start the team at YachtSailing were extremely professional and accommodating. Theodore put together a fantastic itinerary based on our preferences, and kept a keen eye on the changing weather. One note: when ordering food ahead of time, make sure to confirm quantities as they tend to buy in kilos and not individual items (so 3 carrots actually means 3 kilos of carrots!). Overall, couldn’t recommend this trip any more. Amazing boat, fantastic crew, and beautiful sights. We’ll be back!

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Tripadvisor member - eldanilovz

Greek Vacation, Thoughts of a local.

How well do you know Greece? Greece is the southest part of Europe and a member of the Euro zone. The capital of Greece is Athens, which is well known for her historical sightseeing due to the endless cultural civilization of the ancient years. Practically this means that if you are a fan visiting museums, historical places and cultural pieces of art Athens is the No1 destination for you. Although I come from Athens and I am used in the everyday life and activities every time I find something...
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Weather in terms of Sailing in Greece!

WIND IS THE 'ENGINE' OF SAILING Weather in Greece is mostly calm and easy to predict. We are a country well known for the high winds coming from the North known as 'Meltemi'. In general summer in Greece is quite hot. Starting from May when wind is more suitable for sailing with an average of 15-22 knots of wind most of times seen our wind meters. June and mid of July will be a bit more windy but still it will be pleasant since wind speeds would be from 14-27 knots. Of course no one can predict...
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Sailing for one week in Cyclades Route Suggestion 1

Sailing in the Cyclades area requires normally a minimum of 2 weeks time. In the opposite case where your sailing time is limited you will need to cover a lot of miles in one day. Mainly our suggestion for these kind of distances is to try to make a middle stop for a swim and end to the port of destination at the end of the day. For 1 week sailing we suggest 3 different routes deppending on the weather and the crew (if they have been here before or not). See below our suggestion: Saturday: For...
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Special Offers

Special Offer

'VEGAS' - Lagoon 420

Refitted in 2018! Enjoy your sailing vacations with all of your home amenities together on
From: 20/05/2019
To: 20/05/2019
Special Offer

'JOKER' - Beneteau 50.5

Refitted in 2018! JOKER is considered one of our most popular yachts according to our guests!
From: 20/05/2019
To: 20/05/2019
Special Offer

'ROULETTE' - Beneteau 50.5

Refitted in 2019! ROULETTE is considered one of our most popular yachts according to our guests
From: 07/09/2019
To: 14/09/2019

Vacation in Greece with a sailing yacht

What is vacation for you? Are you a history maniac? Or maybe a traveler of the world? If you were asking me, vacation is the moment when I can pause time and relax. This would probably require some more ingredients in the background but I am quite convinced that my ‘dream vacation’ is on a sailing yacht. It is true I am not a mountain lover and I have always been a fan of the Greek islands but the calmness sea can provide is unique and amazing.

Look around you, see the world, meet the Greek islands. In a different way!

If you are in search of vacation that will make you feel more alive, if your imaginary place to be, is full of colors, sun, nature and sea. If you are triggered by emotions such as smelling the salty wind while the sunset dives into the sea, then sail a yacht with Yachtsailing.gr. We are your friend in Greece. Created by people with pure emotions and love for the sea for everyone that want to come and visit the Greek islands with style and safety onboard one of our sailing yachts or catamarans.

There is no doubt that yacht charter in Greece offers the ultimate freedom and independence. Here you will experience steady breeze and constant sun waving above you, while sailing. These are the top conditions for relaxed and predictable sailing vacation. Greece offers thousands of locations with unrivalled beauty to choose from. There are almost 2500 islands from which only 500 are inhabited. With a large number of Greek islands there are different locations with unique characteristics.

There is a top destination for everyone. Whether you seek for calm seas and green waters or you are a more adventurous spirit, Greece is here to dominate all your senses. The turquoise waters of the Ionian, the calm sea of the Saronic and Argolic gulf, the spicy atmosphere of the Aegean with the wild scenery as a background, or the celebration of nature in the Sporades area. These are few of the countless possibilities yacht charter in Greece has to offer.

A holiday in Greece consists of combined images with idyllic views, sandy beaches, spicy-looking ruins and of course turquoise waters of the surrounding sea.

Vacation in Greece gives you the total freedom to choose between beautiful landscapes of the mainland if you are looking to visit Greece in the winter, but most of all the ability to visit the famous Greek islands and enjoy the friendliness of the Greek people.

Greece is a popular tourist destination, would dare to say the most popular in the Med. It is perfect for families with children that want to relax, swim and enjoy the friendliness of the Greek people. In Greece you will find sandy beaches, clear and blue waters while the diversity of the landscape is present to all of the islands. Sailing vacation in Greece is perfect for combining relaxing and activities (if you like to) at the same time. Our skippers will be happy to show you in detail what sailing is all about and how you could use the power of nature to move from one island to another. See our skippered section for details in our weekly skippered sailing cruises. Personally I believe that sailing is a great asset for children since they get to know physics in practice. In addition, coming closer to nature, has always been helpful for everyone and inspiring as well. Most of the children will always have something to stay occupied with during sailing but most of all they will learn how to sail and navigate a sailing yacht. I would suggest to parents to select some of the extras that can be ordered onboard such as stand up paddles or inflatable canoes so when the yacht is moored you will have interesting toys for our younger friends but for those of you who are active you would surely workout well!

We have weekly sailing packages to fit all pockets (skippered or bareboat)and we strongly suggest you to examine all of your options if you consider visiting Greece for your holiday. We have made a detailed comparison to prove that sailing vacation in Greece is by far more affordable than renting a typical hotel, not considering the huge difference in what you actually get for your money if you choose to go on a sailing cruise. Check the detailed comparison here.

Either experienced or beginner, active or lazy we have the trip that will be fit to your profile. Our sailing yachts and catamarans are fully equipped and carefully maintained so your vacation in Greece will be a memory of a lifetime. The proof of our quality has the stamp of the Lloyds registry! Our yachts are carefully inspected yearly and certified by the Lloyds registry in Greece. Not to mention that we have an in-house technical department that has the ability to examine and certify everything in detail between our sailing cruises.

When it all comes down on the question where to sail most of you may be familiar with Mykonos and Santorini. It is true that these beauties are two of the most famous islands in the world. Mykonos is called the ‘island of the winds’. While Mykonos maybe one of the most beautiful islands in the world for your vacation and Santorini will make your holiday an experience of a lifetime, there are numerous Greek islands of equal beauty and sometimes more unspoiled that will make your heart beat. The lesser known islands are equally beautiful and at the same time more unspoiled and potentially interesting. The so called central Cyclades consist of Paros, Naxos, Antiparos and the complex of Koufonisia (Pano and Kato Koufonisi). If you are looking for absolute jewels of beaches with golden sand and at the same time crystal waters with a mix of green and blue color surrounding inhabited coves and sharp cliffs you have come to THE place. You will be amazed with the number of locations that you should be visiting while exploring these islands. To my opinion the best vacation in order to combine visiting all the hotspots but at the same time also to navigate into these amazing bays is with a sailing cruise in Greece. There are unlimited options if you choose to spend your holidays in Greece onboard one of our sailing yachts or catamarans.

However please pay attention to the following: We have many guests arriving in Athens and are determined to go to Mykonos no matter what. I always advise that the best vacation is a combination of weather and location. The most beautiful place that you see in a picture if it is combined with a strong wind will not give you the result you have in mind. There are equally beautiful and interesting islands to visit during your sailing holiday in Greece that will add up to the best vacation of a lifetime. Listen to our advise..

An additional reason why you should be choosing Athens for your departure is the above. In Athens you always have the choice to either visit the Cyclades as planned or to visit the Saronic and Argolic gulf if by accident the wind is really strong. Saronic gulf will give you the freedom of calm seas and lower sea waves (due to the land that stops the sea to create big waves) plus the beauty of hundreds of isolates coves to drop an anchor and relax.

We would suggest you to take our advice under consideration and rely on our experience to deliver the vacation of a lifetime. We have been offering sailing tours for your sailing holidays in Greece for almost 2 decades now and we will continue to do so. Your vacation moments are our fragile project and we will handle with care, efficiency and happy faces.

Visit Greece with the Yachtsailing.GR team and meet the Greek islands with our unique sailing approach! We hope to see you onboard soon!