• Dream vacations in Greece
    with a sailing yacht

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  • Dream vacations in Greece
    with a sailing yacht

    Book Now
  • 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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Ranked as the No1 Boutique sailing company in Greece

Realtime Availability

Browse through excellent options among our private fleet. Departures take place on Saturdays and on weekly basis. Filter among different boats types among our certified private boat range

Boutique trip planning

A dedicated travel advisor at your disposal free of charge, experienced route suggestions away from tourist traps! Professional crew trained yearly. Ask for a free quotation from one of our experts

Hundreds of genuine reviews

Operating since 1999, we honor Greek hospitality. Certified member of the Greek ministry of Tourism. Awarded as the No1 boat rental company in TripAdvisor


We specialize in 3 sailing vacation categories

Bareboat Trips

Charter excellent boats from our extensive monohull or catamaran range. Top notch maintenance, certified by the Lloyds registry, trip suggestions and 24hr assistance

Skippered Trips

Award winning skippered services, experienced captains to take you to customized itineraries off the beaten path. A unique vacation experience even for the most demanding travelers

Fully custom crewed trips

No hidden fees or surprises. Just select the dates and let us worry for all the rest. Experienced crew, fully customized services endless moments of happy faces

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 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

The “Casino Royal” boat was pure magic. I listened to the wisdom of Yacht Sailing guru Eugene - who helped me plan a stunning week long adventure with Vicky & Captain Harris which gave our group the time to explore and rest in perfect measures. I have traveled the southern Greek islands extensively but never seen the northern ones and they were truly a delight. The wisdom and cheer Captain Harris shared with us, along with all his tips and tricks - truly took our escape to the next level. Additionally this company offers excellent support to his captain and passengers. When the sound system proved less than ideal - the minute we docked we got an upgrade and a whole new system. This is something that’s so important - in a world full of less than ideal charter companies. If you want a top-notch, warm hearted experience ... book the casino royal with this amazing crew. You won’t want to go home.

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Tripadvisor member - j4metoo

This is my first time on a catamaran. I didn’t know what to expect so everything was a new experience for me. From the time I arrived at the Alimos Marina and was greeted by Joanna and Eugene I felt very comfortable. In a short time we sat down with our Captain, George, who explained the salient points and answered all our questions. As we left the dock and went sailing, I knew this experience would be everything I hoped. Every morning sitting on the deck with my coffee was enchanting. New ports of call, meeting new folks in the town was a sweet experience. George suggested places to eat, shop, and noteworthy sites to check out. Probably the highlight of each day was our evening meal with Our Captain. He shared memorable sea stories, and his experiences on the seas kept us laughing and up late. We were sad pulling back into the marina as the trip came to a close. This was a trip of a lifetime for my husband and myself.

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Tripadvisor member - lizziebill

Boat chartered (Big Deal) Crew Theodore & Fedra and the companys name yachtsailig.gr I went on a week long sailing trip through yachtsailig.gr and it was absolutely amazing! There were 9 of us on the boat Big Deal and it was the perfect size. The captain Theodore did a great job and got us to all of the sights we wanted to see, and had great food recommendations at every stop. We also had Fedra on board to help with the cooking and she was so worth it! Coordinating the shopping and cooking for all of us would have really taken away from the experience, so having Fedra take care of it just made the trip so relaxing. I would definitely book with them again.

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Tripadvisor member - Hilary B

There are no words to completely describe what a wonderful week we had sailing the Cyclades on the Blackjack with our Skipper Joe!!! Everything went according to plan from the very first day, transfers from the hotels to the Marina and our provisions on the boat. I truly don't believe it would have been as fantastic though if our Skipper Joe wasn't with us. He listened to us and gave us suggestions as to what to see and experience and also became part of our crazy group!!! We ate and drank our way from island to island laughing all the way. Greece is a magical place. By day 3 we were already talking about when we would be back for a two week sail, and we won't be doing it without Skipper Joe!!

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Tripadvisor member - Ann N

Just spent a magical week cruising around the Cyclades with captain George Maleas and our group of three couples. Having never done a trip like this before, we had lots of questions that were patiently and thoroughly answered by Eugene via email in the months leading up to our departure. Joanna was also helpful and kind while helping us with transfers, boat provisioning, and payment. We couldn't be happier about our amazing experiences with yachtsailing. Everything far exceeded our expectations from the quality of the catamaran to the places we visited to our knowledgeable captain. George really knows these islands well and took us to some beautiful coves for swimming and quintessential little island villages for exploring. We visited Poros, Milos, Kimolos, Serifos, and Kythnos and each island was more beautiful than the last. Thank you, George, Eugene, and the entire yachtsailing team for an unforgettable experience! It was a trip of a lifetime!

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Tripadvisor member - amykW2873BD

I went on a trip with 3 other guests (2 couples) in late April/early May and we had an absolutely phenomenal time, and loved working with the Yacht Sailing Gr team. Upon first email, they were quick to respond and providing lots of clear information around every question we asked - Eugene made us feel like we were covered. Prior to arrival, they helped us with grocery shopping and stocking the boat. Finding the boat at the marina was easy (took 5 mins!), and they generously gave us an upgrade to the Poker Face because our other catamaran was having some engine issues. Poker Face is an astoundingly beautiful boat - everything was not only clean, but working in perfect order. So many wonderful places to lounge, read, play games or have a drink. Within an hour of getting situated, we were out on the water making our journey (groceries were already loaded in on the boat!) Eugene was there to greet us and helped us get situated, manage payment and work on route with our captain, which leads me to my next point... Our captain Theodore was incredible - he helped us plan a route that accommodated ALL of our needs/desires (less crazy/crowded, balance of Saronic islands and Cyclades), all while factoring in weather and experience on the journey. We had so much fun with him, and it wouldn't have been the same trip without him. All the same, he was also respectful of our space and gave us time to hang out independently as well. He was respectful, hilarious, accommodating, and always made us feel safe on the boat. Had lots of great restaurant, bar and hangout recommendations along the way that were phenomenal. Our journey was unforgettable and covered so many places we wanted to see in a short amount of time - Hydra, Kitnos, Paros, Siros and back, all in 6 days. I only wish we could have stayed longer! Our experience was so wonderful, I already have plans to return back to Greece and hopefully work with YachtSailing to explore other areas of the Cyclades for a longer period of time. The boat is your home base, your transportation and your entertainment - I loved life every day. I cannot thank the team enough for taking us out to seas, offering endless great recommendations and making our trip so special. We'll see you again soon!!

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Tripadvisor member - Sarah H

We are a family of five who travel often. Everyone agrees that this was one of our favorite trips ever. Our skipper George Maleas and hostess Josie were integral in making memories we will not soon forget. They both listened carefully to what we wanted and made suggestions accordingly. We ended up completely changing our itinerary based on their suggestions and were sooooo happy we did. We saw and experienced things the typical larger Greek Island Tourists are not privy to. Also noteworthy was the superb (REALLY superb) communication from the team (Eugene in particular). Rest assured this is a company who states all costs & information BEFORE booking. An honest company that can and should be trusted.

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Tripadvisor member - Amynorton2014

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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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!