Dream vacation in Greece with a Catamaran
Your Yacht
Your Captain
Your Chef
Explore Greece aboard your own luxury catamaran with a dedicated Captain and Chef. Since 1999, Yachtsailing.com has been crafting unforgettable sailing experiences across the Greek islands — combining comfort, privacy, and local expertise for a truly seamless journey at sea.
Explore our curated yacht offers
Browse our collection of luxury catamarans available this season.
Best seller
King of Diamonds, 56 ft
Our latest jewel fully refitted in 2024! 'King of Diamonds' comes with five cabins exclusively for the guests, and it is equipped with all the amenities of a 5 Stars floating hotel!
Up
to 10 guests
Refit 2025
Yacht price only
€14,000 /week
Casino Royale, 50 ft
Refitted in 2022! Sail with all the amenities of a 5 Star floating hotel! 5 cabins for up to 10 guests
Up
to 10 guests
Refit 2024
Yacht price only
€12,560 /week
Royal Flush, 52 ft
Among our jewels fully refitted in 2023! 'Royal Flush' comes with six cabins exclusively for the guests, and it is equipped with all the amenities of a 5 Stars floating hotel!
Up
to 12 guests
Refit 2024
Yacht price only
€10,000 /week
Poker Face, 45 ft
'Poker Face' is one of our best sellers. Equipped with Air Conditioning, and many additional
Up
to 8 guests
Refit 2023
Yacht price only
€8,300 /week
Best seller
Ace of Hearts, 52 ft
'Ace of Hearts' blends comfort and space, offering a seamless journey to Greece’s most stunning islands, fully refitted in 2024!
Up
to 12 guests
Refit 2025
Yacht price only
€10,000 /week
Your Summer 2026 in the Greek Islands
An authentic and genuine experience of the Greek Lifestyle. History, culture, and flavors this beautiful country has to offer. Taken to breath taking views, taverns, bars, and beautiful beaches. As well as Incredible landmarks and monuments which echo back into the ages.
See what our guests have to say
Real stories from our guests, sharing their unique journeys and unforgettable moments while exploring Greece’s beauty with YachtSailing
We were dealt a Royale Flush on the Casino Royale catamaran in the Greek islands. Yachtsailing.com 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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SuzyK from USA chartered Casino Royale to the Cyclades
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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j4metoo chartered Casino Royale to the Saronic
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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lizziebill chartered VEGAS to the Cyclades
I went on a week long sailing trip through yachtsailig.gr and it was absolutely amazing! There were 9 of us on the boat and it was perfect. The captain did a great job and got us to all of the sights we wanted to see, and had great food recommendations at every stop. The crew on board was so worth it! Coordinating the shopping and cooking for all of us would have really taken away from the experience, so having take care of it just made the trip so relaxing. I would definitely book with them again.
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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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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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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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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Top 10 Questions asked
All our trips are fully customizable. There is no fixed itinerary. The final route is shaped together with you, based on your preferences (how many hours you wish to sail per day, whether you prefer sightseeing or relaxation, interest in hiking, swimming, local cuisine, etc.) and—most importantly—the weather conditions at the time of your trip.
We do not pre-impose routes, nor do we force sailing long distances if conditions are unpleasant. The captain adjusts the plan daily to ensure the experience remains relaxed, safe, and enjoyable. You may also change plans during the trip and stay longer at places you enjoy.
The Cyclades and the Saronic Islands offer different sailing experiences.
The Cyclades involve longer distances between islands and have a higher chance of stronger winds, especially in summer. This makes them more adventurous and sometimes choppier. The Saronic Islands, on the other hand, have shorter crossings, calmer waters, and a more relaxed overall pace.
Neither option is “better” universally. The choice depends on your comfort with sailing conditions, how much time you want to spend under sail, and the overall vibe you seek. Weather always has the final say, and flexibility is key to a successful trip.
Ultimately, our goal is to ensure that you have the best possible experience during your time in Greece
Some islands can be combined within a week; others cannot—at least not without sacrificing comfort.
Mykonos and Paros are feasible from Athens within a week under favorable conditions. Santorini, Patmos, Anafi, and other southern or eastern islands are located over 150 nautical miles away and are not realistically reachable within a one-week sailing vacation without excessive daily sailing hours.
For these distant islands, we strongly recommend visiting them by ferry or plane before or after your sailing trip. The true experience of a sailing vacation lies in balance, not in covering maximum miles.
Trips are weather-dependent, but this does not mean they are canceled.
If strong winds or unfavorable conditions arise, the itinerary is adjusted to more protected areas. To date, we have not lost a single trip due to weather. Greece offers many alternative routes that remain beautiful and enjoyable even when conditions in one region are not ideal.
Flexibility is essential and a key for a succesful trip along with an elevated experience
The difference is considerably greater than simply having one additional crew member onboard.
Our captain-only option is available on selected smaller boats, primarily for experienced or more independent guests who may have sailed this way before, or for those who prefer a simpler option for budget reasons. It provides the boat and a professional captain, but it should not be considered the full Yachtsailing crewed experience presented throughout our website.
With a captain-only charter, the captain’s responsibility is first and foremost the safe navigation, operation and management of the boat. The captain plans passages, monitors weather conditions, sails and manoeuvres the boat, anchors and moors, and remains responsible for the safety of the boat and everyone onboard.
Everything related to the guests' day-to-day living onboard remains largely their own responsibility.
Guests should expect to shop for their own groceries and provisions, prepare and cook their own meals, serve and clear meals, wash dishes, keep the galley and shared areas clean and tidy, manage rubbish and generally look after the boat during the charter. This can also include purchasing everyday supplies or cleaning products if additional items are required during the trip.
There are also practical limitations to what one captain can provide. The captain cannot safely operate the boat and provide guest service at the same time. Depending on the weather, anchorage and circumstances, the captain may need to remain onboard and may not always be able to launch or operate the dinghy, provide repeated shore transfers, accompany guests to beaches or swimming areas, assist with water activities, carry luggage or leave the boat unattended.
In stronger winds or exposed anchorages, these limitations become even more important, as the captain may need to remain continuously focused on the boat, its position and the anchor.
With two crew members, the experience is very different.
While the captain concentrates on navigation, safety and the operation of the boat, the second crew member takes care of many of the practical aspects of everyday life onboard.
Depending on the crew arrangement, this includes meal preparation, provisioning assistance, galley duties, cleaning and maintaining the interior and common areas, helping guests throughout the day, assisting with shore transfers and water activities, and generally keeping the boat organised and comfortable.
Having a second crew member also allows responsibilities to be shared during anchoring, mooring, arrivals and departures and gives the captain considerably greater flexibility to operate the dinghy and assist with the itinerary without compromising the safety of the main boat.
For this reason, a minimum of two crew members is standard on our larger boats and is the arrangement we strongly recommend for guests looking for the complete Yachtsailing experience.
Captain-only can be a perfectly suitable choice for guests who understand this style of charter, enjoy being independent and are comfortable cooking, shopping, cleaning and looking after themselves onboard. It also allows us to maintain a more budget-conscious option on some of our smaller boats.
However, for guests looking for a holiday where the everyday responsibilities are largely taken care of and where greater assistance, service and flexibility are available throughout the trip, a two-person crew is unquestionably the option we recommend.
In order to plan an accurate budget you should consider the following costs apart from the boat price:
- Fuel: The fuel cost for the week will depend on the weather conditions, cruising distance and boat selection. Expect to use between 400 and 900 liters, with a cost of approximately €400 to €1600 for the entire week. You’ll take the yacht with a full tank and refill it upon return.
- End Cleaning fee: €300, covering the preparation of the yacht, including cleaning, one set of bed linens, towels, tea towels, dinghy, outboard engine, and gas bottles.
- Port docking fees: Port fees are generally minimal, ranging from €20 to €50 per night depending on the marina.
- Daily provisioning for the crew: Around €25-€30 per person, per day, for the crew’s meals.
- Guest provisioning: Depends on your preferences - food, beverages and/or alcohol you would like on board. Your cook will handle the shopping according to your preferences, ensuring everything is ready for your arrival.
Costs listed on the website are for the whole group (and not per person). Adding an additional passenger after your booking (providing the layout allows that) does not affect the weekly boat cost.
There is no fixed number of islands. The number depends on your preferences, the weather, and the pace you wish to maintain.
Some guests prefer changing location almost every day, while others enjoy staying longer in fewer places. Most commonly, guests visit 5–6 islands in one week, but this can be more or less depending on sailing distances and how much time you want to spend swimming, relaxing, or exploring ashore.
The itinerary remains flexible throughout the trip, allowing you to slow down or move on as you wish.
You are involved in the decision-making throughout the trip.
The initial route is discussed with the captain upon embarkation, taking into account the weather forecast and your preferences. From there, daily adjustments are very common. If you enjoy a specific island or bay, you may stay longer. If conditions change, the captain may suggest an alternative that offers a better experience.
Nothing is locked in advance, and spontaneity is part of the sailing experience.
Yes, provided the itinerary is planned thoughtfully.
For guests who prefer calmer waters or are sensitive to choppy seas, routes with shorter distances and more protected waters are recommended. The Saronic Gulf, for example, generally offers a smoother experience than the Cyclades.
Weather is always monitored closely, and itineraries are adapted to avoid unpleasant conditions. The objective is comfort and enjoyment, not endurance sailing.
Our charters operate on a Saturday-to-Saturday basis.
On embarkation Saturday, yachts are typically ready from around 14:00 at our base in Alimos Marina, Athens. You are welcome to arrive at that time, board the yacht, and settle into your cabins. If you have ordered provisioning in advance, everything will already be onboard.
Once on board:
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The captain will welcome you and introduce the yacht
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A full safety briefing will take place
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You will discuss your preferences and possible routes based on the weather forecast
After these formalities, the trip begins immediately. Depending on your plan and weather conditions, you will usually sail for a few hours and enjoy your first swim or anchorage the very same day.
On disembarkation, the yacht returns to the marina on Friday evening. You overnight onboard, and disembarkation takes place by 09:00 on Saturday morning. This timing allows the crew to properly clean, service, and prepare the yacht for the next guests according to our standards.
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