Island hopping on a boat under sail is probably the smartest way you can choose to explore the raw beauty of the Greek islands! Each day you wake up in a different place; there is no fixed itinerary, it's 100% your trip!

Windfinders sailing cruises

We run both private and individual skippered sailing cruises in the Cyclades archipelago.

The Yacht

The Skipper

The Cyclades

Cruises 2025

What's new in 2025?

We are excited to announce you that from May to October 2025, we will once more be operating both private and shared skippered sailing cruises from our base on the beautiful island of Paros, which is located in the heart of the Cyclades archipelago.

What is your style? Private cruise... or by the cabin?

When joining a Windfinders cruise you have 2 options: You can hire the entire yacht for yourself or you can decide to join a cabin charter where you will rent only one cabin on a shared cruise with other travellers. Cabin charters are a really nice way for solo travellers, couples or small groups willing to meet new travellers and share a week’s sailing together. A cabin charter is confirmed when a certain number of participants is reached.

How much does it cost and what is included in the price?

A week’s sailing on board Cinderella in high season amounts to about 1200 euros per person for a private booking. Booking a cabin only in a shared cruise costs 2600 euros for 2 persons sharing the same cabin or 2200 euros for a single occupancy of the cabin. Further information is available on the Booking page.

What is always included when booking with Windfinders

Accomodation on board Windfinder's beautiful sailing yacht "CINDERELLA"

Just a little over 50ft in length, Cinderella can accommodate up to 6 guests in 3 double cabins with attending bathroom.

The service of a professional skipper

Istvan is both the skipper and the owner of the sailing yacht Cinderella; he will be your skipper, interlocutor and also your guide throughout your sailing cruise.

Fuel is included

Fuel consumption of the main engine and the engine of the dinghy are included. This is for a reasonable utilisation of 2 – 3 hours per day.

No security deposit

Most charter companies require the charterers to leave a security deposit even in the event of a skippered charter. At Windfinders’ the skipper takes full responsibility of the yacht and its equipment.

benefits of sailing with us

Starting in the heart of the Cyclades archipelago

The island of Paros is the second largest island of the Cyclades Archipelago. Exactly in the center of the Cyclades archipelago, Paros is the ideal starting point for your holiday! It is easily accessible

Kitesurfing, Windsurfing and Wingfoiling are allowed from the boat

At Windfinders we are Kitesurfer, Windsurfer and Wingfoiler friendly! So you are welcome to bring your equipment on board and we will take you to those hidden secret spots which are only accessible by boat.

Important note: Windfinders does not provide any equipment, you have to bring your own. You have to be an independent to advanced rider able to ride upwind and familiar with all the safety procedures involved! Riding from the boat is at your own risk.

From June to September, the Cyclades are home to the sailing summer wind Meltemi, which turns the archipelago into Mediterranean's #1 sailing playground!

Check out our shared cruises for 2025...

May to October

Paros, Ios, Amorgos
and the small Cyclades

7 days and 6 nights

March to May

One way Athens to Santorini
via Milos and Folegandros

10 days, 10 nights

May to October

Kitesurfing cruise in
the home of the Meltemi,
the Cyclades

Private booking
upon request

What people say...

Windfinders Sailing Cruises Cyclades

4.9

Based on 41 reviews

review us on

Catherine Bouchard

20:45 18 Nov 24

Exceptional week last October where all the elements were aligned for our greatest happiness; ideal temperature, professionalism from Istvan, little attention from Sana. All this against a blue background of the Aegean Sea. We were only 3 passengers and it was perfect!

Bill Wolpert

13:33 23 Oct 24

If sailing is what you love, then spending time on Cinderella makes for some quality time. The boat is well equipped and comfortable at sea. Captain Istvan is very experienced and knowledgeable of the Aegean and Cyclades Islands, especially for lesser known destinations. 1st mate, Sanna, greeted us each morning with coffee and and a smile and took good care of us. Our week was everything we had hoped for...a dream vacation.

Fellay-Nguyen Thilan

15:58 21 Sep 24

A week with family and friends (5 adults) at the end of August. The boat is spacious, very clean, well equipped with all the details to relax. Istvan is professional, calm, allows you to participate in maneuvers if you wish, flexible, enthusiastic, full of humor. He will share his love of the Cyclades with you. Total disconnection guaranteed. THANKS !

Camille

12:30 16 Sep 24

We had planned a week on a sailboat with our two-year-old children, after being reassured by the skipper about the feasibility of the project. The sailboat is not suitable for small children. We had to stop the cruise after a day of sailing.Otherwise, for teenagers/adults, the boat is very beautiful, and the proposed itinerary looked very good.

Cezar Neagu

19:00 28 Aug 24

For the past four years, I've had the privilege of knowing a truly remarkable skipper in Greece, whose stories and experience have turned every trip into an unforgettable adventure. He showed us hidden gems only a seasoned sailor would know and he's always made sure we experience the best of what these islands have to offer. Here’s to many more years of finding the best secret spots and you graciously pretending we’re getting better at this sailing thing!Cheers, Istvan!!Your one and only,Cezar

Paloma Aparicio

12:59 13 Aug 24

Amazing experience sailing with Istvan. I think what I liked the most out of the week we spent sailing across the Cyclades was Istvan’s passion for the sea as well as his knowledge on the different islands we visited. We were a group of 6 girls with different needs and Istvan was able to make a taylor-made route for us catering for all of our needs. I would highly recommend this experience with Istvan as it was fun and adventurous as well as chilled and relaxed which was exactly what we were looking for. We did different cool things like fishing and cooking together to setting ground on a secluded island and watching the shooting stars at night. Istvan even let us help him out on the boat which was super cool and got some of us interested in learning more things on sailing ⛵️!

Hans Schendstok

12:25 04 Aug 24

Windfinders with our skipper Istvan made our dream come true. We had a fantastic sailing experience with our family. Beautiful islands and secret bays he knows everything. Proper sailing on the Cinderella with nice crossings to the other islands.We will definitely come back.Family Schendstok

Keegan Dum

16:47 29 Jun 24

We spent 6 days with Istvan and Sanna with our family (me, wife, and three kids from 7 to 14 years old) and this trip was a dream come true. Istvan listened to our desires and curated a trip that far surpassed our expectations. We stopped in amazing places only available to those that are sailing, with crystal clear azure water and remote beaches, cliff jumping, and amazing little villages. We enjoyed nights in quaint port towns but also nights with only the stars above us. We were worried we might get seasick but never did, with Istvan carefully plotting the course and navigating any high winds or choppy waters. We will absolutely be coming back and sailing again with Windfinders, and it’s hard to put into words just how wonderful this experience was for our family. Thank you Istvan and Sanna!

meagan kelly

12:44 22 Jul 23

I was unsure when our friends suggested we try a new way of sailing this year. But boy was i proved wrong. From the very moment we set foot on Istvan's boat Cinderlla, we knew we were in for an extraordinary adventure. With a beaming smile and an infectious enthusiasm, Istvan welcomed us aboard and instantly made us feel at home. His boat was not just a vessel; it was a floating wonderland of memories waiting to be created.Istvan's knack for curating mind-blowing and magical experiences day and night was nothing short of enchanting. Whether it was chasing sunsets over the horizon, witnessing the stars dance in the night sky, or adventuring to find bioluminescent, Istvan made sure each moment was infused with wonder and joy.What impressed us most was Istvan's ability to strike a perfect balance between being our charismatic guide and giving us the freedom to revel in the company of our friends.Sailing from island to island, Istvan offered us a unique proposition. He encouraged us to be as involved as we wanted in the sailing element. For the adventurous in our groip of four, there was ample opportunity to learn the ropes and feel the thrill of navigating the Aegean waves whilst those wanting to take a back peddle and enjoy the ride could do just that!The pinnacle of our voyage had to be the beach BBQ that unfolded on the untouched shores of Kero's. This uninhabited island became our private sanctuary for the afternoon leading into night, and Istvan's culinary prowess shone brightly as he cooked up a feast right on the shore line. Grilled delicacies, heavenly aromas, the sun setting anf the sound of goats echoing against the cliffs made it an experience straight out of a fairy tale.Having sailed Greece a few times before, we can confidently say that entrusting our journey to Istvan and Sanna was a game-changer. Unlike a third-party company, Istvan brought a personal touch, a genuine love for sailing, and a flair for entertaining that elevated the entire voyage. His passion for the sea was infectious.The decision to sail with Istavan was a no-brainer.To all sea-loving souls out there, we wholeheartedly recommend this dynamic duo for an unparalleled journey that will leave you yearning for more. Trust us; you won't be disappointed!

Bec

08:23 20 Jul 23

We had an incredible week onboard Cinderella. Istvan is very passionate and loves sailing, exactly what we wanted for our week in the Cyclades. From secluded bays to secret caves, Istvan knew all the spots to blow our socks off.The boat—owned by Istvan—is beautiful and well maintained. You can immediately tell the difference with a chartered yacht.Istvan is also passionate about photography and took some great shots for us during the week.Our best sailing experience to date and we will definitely be back!

More reviews

A fantastic week sailing the small Cyclades

Our family of 6 spent a week on board the Cinderella from 1-8 August as part of a longer multi island trip in the Cyclades. The week exploring the small Cyclades, hidden coves and quiet beaches, as well as decent sailing hours, with skipper Istvan turned out to be the highlight of our summer vacation. As we were advised by someone, the skipper and his/her knowledge of the area and the ability to get along with the guests can make or break the trip. With Istvan we hit bingo as he turned out a fantastic host for us and the kids, always willing to embark on an activity, on sea or on land. He knows his ship and the Aegean sea and that gives a very comfortable and safe feeling. Equally important, Istvan is really a nice guy, very relaxed about almost everything. Many thanks Istvan for a great week on board the Cinderella. 5/5 stars for sure.

– Hoes family from Netherlands

Go for Istvan

We went on our first sailing trip ever five years ago and decided to choose Istvan Ferrare as a skipper. It was said that he is one of the most trustful skippers in the agean sea. After one week of sailing with him we got very good friends, got the sense of sailing and we NEVER felt unsafe!! Istvan has a great sense of humour and he is really sensitiv,he is an entertainer and skipper in one person . He would never risk something without thinking or do something unsafe. Istvan is an expert in finding the best places for you in the Agean. We really enjoyed every sailing week with him.

– Spreizer family from Austria

Just had the most amazing sailing…

Just had the most amazing sailing holiday with Istvan and his boat Cinderella. We felt completely safe and secure on the boat, Istvan’s knowledge and experience is incredible and he took us to fabulous beauty spots that are not on the commercial path. We would recommend Windfinders to everyone with confidence…..Istvan is not intrusive and gives you space and privacy so if you are thinking of booking a sailing holiday then book Windfinders. Thanks Istvan

Susan from UK

Perfection on the ocean waves ......

Just back from a week of sailing on Cinderella with Istvan.
Cinderella is beautiful with everything you need and plenty of space. Istvan is just perfect! He knows the best places and is extremely competent which makes you feel totally safe. Istvan is very knowledgeable and an excellent host.
I will definitely book again and will be recommending without any hesitation whatsoever.

Josephine from UK