Sailing holidays in the Cyclades with a local skipper
Discover the treasures of the Aegean Sea - a collection of islands
with their own unique charm, landscapes, and coastlines. The
Cycladic Islands act as a brilliant destination to unwind, relax,
and connect with some of the most stunning natural beauty. Explore
the stunning Santorini, Mykonos, and Ios with a passionate, local
skipper.
BEST PRICE GUARANTEE
If you find the same experience for a lower price elsewhere, we’ll match the price.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Sailing holidays in the Cyclades with a local skipper
Cette croisière avec Nikos et Mathilde était notre première croisière en voilier, et nous avons adoré! L'itinéraire a dû être revu du fait des conditions climatiques et nous avons finalement navigué dans les îles Saroniques, mais l'expérience est restée exceptionnelle. Quelle sensation que celle de se laisser porter au gré du vent. Nikos nous a initiés à la navigation et aux manœuvres, et grâce à la planche de paddle et à l'équipement de snorkeling, nous avons profité à fond des plaisirs marins. Nikos et Mathilde nous ont tout de suite mis à l'aise, sachant se montrer très souples et réactifs, désireux de satisfaire à la moindre de nos envies, sans jamais s'imposer. Les bons petits plats de Mathilde sont un vrai plus!!! La Grèce est un pays magnifique, et les Grecs un peuple charmant. Nous avons visité différents villages traditionnels et nous n'oublierons jamais l'effervescence de ce petit port d'Hydra, où tout le monde s'affairait à faire une petite place pour notre voilier... MERCI.
This was ou first time joining this type of holiday and I have to say that it went beyond expectations.
First of all the communication with Sandrine and Jean-Marc have been very prompt and clear from the beginning.
The boat is exactly (or better) as in the pictures and description provided, very comfortable.
Sandrine and Jean-Marc have been more than just skippers, they have treated us like friends and did their best to accommodate our wishes. I have had few episodes of sea sickness and they adjusted the trip to make sure I wouldn't suffer the sailing time for too long.
The islands they have chosen for the itinerary were not the usual touristic spots, they really took us to beautiful places like Pirates Bay in Milos, unforgettable.
They were very kind by preparing us breakfast and lunch or dinner in case we wanted to stay on the boat.
Also, we didn't lack of privacy at all and we have strongy appreciated that. I will definitely consider to joining them again for another holiday!
vacanza PERFETTA! La barca era spaziosa e dotata di ogni comfort e divertimento ( kayak, musica ecc). Vasilis e suo figlio Panos sono stati super gentili e disponibili con noi esaudendo qualunque nostro desiderio e preparandoci dei pranzi e delle cene meravigliosi!! ( spesso con pesce pescato da loro sul momento). Grazie Vasilis per aver reso questa vacanza INDIMENTICABILE!
Cpt Vasilis and his son Panos Made our trip a Great experience. The boat was very comfortable and equipped with a lot of amenities ( kayak, Music etc..). Vasilis has always been ready to fulfill our requests to have us enjoy the stay. He’s also a great cook , We had great meals with seafood ( fished by him during the very same trip ) and with other greek specialities.
Thanks so much Vasilis to have Made our vacation so memorable!
Un Abbraccio pour Riccardo, grâce à toi une formidable croisière dans les Cyclades, j'en suis émerveillé, du vent, une mer Égée toute belle avec Filippo aussi, tout bien la navigation, la table, la compagnie. A bientôt, j'espère.
J ai vécu 2 semaines extraordinaire a bord de Giada avec Riccardo , La 1ere semaine nous avons navigués de Mykonos jusqu a Santorin , pleins d escales dans des endroits fantastiques , que ce soit les criques ou ports . Je suis partie seule mais des le 1 er jour avec l Equipage je n ai eu aucuns problèmes . Merci encore Riccardo et BON VENT :)
Une semaine extraordinaire en voilier avec Christopher et Marie
Accueil sympa parcours extra baignade dans de superbes criques
Bonne musique le soir et repas délicieux
Que du bon temps
Adam et Allan pris leur premier cours de navigation avec le captain Christopher
N’hésitez pas à embarquer
Merci mille fois
Adam Allan Zena et Patrick
Nous venons de voyager une semaine avec le Capitaine Vardis sur son bateau : Atlantis 43, à travers les îles des Cyclades. Ce fut l'une des plus belles expériences, aussi bien maritime que la rencontre avec ce superbe skipper. Nous avons partagé de nombreux moments de joie, de rire, de plaisir, à naviguer sous le soleil de la mer Égée. Il nous a fait découvrir la Grèce comme jamais, ainsi que ses très bon repas. Enthousiaste, professionnel, fin connaisseur de la mer, des criques où nager dans cette mer d'un bleu typique, nous pouvons que vous le recommander fortement ! Merci encore Capitaine et à bientôt, je l'espère !
What a sailors! Vasilis and his son Panos have been amazing in hosting us and guiding us across the Cyclades. They are real sea dog who has sailed the seas for decades. We have been navigating in full security and comfort across 3000 nautical miles even if sometimes wind and current were against us. Vasilis and Panos have always been attentive to our needs and willing to discuss any itinerary decision. They took us to unique islands snorkeling and spearfishing spots, beautiful beaches with natural hot springs, idyllic white villages. All of their three vessels fleet are fully equipped and comfortable for long cruises, including rigid sun protection structure, SUPs, kayaks, fins and masks, spearguns. Furthermore he is great chef: don't miss his Kakavia fish soup! I had such a great sea-life experience that I can only give my best recommendation to this Ikarian crew. I would jump on board of their boats tomorrow!
Vacanza indimenticabile con uno skipper di rara esperienza e simpatia! Massimo ci ha fatto veleggiare tra alcune isole di una bellezza mozzafiato: una vacanza che ha unito la possibilità di vedere calette stupende con ad una buona dose di divertimento, risate e buon cibo.
Consiglio Massimo come skipper specialmente per chi la barca a vela la vuole vivere a 360° coniugando la voglia di vacanza a quella di "imparare" a vivere il mare da un'altra prospettiva. La passione di Massimo per la barca a vela e il mare è stata trasmessa a tutto l'equipaggio fin dalla prima traversata.
Mi sento di consigliare Massimo al 200% e sicuramente torneremo a bordo della sua fantastica barca per nuove avventure e traversate insieme.
Buon vento caro Skipper e grazie mille per la bellissima esperienza!
Una bellissima settimana in barca
Itinerario bellissimo e preparato al meglio
Pierluigi è stato un capitano indiscutibile ma anche pronto a divertirsi insieme a noi
Con Nicoletta hanno reso la settimana piacevolissima... solo un difetto: è passata troppo in fretta.
Watching Luigi was watching a master at work. He n is an expert sailor and also as a gernerous caretaker of the guests. He goes beyond to ensure that everyone feels welcome, is enjoying the experience and works tirelessly without letting it show to build camaraderie and good will.
I will always remember the crystal clear waters the rhythm of the waves, the laughter of the new friends. A true gift to be on the Grail.
Phil è una persona disponibile e di gran compagnia con la battuta sempre pronta, siamo stati molto bene!
Questo tipo di viaggio è un’ottima soluzione per raggiungere le varie isole in tutto relax senza dover prendere traghetti e stressarsi con i bagagli. In più si impara qualcosa sulla vela e si possono incontrare dei simpatici compagni di viaggio. Noi siamo stati fortunati! :)
George is an excellent skipper, competent and professional. He is forthcoming, humorous and relaxed. George was always ready to help and made sure you feel comfortable. The boat was well kept and modern. The crew had lots of possibilities to participate as they wanted. We had a fantastic sailing week exploring the Greek islands with George's local expertise.
La nostra vacanza con Greg e Aga è stata fantastica! Ci hanno accolto con gentilezza e simpatia a bordo. Hanno sempre fatto il possibile per accontentare le nostre richieste e ci siamo molto divertiti con loro. Per me e i miei due figli è stato importante!
La barca è grande, comoda e c'è spazio per tutti.
L'intinerario è perfetto per conoscere le Cicladi e visitare le isole più belle. Greg e Aga ci hanno lasciato tempo a disposizione per esplorare a terra e poi rilassarci durante gli spostamenti. Torneremo!
Our holiday with Greg and Aga was fantastic!They welcomed us with kindness and sympathy on board. They always did their best to satisfy our requests and we had a lot of fun with them. For me and my two children this was very important. The boat is large, comfortable and there's a lot of room for everyone. The itinerary is perfect to get to know the Cyclades and visit the islands. Greg and Aga left us time to explore on land and then relax while travelling. We'll come back!
Si può solo che parlar bene di Claudio!
È una persona meravigliosa, velista di indubbia passione e capacità! Mi sono affezionata a lui e ai miei compagni di viaggio nel percorrere insieme questa settimana divertente e piena di vento e di onde ed è iniziata anche una bella amicizia oltre che concretizzata la passione per la vela!
Posso solo dare il voto più alto a Carlo e a questa vacanza. Avevo promesso 8 stelline ma il punteggio massimo possibile è di 5. Sappiate però che le 8 stelle sono più che meritate! Nonostante fosse la mia seconda esperienza mi sento assolutamente di dire che con Carlo ho vissuto la mia prima vera vacanza in barca a vela. Lui preparatissimo e professionale, sempre calmo e paziente con tutti; aveva organizzato tutto già prima di partire e non ha lasciato nulla al caso. Ci ha portato in baie meravigliose con colori stupendi e tramonti indimenticabili. Rade fantastiche, in alcune eravamo totalmente immersi nella natura illuminati da luna e stelle; in altre eravamo nelle vicinanze di paesini caratteristici che avevano il loro fascino. Non è mancata la fortuna di vedere delfini e tartarughe!! Equipaggio TOP con tante risate e nuove amicizie! Una mix di mare, cultura, divertimento e relax!
Consiglio a tutti un viaggio con Carlo!
It was an amazing trip.
Max is an excellent skipper, very Nice and take care with the crew.
I really recommande à sail trip with him.
Thank you for everything
See you
Prima esperienza in barca a vela...che dire fantastica, emozionante incredibile!!! Nn potevo trovare skipper migliore! Competente, preparato, simpatico, discreto sempre pronto a far interagire il gruppo con le manovre! Insomma se volete provare una vacanza alternativa in piena sicurezza che dire Daniele è una garanzia!!
Io nn posso dire che alla prossima!!
Una splendida vacanza in buona compagnia tra le isole cicladi, sempre accompagnati da un sostenuto Meltemi, ma tranquilli per il sicuro e pronto governo dell'imbarcazione da parte di Daniele e della sua compagna Ellina. Grazie, a presto! :)
Christian è stato simpaticissimo...l’assistente sempre gentile e disponibile! Spazi ampi nelle cabine del catamarano, vacanza comoda, nonostante il mare mosso in Grecia!!! Il gruppo molto piacevole!
È stato divertente tutto, insomma!
Ve lo consiglio!!!
la vacanza si è rivelata superiore alle nostre aspettative sia per quanto riguarda la parte naturalistica che l'organizzazione della vita a bordo. Il livello di attenzione ai bisogni del cliente e' stata molto alta. Accoglienza, Gentilezza e simpatia non sono mancati per non parlare della possibilità di imparare e far pratica di vela. Le visite alle isole sono state guidate così come le soste culinarie al fine di cogliere il meglio di ciò che il luogo offriva.
Luca... una bella persona che svolge con passione, generosità e competenza il suo lavoro.
Sas Efcharisto' poly kai tha sas do syntoma
Grazie molte e arrivederci a presto! ????
I had a fantastic week sailing around some of the most beautiful Cyclades islands on Phil's boat 37 Rocks!
A gorgeous & well kept sailboat with just one other sailmate. We all got on very well and had a fantastic time!
Phil is a very experienced, knowledgeable, reliable, and easy going skipper. He likes to keep things tidy and orderly which is great and to avoid any possible drama! So everything is always well prepared and makes our sailing experiences very relaxing!
All decisions as to where to sail and how to go about sailing is always discussed in advance and he is always available to answer any questions that we have. Phil also keeps on top of the ever changing weather patterns, so we didn't have any surprises. He was our great tour guide who also showed us around the various islands that we visited and took us to some very cool places. I would highly recommend him to anyone on Sailsaquare.
Nous avons eu la chance de passer une semaine au côté de Jérôme et Depy pour une première croisière dans les cyclades. Notre séjour à été merveilleux a tout point de vue, un bateau super, des paysages magnifiques, mais surtout un accueil inoubliable.
Jérôme et Depy ont pris le temps de nous faire découvrir leur univers, de nous expliquer les principes de la voile, de partager avec nous des plats authentiques, de nous emmener dans des coins intimes et splendides, également d'être à l'écoute de nos envies, etc.
A eux deux ils nous ont conquis et donné l'envie de recommencer très vite l'aventure !
Un immense merci !!!
"Bon Vent" :)
David & Sidonie
Conosco Andrea da diversi anni, lo reputo una persona molto piacevole ed uno skipper preparato ed attento. Abbiamo piu' volte navigato assieme, ed ogni volta che e' al timone posso essere sicuro che non farebbe nulla di differente da cio' che farei io.
8 reasons to choose the Cyclades for your next sailing holiday:
Home to some of the most spectacular beauty in the Greek Isles in Santorini, Mykonos, and Ios
Lesser-known treasures of the Cyclades such as Sifnos, Koufonisia, and Amorgos which are regarded by expert skippers as some of the most perfect Greek islands
An ideal climate for sailing from April through to October
Learn the special sirtaki dance in the area’s street festivals
Taste the popular Greek liquor, ouzo, with a meal of local produce
Discover some of the world’s most charming coves and lagoons
Immerse yourself in the regions iconic white, cubic architecture and charming fishing villages
The best places & specific destinations to visit during your sailing holidays in the Cyclades:
Sailing the world renowned landscapes of Mykonos
This island of Mykonos, a favourite holidaying spot, is recognised for the beauty of its hilly landscapes, sandy beaches, and picturesque Cycladic white country chapels. Where as, the crescent-shaped Santorini, or Thira, as it’s otherwise known, is in fact a group of islands in the southern Cyclades.
The volcanic complex of the Santorini Islands has crafted some of the most unique arrangements of rock and ocean - while sunset images from the famous Caldera have become synonymous with romance. Then there is the island of Ios, known as Nios by the locals, and considered by many as one of the most beautiful islands in the Cyclades. The Panayia Gremiótissa church that stands at the highest point of Ios offers a striking view over the town and out onto the open sea.
Exploring the secret beauty of the Cyclades
The best kept secrets of the Cyclades are the islands of Sifnos, Koufonisia, and Amorgos. Sifnos with its red bougainvillea that hugs the white of the buildings, as the gentle Meltemi breeze flows over the hills and onto coastline. Koufonisa is said to compete with the best of Greek islands on all fronts. The port of Koufonisa sits on the islands only village, here some of the most charming blue lagoons are being secluded. Amorgos rises dramatically from the Aegean, creating extremely unique landscapes, and is described by skippers as a charm that you most confront at least once in your life.
The Cyclades, which originates from the Greek word for ring or circle, is in fact made up of around 220 different islands. This variety in island, partnered with the Meltemi winds, make for some of the best conditions for a sailing holiday full of discovery and fun.
Tips to help you to better plan for your next sailing holidays in the Cyclades:
As the region boasts a warm climate for much of the year, sailing the Cyclades is recommended between early April and late October.
You can find experiences for a week in the Cyclades with a skipper from €500 per person. This figure excludes transport to and from the holiday. It is important to remember that depending on the month of travel and style of boat pricing is subject to change.
The two main airports in the area are based in Mykonos and Santorini. If not clear in the holiday listing, reach out to a holiday’s organising skipper to understand more precisely the most suitable transport options.
The best sailing holiday itineraries for your next adventure in the Cyclades with a skipper:
Due to the Cyclades having approximately 220 islands, there are a great number of different sailing holiday itinerary options. Popular itineraries include the exploration of some of the areas most popular islands including - Sifnos, Poliegos, Kimolos, Milos, Paros, Syros, Santorini, and Mykonos.
Such concentration of different islands means that some skippers like to propose visiting a new island each day. If there are shorter holiday time frames available, there are many itineraries that revolve more heavily on the Small (otherwise known as Little, Minor or Lesser) Cyclades.
