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Sailing holidays in Greece with a local skipper

Sailing holidays in Greece with a local skipper

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

  • Sailing Holidays
  • Greece

COVID‑19

Book without stress paying a small deposit, cancellation is free!.

  • 14 reviews
    1 discounted
    spot

    Sailing on the discovery of the Dodecanese

    from 6 March - 7 nights
    Dodecanese Greece
    Join in on this experience!
    399 357€ Per person
  • 2 reviews
    5 discounted
    spots

    Athens to Mykonos - through Western Cyclades, Syros, Tinos. Semi private-only 5-7 guests

    from 8 March - 6 nights
    Cyclades Greece
    1 person interested
    in this holiday
    794 740€ Per person
  • 9 reviews

    10 days from Athens to Santorini via Milos and Folegandros

    from 9 March - 9 nights
    Cyclades Greece
    Join in on this experience!
    840€ Per person
  • 2 reviews
    5 discounted
    spots

    The BEST of the Cyclades. Only 5- 7 guests - travel in comfort and avoid the crowds!

    from 15 March - 6 nights
    Cyclades Greece
    Join in on this experience!
    794 740€ Per person
  • 9 reviews

    10 days from Santorini to Athens via Milos and Folegandros

    from 21 March - 9 nights
    Cyclades Greece
    Join in on this experience!
    840€ Per person
  • 2 reviews
    5 discounted
    spots

    The BEST of the Cyclades. Only 5- 7 guests - travel in comfort and avoid the crowds!

    from 22 March - 6 nights
    Cyclades Greece
    Join in on this experience!
    794 740€ Per person
  • 4 reviews
    6 discounted
    spots

    Combo itinerary - Saronic & Cyclades mix. Customised itinerary for private chartering the whole boat

    from 29 March - 6 nights
    Saronic Islands and Athens area Greece
    Join in on this experience!
    860 755€ Per person
  • 2 reviews
    5 discounted
    spots

    The BEST of the Cyclades . Only 5- 7 guests - travel in comfort and avoid the crowds!

    from 29 March - 6 nights
    Cyclades Greece
    Join in on this experience!
    794 740€ Per person
  • 31 reviews

    The most beautiful holiday is on a sailing boat, with Manuele and Camilla

    from 30 March - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    683€ Per person
  • 39 reviews

    Easter in Greece in the beautiful Argolic Islands between sailing, gastronomy and history

    from 1 April - 5 nights
    Saronic Islands and Athens area Greece
    Join in on this experience!
    420€ Per person
  • Sporades islands - Sailing holidays are more than just holidays

    from 3 April - 7 nights
    Sporades Greece
    Join in on this experience!
    662€ Per person
  • 1 review

    Discover the North Sporades with local Skipper!

    from 3 April - 7 nights
    Sporades Greece
    1 person interested
    in this holiday
    531€ Per person
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Reviews - Sailing holidays in Greece with a local skipper

1080 reviews
20 / 10
Luc B.

Luc B.

review about Unique Sailing Vacation September 2020

10 / 10
Excellent navigateur et marin connaissant parfaitement la région. De +, il parlait bien anglais. Bon bateau très propre et confortable malgré la petite taille de la cabine. Il nous a toujours proposé d'excellents petits restaurants et nous a aidé à visiter les îles de Skiathos et Skopelos Nous comptons retourner en Grèce et naviguer avec Lambros.
Aleksander D.

Aleksander D.

review about Where the Meltemi blows. The charm of Patmos, Leros, Lispi, Levita and Kalimnos. August 2020

10 / 10
Guido is an experienced skipper that leaves no room for surprises. He's fully proficient using sailing apps for navigation and weather forecast to plan routes and happy to share its knowledge with the crew. He's keeping the boat in immaculate condition for the crew to fully enjoy the time onboard and the sailing experience. I'm happy to have met Guido and the rest of the crew on this occasion and would be more than happy to book sailing with him again.
Susan J.

Susan J.

review about In the footsteps of Ulysses ... August 2020

10 / 10
Stephane, was warm, friendly and welcoming as soon as I stepped out of the taxi he had organised for me. The week was amazing, good food and company. For me the night in the bay “eating on board and star gazing” was wonderful. We saw the milky way. Swimming and snorkelling in secluded bays, crystal clear waters, what more can you ask for. Each evening we visited a different island, sailing into Kefalonia, berthing and sitting on deck with a sundowner was so memorable. If you want a sail around the Ionian Islands I couldn’t recommend Stephane highly enough, “your wish is his command”???? there was nothing he wouldn’t do to try to help anyone. Amid Covid-19 the boat thoroughly cleaned, galley hygiene was impeccable. Would I go back? ABSOLUTELY ??????
Jean-Baptiste V.

Jean-Baptiste V.

review about Sailing course in the Cyclades August 2020

10 / 10
Super semaine avec Sylvain Virements de bord, travail sur carte, manoeuvre de port, navigation de nuit Sylvain est très pédagogue. Avec un équipage de tous niveaux, il a su s'adapter aux attentes de chacun. Dans les différents mouillages, les eaux cristallines et les plages désertes permettent de pratiquer baignade, snorkeling et farniente entre deux nav'. Sylvain a une grande expérience de la mer et maîtrise parfaitement son sujet. Super expérience. À refaire. Nous recommandons !!!
Lydia M.

Lydia M.

review about 4 day sailing adventure! Max 6 guests in 8 berths.This year travel in comfort & avoid the crowds August 2020

10 / 10
Adrianna and Radu are the hardest working team on the islands and their goal is to figure out exactly what you want from your sailing vacation and provide it. They were sensitive to what we were looking for- local/ insider sights, some nightlife, the best spots for snorkeling and paddle-boarding, and have great recommendations about what to do and see at each port. Quad biking on Kythnos is a must! They were super informative and helpful from my first enquiries until the day we left. I and my travel buddy will be back for sure!
Claudia G.

Claudia G.

review about By boat between Kefalonia Ithaca and Zakynthos August 2020

10 / 10
Che dire? Gianfranco è un capitano eccezionale con grande esperienza , un vero lupo di mare, un ottimo skipper , un perfetto chef e da buon romagnolo persona gioviale e molto ospitale. La sua barca è assolutamente confortevole, spaziosa e ben tenuta......e poi c'è il mare cristallino che la fa da padrone. Buon vento!!!
Devon C.

Devon C.

review about Premium one way sailing trip - taste BOTH the Saronic AND Cyclades islands. From Paros to Athens August 2020

10 / 10
Where to begin... Spiros is without a doubt one of the most attentive, relaxed, talented people we have met- sailing aside. In regards to sailing, Spiros was an absolute wonder to have as a skipper. We had some days with a lot of wind (meltemi) and waves but he was both re-assuring, fun and made the experience exhilarating. We not only had a wonderful holiday visiting wonderful places but we also made a friend in him. We will be back. Devon et Hugues
Luca P.

Luca P.

review about Ulysses' course, August 2020

10 / 10
Skipper e catamarano Top, fornito di ogni ben di dio... Sup, canoa, attrezzatura da sub etc... Fabio oltre ad un'ottima preparazione è molto bravo a insegnare un po' di vela agli interessati, sembra strano, ma nei Charter é cosa rara. Consigliato a chi desidera passare una settimana di relax all'insegna di mare vela e tanta natura. Da non dimenticare il simpatico Jack, il cane marinaio buonissimo, sempre alla ricerca di essere coccolato da tutti, la mascotte della barca!
Francesco T.

Francesco T.

review about Are you a lover of nature and crystal clear seas? JOIN US !!! ZERO STRESS, INCLUDED HOSTESS July 2020

10 / 10
Vi consiglio vivamente di non esitare neanche un momento a prenotare una vacanza in barca vela con Andrea e Susanna! Saranno attenti a soddisfare la vostra voglia di relax ed avventura in mare sulla loro barca, tenuta in maniera eccellente. Ne hanno una cura impeccabile, è sempre pulita ed in ordine, e qualsiasi imprevisto dovesse mai accadere, sappiate che Andrea, con le sue competenze, sarà in grado di trovare una pronta soluzione senza ritrovarsi mai in difficoltà. Lasciate anche che sia lui organizzare l’itinerario, conosce bene quei porti quelle spiagge, vi guiderà in sicurezza e vi farà scoprire la bellezza di quelle coste: non resterete per niente delusi! Susanna vi accompagnerà ogni giorno con il suo sorriso e la sua gentilezza, è di Corfù e saprà prepararvi ottime colazioni ed ottimi pranzi con piatti tipici. La settimana passerà fin troppo velocemente, anche in compagnia di Mathias, il loro simpatico e quieto barboncino, mascotte della vacanza. Vi dispiacerà tornare a casa!
Valeria F.

Valeria F.

review about Cruise to the Sporades August 2017

10 / 10
Recensisco solo ora, ma segno che è rimasta nel cuore. Vacanza perfetta. Compagnia piacevolissima. Mio figlio ha avuto la compagnia del figlio di Medardo. consigliatissima!
Ana Cecilia C.

Ana Cecilia C.

review about From PATRAS to CORFOU Relaxation, seascapes and sailing get together Discover life on board! September 2019

10 / 10
Emocionada con mi primera experiencia en velero!, tuve una agradable semana en Grecia y sus bellas costas :). Claude y Genevieve siempre atentos con sus huespedes en cada detalle. 100% recomendable para una experiencia de viaje tranquila y fascinante a la vez.
Claire L.

Claire L.

review about In the sea of Ulysses, from Kefalonia sea lane to Zante July 2019

10 / 10
Prima volta in barca a vela ed è stato tutto bellissimo! Leo una garanzia e grazie a lui e la vacanza è stata ricca di avventura e risate e vento!
Brigitte S.

Brigitte S.

review about Relaxing Cruise sailing from Milos volcanic to beautiful Cyclades Minor September 2019

10 / 10
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.
Ian T.

Ian T.

review about A tasty holiday, the Dodecanese islands September 2019

10 / 10
Unforgettable, amazing experience. One of those events in life that will be talked about for many years to come. Emanuel exceeded our expectations in every way possible and he does it so effortlessly. He is an extremely competent Skipper and even though we had some rough weather whilst sailing... at times winds up to 40 knots, he was always calm and totally understood the situation at hand. He made us feel relaxed at all times. He is an accomplished chef... and I say chef... not cook, the meals he prepared were fabulous. Nothing was too much trouble for him and he always asked if things were ok for us. He is thoughtful, respectful, helpful to all, not only us on the boat, he was constantly helping other boats when they had troubles. He knows all of the secret spots in the Dodecanese which gave us some secluded undisturbed evenings away from others and protected from overnight winds. Emanuels boat is very well equipped for ALL situations .. and I have run out of lines to writ any mor
Arnaud B.

Arnaud B.

review about One week sailing around the beautiful Greek Islands September 2019

10 / 10
Nous avons passé une excellente semaine. Phil a été très accueillant et nous a fait nous sentir à l’aise tout de suite malgré nos lacunes en anglais. La cohabitation dans le bateau a été très facile. Phil a été à l'écoute de nos attentes concernant le trajet à effectuer pendant la semaine et notre volonté d’apprendre à naviguer. Nous avons ainsi pu naviguer seuls et réaliser des manœuvres sous son contrôle, si nous le voulions. Si la météo le permettait, nous nous arrêtions dans un port différent chaque jour, et nous pouvions compter sur Phil pour nous conseiller des visites ou de bons restaurants. En somme, si vous voulez passer des vacances originales, oublier votre quotidien, ne penser qu’à la mer et au vent (au moins une partie de la journée) et apprendre à naviguer sous les bons conseils d’un capitaine passionné et bienveillant, foncez ! Arnaud et Marie.
Giorgio D.

Giorgio D.

review about Kefalonia and Ithaca: 2 beautiful islands to explore with us! July 2019

8 / 10
Una bellissima vacanza all'insegna del relax e del mare. Eric è uno skipper sempre molto attento e cordiale, ed attento al comfort dei suoi ospiti. La sua barca è mantenuta in condizioni ottime. Per il resto, ottime cene in rada, esplorazioni della fantastica costa ionica greca, ripasso dei venti e delle nozioni di astronomia, e soprattutto tante risate. Grazie, e buon Vento Eric!
Marta F.

Marta F.

review about Discover the beautiful Saronic islands on a sailing yacht August 2019

10 / 10
Bravo Istvan, hai soddisfatto in pieno le nostre aspettative! Ci hai fatto divertire e sognare sulla tua barca curata nei minimi dettagli! L’anno prossimo torneremo sicuramente in vacanza con te, preparaci un itinerario rilassante e interessante!
Fabio F.

Fabio F.

review about Flotilla 10-24 August Dodecanese August 2019

10 / 10
Andrea è stato molto gentile e professionale già in fase di descrizione della vacanza settimane prima di partire, aiutandomi a capire come sarebbe stata la mia prima vacanza in barca a vela. Per tutta la vacanza mi ha addirittura spiegato tante nozioni sulla vela e sulla navigazione. Sicuramente uno skipper validissimo. Lo consiglio!
BIANCA P.

BIANCA P.

review about LAST MINUTE PRICE - Last place on board! - In the footsteps of Ulysses - on the trail of Ulysses August 2019

10 / 10
Più che uno skipper, Filippo è stato un compagno di avventura che ci ha saputo trasmettere la passione per il mare, la vela e ci ha fatto scoprire angoli nascosti tra le meravigliose isole ioniche, con il giusto equilibrio tra emozioni in veleggiata e relax tra le acque cristalline. La sua professionalità è sempre stata accompagnata dalla capacità di saper tenere unito un gruppo, calandosi nel ruolo di capitano, ma anche di amico nei momenti giusti, “musicista” e cantante nelle belle serate trascorse in rada sotto le stelle ;) Auguro a tutti la possibilità di partire con Filippo, buon vento!
Eleonora P.

Eleonora P.

review about "Sapori in Bolina" in Dodecanese - ALL INCLUSIVE in Flottiglia - LAST MINUTE DISCOUNT! August 2019

10 / 10
Claudio è uno skipper competente e affidabile. Inoltre si è rivelato una persona davvero piacevole, accogliente e positiva! La mia vacanza è andata benissimo e pertanto consiglio a tutti una vacanza con lui (e Carmen)! Grazie di tutto Claudio! A presto!
Barbara D.

Barbara D.

review about Greece - International Flotilla 2019 August 2019

10 / 10
super, we enjoy too much and Eliot ws wonderfull.
Filippo P.

Filippo P.

review about Flotilla on the routes of Ulysses in Ionian Greece - 2nd week August 2019

10 / 10
Con la sua sigaretta rollata a mano...il suo guantino da velista imbruttito...un amore per il mare che trasuda da ogni poro...l’attenzione del perfezionista Un vero velista ma con animo gentile, pronto ad ascoltare i bisogni di tutti e a farsi in 4 per assecondarli; palesemente padrone della sua barca in ogni condizione; ad majora comandante
Maja V.

Maja V.

review about Flotilla on the routes of Ulysses in Ionian Greece - 2nd week August 2019

10 / 10
As one of anonima founders, beside the fact that Pol is a great skipper, organizer and manager, most important are his skills as a DJ :) thanks to him, I've learned most important italian songs :)) he will assure and manage best parties on the beach! ..this was our second common trip and you will surely be very happy if you find yourself on his boat and company..thx Pol for all unforgettable moments in Greece, i'm looking forward to upcoming trips!
Stefano A.

Stefano A.

review about Discovering Ionian Greece August 2019

8 / 10
La mia vacanza con Daniele si è sviluppata nelle isole del Mar Ionio. Da un punto di vista della conduzione e navigazione la sensazione è sempre stata di essere in sicurezza, determinato e deciso a dare istruzioni in base alle condizioni meteo. Conosce bene la zona tanto da assecondare di volta in volta il desiderio dell'equipaggio nel scegliere tra alcune varianti di baie o di isole che proponeva. Ha fatto sentire, con la collaborazione della moglie Gabriella, fin da subito l'equipaggio parte della famiglia. Vivace ha saputo dare quel tocco di spensieratezza raccontando aneddoti personali di viaggi passati o curiosità della zona. Makiba e il suo staff, insomma, ci ha fatto passare proprio una bella settimana!
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8 reasons to choose Greece for your next sailing holidays:

  • Excellent sailing conditions throughout the year, with calmer areas and areas for more advanced sailing
  • Thousands of unique islands to explore, including some of the world’s most beautiful
  • Delicious local specialties, such as: tzatziki, tarama, moussaka, dolmades, the famous Gyros, and of some of the traditional Greek liquor Ouzo and Raki
  • Home to some of the most spectacular beauty in the Greek Isles in Santorini, Mykonos, and Ios
  • Endless sailing itineraries to be designed with your skipper
  • Immerse yourself in the regions iconic white, cubic architecture and charming fishing villages
  • Discover some of the world’s most charming coves and lagoons
  • Learn the special sirtaki dance in the area’s street festivals

The best places & specific destinations to visit during your sailing holiday in Greece:

Famous sailing areas include the Cyclades, the Saronic islands, Ionian islands, Dodecanese, Sporades, and Crete - however, there are an estimated 5,000-6,000 islands in Greece. Travelling the Greek isles by sailboat allows for full exploration of the areas treasures, that would otherwise be inaccessible. Whether you are planning to travel solo, as a couple, with friends or family, and whether you are looking for a sailboat or catamaran experience, there are numerous areas of Greece that make for perfect holidaying destinations.

Sailing holidays in Corfu

The variety of sailing in Corfu between coastal town hopping and more open water routes, make it a great destination to gather a well-rounded sailing experience. Surrounding Corfu are some smaller Ionian Islands, with striking beauty and unique wildlife ecosystems - along with the coast of Albania to the north, there is much surrounding the region to explore.

Sailing holidays in Mykonos

The area is named after the grandson of Greek god Apollo - god of music, art, and the sun - Mykonos is often described as the heart of the Cyclades, and an excellent place to observe some of the richest history and tradition in Greece. Alefkántra or 'Little Venice' in Mykonos' capital town Hóra, is a beautiful example of such history - the 18th district of the town is recognised for its unique architecture, and its relationship with the sea it is perched above.

Sailing holidays in Santorini

As a precious jewel of the Aegean, and a place of striking natural beauty, Santorini has become one of the most sort after destinations in Greece. The island is the byproduct of a volcano eruption, which explains the incredibly dramatic views over Oia town, which at sunset is a truly iconic sight to behold. With a collection of golden and red beaches, and natural springs surround the island, exploring the area by island is the only way to truly experience it.

Tips to help you to better plan for your next sailing holidays in Greece:

All you need to know about your next cruise in Greece aboard a sailboat.

When to go to Greece for a sailing holiday

Greece has a pleasant Mediterranean climate throughout the year. The temperatures become particularly pleasant from April until the end of November. The periods of July and August are relatively busy, and travellers may find that in May, June, September and October trip are particularly enjoyable for boarding a sailing or catamaran holiday. The wind is moderate, therefore, you can calmly enjoy the beauty of the islands. If you decide to travel at a busier time of the year, your localised skipper will be able to take you to places tucked away from the masses.

How long should a sailing holiday in Greece be?

The Greek archipelago is vast and it is important to choose the destination according to the available amount of time, so you can fully enjoy the experience without hurry. We recommend a minimum of two weeks to discover the Cyclades and the Dodecanese. If you have less time, we recommend looking at holidays in the Ionian, Saronic, Sporades and Crete.

Transport options to and from your holiday

Greece has many international airports including Athens, Corfu, Kos, and Kefalonia where there are budget airline options. Prices can increase significantly during school holiday periods, mainly summer in July and August. We would recommend going slightly outside of the main season in May, June, September, and October. Greece has a highly developed ferry network that connects the main islands with each other, it might be required that you use one of these ferry routes in order to reach your skipper. Your skipper will be able to advise you on the best flights and additional ferry services that might be necessary.

Sailing holidays in Greece with a family

There are some sailing destinations that are particularly suitable for family holidaying. Greece is one of these destinations. The sailing conditions are ideal and the mooring opportunities are numerous. You will easily find a deserted cove where you can find an anchor spot for the kids to have fun on the beach or shallow waters. Sailing holidays are fun for both young and old!

Sailing holidays in Greece - why you should travel with a local skipper

If you want to fully enjoy your sailing holiday in Greece in the best conditions, we recommend that you go choose a trip with a local skipper. Travelling with a skipper who has insider knowledge on the area, allows travellers to fully immerse in the pleasure and relaxation of the holiday. Where individuals on the trip wish to learn or practice their sailing skills, skippers will be there to integrate travellers into the responsibilities onboard.

The best sailing itineraries for your next holiday with a skipper in Greece

  • The big Cycladic Tour: For this trip two weeks are needed to explore this archipelago from Athens. The first part of the trip will be to explore the islands of the small Cyclades ( Kea, Siros, Tinos, and Kithnos), before heading to the archipelago of the great Cyclades (Naxos, Milos, Ios, Sifnos, and Amorgos) where there is the option to push up to Santorini. The return can be made directly to the port of Piraeus in Athens, or by first making a detour to the Saronic Islands (such as Hydra).
  • Cruise around the minor Cyclades: a very beautiful adventure, and ideal for a week or more away from the powerful Meltem that can blow during the summer months in the great Cyclades. From Athens, you could then consider exploring the beautiful Kea, Siros, Tinos, Kythnos and Serifos.
  • Discover the Ionian Islands and the Sea of ​​Ulysses: a wild and untouched archipelago that is ideal for a week of relaxation. Fiscardo, the white cliffs northwest of Ithaca, the beautiful village of Kioni and its beautiful bay, the isolated island of Atokos without forgetting to stop by Kalamos and Kastos. Lefkada is then not too far away with a final well-deserved stopover before arriving to the charming port of Sami in Kefalonia.
  • The beautiful islands of northern Corfu: get ready for an extraordinary adventure exploring the islands of Mathraki, Erikoussa and Othonoi. Deserted beaches, very few inhabited islands, splendid moorings - a destination perfect for a holiday made of serenity.
  • The magical journey to Saronic Islands sailing from Athens: a splendid region sheltered from the wind and waves for calm and pleasant island hopping. From Athens, the first step can be Hydra (famously, the island without a car). After a hike ini Leonidio, you can then reach the islands of Dokos for a BBQ on the beach at Poros, and end the voyage with a cultural stopover in Epidaurus.
  • Exploration of the Sporades: with a week at sea aboard a sailboat, you are sure to uncover some of the wonders of the Sporades. Let yourself be carried by the wind to the islands of Skiathos, Skopelos, Alonissos, Kyra Panagia, and Peristera.
  • Discovering the Dodecanese: From the island of Rhodes (the largest of the archipelago), embark on a wild sailing holiday with changing sceneries. On the agenda: hopping along the Turkish coast to reach the ruins of Bouzoukale and the charming village of Bosborum, visiting the island of Symi, the Datca Peninsula and the small port of Palamut. Finally, the island of Nisyros and its volcano make for an excellent last stop before heading back to Rhodes.

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