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Crewed yacht sailing holidays & tours in Ionian Islands

Discover more than 6 opportunities to get on board a Crewed adventure in Ionian Islands. A unique experience with a local skipper, starting at €350 a week.

6

experiences

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The world's largest marketplace for sailing holidays

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Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Crewed yacht sailing holidays & tours in Ionian Islands

101 reviews

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

03/23/2025

Matt V.

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United States

Absolutely phenomenal sailing adventure with Alessandro and Andrea! From the moment we stepped aboard in Corfu with our three children (ages 7, 10 and 12), we knew we were in expert hands. They crafted the perfect itinerary, taking us to the stunning islands of Paxos and beyond, revealing the hidden gems of Greece. Our days were filled with unforgettable experiences: hiking to ancient temples, swimming and snorkeling in pristine bays, collecting sea shells, exploring historic castles, and wandering through charming seaside towns. The boat was incredibly comfortable, making our nights as enjoyable as our days. The meals onboard were all excellent as well and the accomodations were clean and cozy. Alessandro and Andrea's hospitality was truly exceptional. They are not only skilled sailors, but also passionate guides, sharing their love for Greece with us. They even played Uno with our kids every afternoon. Their knowledge and enthusiasm made this vacation one of the best we've ever had. Thank you, Alessandro and Andrea, for showing us the most beautiful side of Greece! You are simply the best! 5 stars without a doubt.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/20/2024

Hollie D.

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Australia

Alessandro made us feel seen and safe. He is quiet knowledgeable and did his best to try ensure we were all happy. Recommend
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From Corfu sailing between turquoise sea and white beaches - hostess on board

09/17/2024

Florence D.

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Spain

It was such a wonderful experience! We sailed to some beautiful spots, with crystal-clear water and some incredible shades of turquoise. This holiday is a great way to combine some relaxation: chilling on the deck, sunbathing, reading together with some water activities: SUP, swimming and snorkeling alongside some local culture and entertainment: visiting Corfu town and charming villages, shopping, having dinner in some local restaurants, exploring further by hiking/cycling/driving a scooter on land, Enrica and Omar are the best hosts and they form such a strong partnership. They made sure everything was perfect for all the guests. We all felt totally safe on board with Omar's experience and skills and Enrica cooked some tasty and healthy meals with an Italian touch. The boat was always kept perfectly clean and cosy. I will miss falling asleep to the gentle rocking motions of the sea ! Thanks for sharing your boat with us and for all your kindness!
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Sailing WellEssere in Ionian Greece

09/14/2024

Barbara P.

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Italy

Splendido viaggio nelle isole Ionie, veleggiando nel mare cristallino in tutto relax, tra bagni, snorkeling, il suo e visitando le isole più caratteristiche. Lo skipper Fabrizio, sua moglie Sari, col gatto Kekku, accoglienti e disponibili, amano profondamente queste isole e ci hanno portato nelle baie più belle, dove ci siamo svegliati nel silenzio; ci è capitato di essere accompagnati da una tartaruga o di provare un trattamento reiki con Fabrizio. La barca è curata in ogni dettaglio e molto confortevole. La cucina vegetariana di Sari è deliziosa. Molto consigliato!

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