Homepage cover
logo

Log in

Yacht sailing holidays & skippered tours in Greece

Discover more than 1 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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

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 - Yacht sailing holidays & skippered tours in Greece

2089 reviews

avatar image

Different flotilla in Ionian Greece: nature, new friends and fun

08/29/2026

Lucian Alexandru L.

-

IT

A memorable experience.
avatar image

Zakynthos sailing escape - hostess on board (half board)

08/29/2026

Simone U.

-

IT

The cabin crew was great, the best aspect of the whole holiday!!
avatar image

Come and try sailing in Ionian Greece

08/29/2026

Marco A.

-

IT

I could tell you about the magnificent places I visited, the good Greek food, the fantastic sunsets and beautiful sunrises, the clear, warm and wonderful water and the beautiful people I met on board the [hidden]. It would be simple, but many have already done it. Instead, I want to tell you about a person, the boat he decided to call home and what he was able to convey to me. A week is not enough to be able to say that you know a person in depth but on a boat you are tight and 10 days can make you understand a lot about a person, his passion, what makes him move, his doubts, his emotions, his fears and his strengths. If one decides to open up to others, to be read, the magic happens and even in a short time you feel somehow connected. You are sharing a piece of your life and, if you want, you can share that piece deeply. For me the boat is also this, it is emotion when you unfurl the sails and feel that force that pushes you, that you can indulge and a little force but you cannot control, it is that feeling of power under an apparent control, but it is also much more... it is sharing, it is empathy, it is laughter, it is reflection and this is allowed only by the people with whom you share those moments. If you are looking for the cool holiday to take selfies that can be taken with a spritz in your hand, forget about Angelo and [hidden]. If, on the other hand, you are looking for a real person to laugh and joke with, to be made fun of a lot, but who can really convey a passion, then this could be the right choice, and if you really want to get involved... He certainly does not back down. Good winds.

From Kalamata to Lefkada: from the Peloponnese to the Ionian Sea with Hostess on Board

08/29/2026

Alessandro F.

-

IT

Wonderful experience! Fantastic crew, sea and mythical places, total relaxation.

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964