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Holidays and cruises on sailboats with organized activities.

Do you love to relax but also need to stay active or pursue your greatest passions? On a sailboat, you can enjoy a week or weekend of sailing and sea, combining activities such as trekking, yoga, snorkeling, and even gastronomic tastings.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 - Holidays and cruises on sailboats with organized activities.

1313 reviews

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Sailing holiday with yoga and SUP in the Saronic islands

09/15/2025

Nina S.

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Finland

Awesome week at sea. Elias knows all the best places to go to. It was just amazing to have this possibility to enjoy yoga, sailing, swimming, Greek food & culture in a relaxing & safe way with good company. I would definetily like to do this soon again.
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Sailing holiday with yoga and SUP in the Saronic islands

08/20/2025

madelaine w.

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United Kingdom

What a fabulous trip! Everything I'd hoped for and more. A great mix of relaxation and adventure with fabulous company. It was great to learn a bit about sailing whilst exploring some beautiful islands.
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Weekend a Capraia, trekking e natura

07/21/2025

Lorena C.

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Italy

A 5 star captain who also caught and cooked an unforgettable tuna for me and the crew for my birthday! Thank you for your professionalism and availability. Until next time... fair winds
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Sailing and yoga: discovering Elba and the north of Corsica

07/21/2025

Rossella L.

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Italy

Filippo is a very prepared and helpful skipper!! He guided us in a punctual and clear way and immediately made us become familiar with the activities of the boat!! A good cook and speaker, he was able to create a good atmosphere on the boat right from the start!! Thank you Filippo until next :):)

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