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experiences

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 -

519 reviews

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Take part in the 55th Barcolana with everything included

10/11/2023

Peter C.

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Italy

Fantastica esperienza! Nonostante il vento quasi inesistente Alberto e Federica ci hanno fatto sentire tutta l'energia della Barcolana! Grazie!
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Sailing boat trip with aperitif on board!

10/9/2023

Serena F.

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Italy

Persona gradevolissima e skipper competente
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Day Trip Sailing around the Golfo Di Paradiso towards Portofino ALL INCLUSIVE - FLEXIBLE DATES

10/5/2023

Pietro R.

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Italy

Kit e sua moglie Alice sono stati degli ospiti eccezionali. Torneremo presto a trovarli.
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Free in the Wind!... perfumes and wonders in the upper Adriatic

09/25/2023

Enzo B.

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Italy

Ottimo skipper ma soprattutto bella persona; è stato un piacere passare una giornata in barca a vela con Paolo. Anche per le persone alle primissime armi è un tipo di esperienza super consigliata avendo la certezza che Paolo vi aiuterà a vivere al meglio questa diversa dimensione del mare. Buona navigazione a TUTTI

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