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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.

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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 - Holidays and cruises on sailboats with organized activities.

1282 reviews

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Trekking & Sailing Experience 25 Aprile tra Elba e Capraia - 2 barche

04/30/2024

luca f.

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Italy

Esperienza bellissima, nonostante il meteo non abbia consentito di raggiungere Capraia, lo skipper Edoardo ha organizzato con Francesco, la guida trekking, un itinerario molto divertente ed esaustivo dell'isola d'Elba. Edoardo bravo, competente e molto comunicativo, davvero una bella persona!
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

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Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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Wine Experience with Sommelier on the Island of Elba

10/4/2023

Davide Q.

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Italy

Una splendida esperienza, una crew affiatata e divertente che ha scoperto alcuni angoli suggestivi dell'Isola d'Elba e che ha potuto vivere una vera Wine-experience, tra visita in cantina, trekking in vigna, degustazioni e cena con abbinamenti. Il tutto guidato da esperti sommelier.
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All Inclusive Mallorca - Ibiza on large 18m Ketch with Insurance and Steward

10/1/2023

Stefano G.

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Italy

Purtroppo le condizioni meteo ed il mare grosso hanno un po' stravolto il programma della vacanza. Filippo e' simpatico e paziente e sa quel che fa, ponendo attenzione alla sicurezza. E' stato anche molto gentile prestandomi un suo vecchio telefono perche' avevo avuto un problema con il mio e non potevo usarlo. Ottimo il BBQ a bordo ed in generale tutto il cibo servito era molto buono.

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