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Yacht sailing holidays & skippered tours in Thailand

Discover more than 2 sailing holidays in Thailand. 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

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 - Yacht sailing holidays & skippered tours in Thailand

17 reviews

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New Year's Eve in Thailand: 10 days of magic in the Andaman Sea

01/7/2026

angelo r.

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Italy

They promised me a boat not crowded with random people, they promised me a competent skipper or at least conscious and prepared in knowing how to lead an entire crew. They promised me incredible roadsteads and dream beaches. They promised me that we would almost never go ashore and that we would wash little. In one way or another I still managed to wash myself: for the rest they were right. Left with strangers, returned with friends. Not recommended for lovers of trashy tracks, group dances, annoying drunks and Sunday skippers: because Sunday is the only day you will have to let the skipper take a nap. I would leave tomorrow.
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The charm of Thailand: let's celebrate New Year's Eve on a catamaran!

01/5/2026

Ursula C.

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Germany

Super nice tour, great support and organization. I can only warmly recommend. Gladly again
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Thailandia in catamarano: luoghi incantati da visitare!!

05/3/2025

Nuno P.

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Portugal

Wonderful week in the sea with a great group of people including Paolo the skipper. Explored beautiful islands and everything went very well. Definitely worth!
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Thailand and the Andaman Sea

03/29/2025

Vincenzo P.

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Italy

Since 2019 I have been traveling only with Sailsquare and I can say that I have never had such an intense experience as this one made with Captain Gianluca, getting to know Thailand in all its most beautiful nuances both as beaches known to few and enchanting as nature and colors and as evening and convivial locations always anchored to the culture of the place and always with unforgettable folkloristic surprises. The captain extracts from the cylinder a part of Thailand that others are precluded I have unknown, in an escalation of beauties that day by day leave you breathless. He also manages to amalgamate cruise passengers with wisdom, empathy and sympathy, creating an idyllic environment for harmony and guaranteed daily fun. An experience to FRAME. thank you for and for everything Commander Gianluca

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