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Yacht sailing holidays & skippered tours in Thailand

Discover the most exotic places in the Far East: Phuket, Krabi, Koh Samui and the Phi Phi Islands. Enjoy an authentic tropical paradise and explore the 7 Wonders of Thailand!

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

15 reviews

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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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ANDAMAN Dream Premium - Catamaran Cruise with Hostess FULL BOARD

02/20/2025

Delphine G.

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France

We are very disappointed (and angry) with our cruise. The price is not at all in line with the quality and service offered. 😡😡😡😡 We booked an 11 day Thailand cruise with Sailsquare. When we made our reservation, I had read several comments about a problem with the "toilets". So I asked Giulia, the representative of Sailsquare, for details on this subject. From there, she told me that everything was resolved. But I confirm that it is not. WE SPENT 11 DAYS WITH A TOILET FILLED WITH FECES NEXT TO OUR BED. It is impossible to sleep with the door closed. We had to spend our entire stay with the windows and doors open to dampen the smell a little. Inadmissible!!! When we returned, I wanted to contact Sailsquare through Giulia, to discuss our problem but IMPOSSIBLE. I've been trying to reach them for more than 10 days but without success. They no longer respond. The after-sales service is therefore simply non-existent. At 6000€ for 11 days, we didn't expect that. 😡😡😡😡😡😡
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PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

02/18/2025

Simon E.

Brilliant cruise on the catamaran to Bond island and The Beach and favourite location being the small PAE island when the tide revealed the beach. Excellent overnight anchorages between the amazing sunsets and sunrises. Really well organised and great crew and food. Simon

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6 reasons to choose Thailand for your next sailing holidays:

  • East Asia’s tropical climate means that you can visit Thailand all throughout the year. However, if you’d prefer to avoid Thailand’s more rainy season you may want to consider visiting between November and March.
  • Thailand is widely considered one of the world’s best places for diving and snorkelling. Its stunning seabeds are home to countless species of marine life.
  • Thai food! Experience delicious native Thai dishes, made locally.
  • The coastal regions of Thailand are graced with many wild islands, virtually untouched by time or humanity. These secret islands and coves make for delightful anchorages to peacefully enjoy the magic of the landscape.
  • The country is steeped in history and rich in culture. You can find a great number of stunning Buddhist temples such as the Wat Arun, Wat Rong Khun (White Temple), Wat Phra Kaew (Temple of the Emerald Buddha), and Wat Pho (Temple of the Reclining Buddha).
  • With a local skipper discover and explore the hidden or lesser known destinations of Thailand.

The best places & specific destinations to visit during your sailing holiday in Thailand:

Thailand, sometimes known as the Land of Smiles, is adored across the world. Its stunning landscapes, natural beauty, historic monuments and temples, its rich cuisine, and perhaps most importantly the friendly and helpful nature of the local people have all come together to establish this title.

Sailing holidays in Phuket

The largest island in Thailand. Here you can find some of the most beautiful beaches in the country, including Koh Phi Phi and Koh Lanta. However, if you would like to discover an authentic jewel and enjoy a more hidden and less well-known beach, we recommend visiting Banana Rock beach. If you venture to the city of Phuket, you will have the opportunity to meet the Big Buddha, located on top of a mountain from which you can enjoy extraordinary views of the island. As for temples, you cannot forget to visit the picturesque Wat Chalong Temple, the most famous in the city.

Sailing holidays in Krabi

From Krabi it is possible to visit some of the best destinations that are only accessible by boat, such as for Railay Bay! You can continue your tour visiting Las 4 Islas, with the paradisiacal beaches of crystal clear waters and fine white sand. The 4 Islands form an extraordinary landscape at low tide, causing the four islands to end up joined by corridors of white sand. Another place to discover during one of your boat trips, is the Koh Phi Phi archipelago, formed by five paradise islands. Here you can enjoy snorkeling or diving ì with the rest of your crew. Finally, we recommend Hong Island, perhaps one of the most beautiful beaches in Krabi.

You will find beautiful buildings such as the Temple of the Tigers, where after a steep climb to the summit you are rewarded with a breathtaking view. If you are passionate about hiking and adventure, the Khao Sok National Park, one of the oldest national parks in the world, where there is much exploring to be done.

Sailing holidays in Phi Phi Islands

As a precious jewel of the Aegean, and a place of striking natural beauty, Santorini has become one of the most sort after destinations in Greece. The island is the byproduct of a volcano eruption, which explains the incredibly dramatic views over Oia town, which at sunset is a truly iconic sight to behold. With a collection of golden and red beaches, and natural springs surround the island, exploring the area by island is the only way to truly experience it.

Tips to help you to better plan for your next sailing holidays in Thailand:

All you need to know about your next cruise in Thailand aboard a sailboat.

When to go to Thailand for a sailing holiday

The best period to travel to Thailand is from January to August. There are, however, generally favourable conditions in Thailand throughout the whole year, so you can find sailing experiences outside of this period.

Holiday prices

Travelling to Thailand by boat is not as expensive as you may think, and is competitive with more conventional holidaying. You will find experiences in luxury catamarans from €1,000 per week.

Transport options to and from your holiday

Bangkok is well connected with the world, you can for example find direct flights from London to Bangkok with both Thai Airways and British Airways. Phuket, Krabi, and Koh Samui also have international airports. We recommend the use of a flight comparison site, in order to find flights that suit your requirements and budget.

Sailing in Thailand solo, as a couple, or with friends and family

Whether you’re looking for options for couples, a whole boat booking for families and groups of friends, or options for solo travellers there are different experiences to suit you. Be it a trip aboard a sailboat or catamaran, you can book one or multiple spots onboard without having to form your own group of travellers. Find like-minded people and return home with new friends!

The best sailing itineraries for your next holiday with a skipper in Thailand

  • Phuket - Ko Phi Phi Lee - Ko Lanta Yai - Ko Muk - Ko Rok Islands - Phi Phi Islands - Krabi - Ko Hong: As a first sailing experience we recommend you take this itinerary with an average duration of 9 days. You can visit the most popular places from Thailand as well as more hidden ones, you will have time for a little bit of everything!
  • Phuket - Phang Nga - Koh Hong - Koh Phak Bla - Railay Beach (Krabi) - Koh Lanta - Koh Muk - Emerald Cave - Koh Kradan - Koh Rok - Koh Ha - Koh Phi Phi - Maya Beach: If you would prefer to make your route through Thailand a little more tranquil, this itinerary is more complete and would take around 2 weeks to complete.

Thailand: the most beautiful places to sail

Thailand: departures by month

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