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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!



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The world's largest marketplace for sailing holidays

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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

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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

5 reviews

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Christmas on a Catamaran in Phuket in Thailand - LAST PLACE FOR WOMEN


olivier c.



We where 11 on a boat for 10, it was ok as i like to sleep outside (didnt have so to share the bed with another guy, i was not informed of that). Susbcribing this Cruise, i expected ... to sail. Sadly we motored during 3 days (2 hours genoa with engines). At this moment we had burned half the gas-tank. the weather was sail-possible (you can check on windy), disapointing to see the waves running with boat ... ???? Finaly à left the boat the 4th Day, to change my plans. I subscribed by sailsquare, not on motorsquare. Olivier,
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Christmas on a Catamaran in Phuket in Thailand - LAST PLACE FOR WOMEN


Kirsty T.



Myself and one other left the boat early. I’m a skipper too; before joining I asked Enrico if he planned to sail or just motor. I would like to sail. He said he would sail. He did not sail once during the four days I was on board. He never got the main sail out. Only the genoa for an hour while motoring - badly trimmed. There was wind. My cabin was the size of a coffin. It was mouldy, had no a/c, and no power socket. It was a storage locker that had a shelf with a mattress installed. I paid the same as guests who had proper cabins. Enrico did not speak enough English to communicate. We were woken at 6am just to motor at 8.5 knots to moorings with murky where no one wanted to swim. Once we arrived at a nice beach, paid to enter but only had 1hr before it closed. Lack of planning. I was told I could pay less towards food as I am vegan. The others bought meat and dairy. When I arrived I was shouted at by everyone insisting I pay equally. I refused and paid less, but still paid too much.
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New Year in Thailand: 2 catamarans in Flotilla - ORGANIZED FLIGHT


chiara f.



Pepi è simpatico e disponibile e la sua organizzazione del viaggio è stata perfetta! Davvero consiglio una vacanza con lui!
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New Year in Thailand: 2 catamarans in Flotilla - ORGANIZED FLIGHT


cinzia margherita c.



ciao mi sono trovata molto bene. Giuseppe è un ottimo skipper. Consiglio a tutti questa vacanza. ciao Cinzia

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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

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