header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Indian Ocean

Discover more than 3 sailing holidays in Indian Ocean. 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 Indian Ocean

82 reviews

avatar placeholder

PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

05/9/2025

Sara Angela R.

I went on a catamaran cruise with a skipper and cook, but unfortunately the experience did not live up to expectations. The destination and the proposed itinerary are truly splendid, as well as the cuisine on board, which was a highlight. The model of the boat is also very appealing, but the boat was not in optimal condition: the air conditioning worked intermittently, there was water seepage in the cabin, and overall it did not offer the promised level of comfort and luxury. The crew, especially the skipper, was cold and uncommunicative, to the point that explaining the stages or simply asking him a question seemed almost a disturbance. This made the experience on board rather flat and unengaging. In summary, despite the beauty of the places visited and the good food, the service and condition of the boat do not justify the price paid. Disappointing value for money.
avatar image

Seychelles paradise by Catamaran

05/6/2025

Fabrizio P.

-

Italy

a week on a catamaran in the Seychelles with an Italian crew is pure magic. Ciccio the captain Peppe vice-captain and Claudia the cook. Impeccable hospitality, turquoise sea and postcard beaches. Guests toooooopppppp.
avatar image

LAST MINUTE - 25 April/1 May long weekend: 4 catamarans in the Seychelles - 50% DISCOUNT

05/5/2025

Eleonora B.

-

Italy

A dream week in the Seychelles on a catamaran! There are not enough words to describe how magical this sailing holiday in the Seychelles was! A week immersed in postcard views, crystal clear waters, pristine beaches and surprising nature, all made even more special by an impeccable organization. A special thanks goes to our skipper, professional, helpful and always with a smile. He was able to guide us safely between the islands, finding wonderful coves and perfect snorkeling spots every day. But he was also a human point of reference: he shared stories, advice and created a beautiful team spirit on board. The crew with whom I shared the boat was fantastic: sunny, curious people, ready to collaborate at any time, with whom a natural feeling was immediately created. We had fun, laughed, cooked and danced under the stars... it seemed like we had always known each other. A great added value were also the other three boats of our mini-flotilla: every evening we met for an aperitif or dinner all together, creating a small floating community full of energy and good humor. Between beach parties, shore excursions and endless swims, we shared unforgettable moments with truly special people. An experience that I will carry in my heart forever. If you are looking for an authentic, relaxing and at the same time thrilling adventure, a sailing holiday in the Seychelles is simply perfect! Thank you for everything
avatar placeholder

LAST MINUTE - 25 April/1 May long weekend: 4 catamarans in the Seychelles - 50% DISCOUNT

05/5/2025

Gilda S.

-

Italy

The boat was old and kept in poor condition, not in line with what was spent. For the rest, beautiful places. I rate the holiday 3 thanks to the perfect and harmonious crew.

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964