header cover
logo

Log in

Sailing Holidays and Catamaran Cruises to Exotic Destinations

Hidden lagoons, unnamed islands, and skies without borders: your adventure of nature, wonder, and freedom begins where the maps end. Sail through remote atolls, coral reefs, and palm trees brushing the ocean. Dive into crystal-clear waters teeming with colorful fish, explore deserted beaches, and listen to the silence of the tropics under the stars. Every bay is a new marvel. Every day, a new adventure in a dreamlike setting.

cover image
avatar image

4.7

Premium

Seychelles by Catamaran: Cabin Cruise with Full Board

Indian Ocean: Seychelles

5 days - 5 nights

One departure available

September

€1,565

Per person - min 2 pax

cover image
avatar image

4.7

Premium

Seychelles by Catamaran: Cabin Cruise with Full Board

Indian Ocean: Seychelles

7 days - 7 nights

36 departures available

January - December

Starting from

€1,760

Per person - min 2 pax

cover image
avatar image

5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

cover image
avatar image

4.4

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

64 departures available

January - December

Starting from

€1,290

€1,161

Per person - min 2 pax

cover image
avatar image

4.4

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

44 departures available

January - December

Starting from

€1,680

€1,344

Per person - min 2 pax

cover image
avatar image

4.4

Premium

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

21 departures available

January - December

Starting from

€1,520

€1,292

Per person - min 2 pax

cover image
avatar image

4.4

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

53 departures available

January - December

Starting from

€1,270

€1,143

Per person - min 2 pax

cover image
avatar image

4.4

Premium

BAHAMAS EXUMA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

6 days - 7 nights

50 departures available

January - December

Starting from

€1,815

€1,634

Per person - min 2 pax

cover image
avatar image

4.4

Premium

KOH SAMUI Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

19 departures available

May - September

Starting from

€1,885

€1,697

Per person - min 2 pax

cover image
avatar image

4.4

Premium

TAHITI - RAIATEA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

28 departures available

January - December

Starting from

€2,490

€2,241

Per person - min 2 pax

cover image
avatar image

4.4

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

40 departures available

January - December

Starting from

€1,390

Per person - min 2 pax

cover image
avatar image

4.4

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

75 departures available

January - December

Starting from

€1,535

Per person - min 2 pax

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Sailing Holidays and Catamaran Cruises to Exotic Destinations

103 reviews

avatar image

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

09/7/2026

GURMEET S.

-

US

Sailing around Martinique, St Vincent and the Grenadines, was spectacular, with excursions for a small fee highly memorable. The skipper Gerard was extremely professional, skilled, providing a smooth, flawless sail on a 54 foot, high quality, well equipped catamaran with very comfortable cabins. This experience could easily have been a 5 star rating, were it not for the one crew member dedicated to general guest services and cuisine on board. [hidden] employed someone lacking the minimum professional skills one would expect in the hospitality sector. The crew member had an indolent, disinterested and shoddy attitude, leaving guests feeling like a cumbersome burden. Simply asking politely for extra utensils or plates at meal times was met with scowls and complaints about extra washing up! The lack of hygiene on board was also unacceptable with whatever dirt that accumulated over the week inside the cabins and common areas building up. The kitchen was only superficially cleaned and on more than one occasion left flies and insects to fester. Cuisine cooked on board was generally flavourless, uninspired and even insufficient on occasion. This was frustrating when the program is full board for the week. We have travelled on other vessels with other companies and had a far better level of service for similar cost. All that said, we had a wonderful week sailing, we just would not book with this company again.

Polynesian Escape - 14 Days

08/25/2026

Chloe C.

-

CH

An absolutely fantastic experience in the Tuamotu archipelago! This sailing course was much more than a simple cruise: a real dream trip, made of navigation, discoveries, encounters and unforgettable moments. I couldn't have dreamed of a better way to discover sailing! A huge thank you to Hervé and Angela, who are simply great. Both are extremely professional, caring, very kind and always full of humor. But what makes them truly unique is also their authenticity which perfectly reflects the spirit of the cruise: simple but rich in emotions and discoveries, human, warm and far from tourist experiences. And what about the meals! Hervé and Angela cook wonderfully. I also really enjoyed the different excursions and local activities (diving, cultural activities, snorkelling, foil, etc.) they offer. They allow you to get off the beaten track, to discover Polynesia and to really immerse yourself in the culture and local life. Thanks to their excellent knowledge of Polynesia, they are always ready to offer activities if the weather changes. We had the opportunity to do several long sailings, which were among the beautiful moments of the trip: the time to really sail, to learn, to exchange and to fully enjoy life on board. It was also great to listen to the tales of their many travels and adventures, as well as Hervé's sailing experiences. Hervé also knows how to transmit his passion for sailing with patience and good humor, whatever the level of each one. The atmosphere on board was great, with extraordinary teammates who also contributed to making this adventure unique. Breathtaking landscapes, beautiful sailing, discoveries, exciting stories, laughter, a warm atmosphere and above all a deeply authentic experience: it is difficult to dream of better. I will keep an exceptional memory of this adventure and I will leave without the slightest hesitation for another cruise with Hervé and Angela. An experience that I recommend with my eyes closed!
avatar image

Polynesian Escape - 14 Days

08/24/2026

Ganesh S.

-

CH

Incredible once in a lifetime experience with Herve & Angela. Herve is a master of his craft and Angela made sure I was made comfortable during the entire trip even though I was the only non-French speaker. I highly recommend the tour and it’s a great way to learn the art of sailing from an experienced master of his craft- Herve
avatar image

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

08/24/2026

Barbara R.

-

IT

5 stars for this trip that fully met expectations, Comfortable boat, prepared and professional crew but at the same time friendly and attentive to everyone's needs. Well thought out itinerary with the right mix of activities and relaxation. The islands are beautiful with beautiful beaches!

Customer Support

customer support

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!

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