
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.
21
experiences

4.7
Premium
Indian Ocean: Seychelles
5 days - 5 nights
One departure available
September
€1,565
Per person - min 2 pax

4.7
Premium
Indian Ocean: Seychelles
7 days - 7 nights
36 departures available
January - December
Starting from
€1,760
Per person - min 2 pax

5.0
Super!
Pacific Ocean: French Polynesia
13 days - 13 nights
One departure available
October - November
€2,090
Per person

4.4
Premium
Caribbean: Grenadines & Martinique
6 days - 7 nights
64 departures available
January - December
Starting from
€1,290
€1,161
Per person - min 2 pax

4.4
Premium
Caribbean: Grenadines & Martinique
9 days - 10 nights
44 departures available
January - December
Starting from
€1,680
€1,344
Per person - min 2 pax

4.4
Premium
Caribbean: Saint Martin
6 days - 7 nights
21 departures available
January - December
Starting from
€1,520
€1,292
Per person - min 2 pax

4.4
Premium
Caribbean: Guadeloupe
6 days - 7 nights
53 departures available
January - December
Starting from
€1,270
€1,143
Per person - min 2 pax

4.4
Premium
Caribbean: Bahamas
6 days - 7 nights
50 departures available
January - December
Starting from
€1,815
€1,634
Per person - min 2 pax

4.4
Premium
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

4.4
Premium
Pacific Ocean: French Polynesia
10 days - 10 nights
28 departures available
January - December
Starting from
€2,490
€2,241
Per person - min 2 pax

4.4
Premium
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

4.4
Premium
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
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
09/7/2026
GURMEET S.
-
US
Polynesian Escape - 14 Days
08/25/2026
Chloe C.
-
CH
Polynesian Escape - 14 Days
08/24/2026
Ganesh S.
-
CH
ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD
08/24/2026
Barbara R.
-
IT
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!
Call us at
+44 20 3514 4220Read our
Contact & SupportLet's talk Sailsquare!



Secure payments



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