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.
26
experiences
4.4
Premium
Caribbean: Grenadines & Martinique
6 days - 7 nights
29 departures available
January - December
Starting from
€1,250
€1,000
Per person - min 2 pax
4.4
Caribbean: Grenadines & Martinique
20 days - 20 nights
One departure available
November - December
€3,900
Per person
4.4
Premium
Caribbean: Saint Martin
6 days - 7 nights
9 departures available
October - December
Starting from
€1,400
€1,260
Per person - min 2 pax
4.4
Premium
Caribbean: Grenadines & Martinique
9 days - 10 nights
19 departures available
June - December
Starting from
€1,680
€1,512
Per person - min 2 pax
5.0
Pacific Ocean: French Polynesia
13 days - 13 nights
One departure available
August
Starting from
€2,090
Per person
4.4
Caribbean: Grenadines & Martinique
10 days - 11 nights
One departure available
December - January
€1,590
Per person
4.4
Premium
Caribbean: Guadeloupe
6 days - 7 nights
19 departures available
June - December
Starting from
€1,125
€1,013
Per person - min 2 pax
4.4
Premium
Caribbean: Bahamas
6 days - 7 nights
9 departures available
October - December
Starting from
€1,940
Per person
5.0
Caribbean: Guadeloupe
7 days - 7 nights
5 departures available
June - August
Starting from
€1,272
Per person - min 2 pax
4.4
Premium
Thailand: Phuket, Krabi and Phi Phi Islands
7 days - 7 nights
11 departures available
June - September
Starting from
€1,785
€1,339
Per person - min 2 pax
4.4
Premium
Pacific Ocean: French Polynesia
10 days - 10 nights
14 departures available
January - December
Starting from
€2,330
€2,097
Per person - min 2 pax
4.4
Caribbean: BVI - British Virgin Islands
11 days - 11 nights
One departure available
March - April
€1,590
€1,352
Per person
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
96 reviews
ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD
06/8/2026
Daniel L.
-
US
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
05/18/2026
David B.
-
MQ
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
05/9/2026
Giorgia P.
-
IT
LAST MINUTE - April 25th and May 1st in FLOTILLA in the Seychelles
05/5/2026
Giovanni M.
-
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!
Follow us on
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
