
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.
32
experiences

4.5
Premium
Caribbean: Grenadines & Martinique
6 days - 7 nights
35 departures available
May - December
Starting from
€1,099
Per person - min 2 pax

4.5
Premium
Caribbean: Saint Martin
6 days - 7 nights
25 departures available
May - December
Starting from
€1,205
€1,085
Per person - min 2 pax

4.5
Premium
Caribbean: Grenadines & Martinique
9 days - 10 nights
23 departures available
May - December
Starting from
€1,680
€1,512
Per person - min 2 pax

5.0
Pacific Ocean: French Polynesia
20 days - 20 nights
One departure available
May - June
€3,150
Per person

4.4
Caribbean: Grenadines & Martinique
20 days - 20 nights
One departure available
November - December
€3,900
Per person

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

5.0
Indian Ocean: Seychelles
11 days - 11 nights
2 departures available
May - June
€2,400
Per person

4.5
Premium
Caribbean: Guadeloupe
6 days - 7 nights
25 departures available
May - December
Starting from
€1,125
€1,013
Per person - min 2 pax

4.5
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
9 departures available
May - August
Starting from
€1,272
Per person - min 2 pax

4.5
Premium
Thailand: Phuket, Krabi and Phi Phi Islands
7 days - 7 nights
17 departures available
May - September
Starting from
€1,785
€1,339
Per person - min 2 pax
Why book a holiday with Sailsquare?
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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
89 reviews
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
04/16/2026
DONATELLA D.
-
Italy
ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD
04/3/2026
gulce c.
-
Türkiye
GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD
03/31/2026
Roberto C.
-
Italy
Under the Caribbean sun on a catamaran
03/10/2026
Irene B.
-
Italy
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