Holidays and Sailing Cruises by Sailboat and Catamaran in Saint Martin
Set off on the sailing cruise of your dreams to discover the pearl of the Caribbean. Treat yourself to a holiday among hidden bays, colorful markets, and Caribbean rhythms. Golden sandy beaches, turquoise waters, breathtaking views, and steady winds await you — perfect for experiencing this paradise under sail.
3
experiences
3
experiences
4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
51 departures available
January - December
Starting from
€1,125
€1,013
Per person
4.3
Premium
Caribbean: Saint Martin
6 days - 7 nights
One departure available
January
Starting from
€2,690
Per person - min 2 pax
5.0
Caribbean: Saint Martin
11 days - 11 nights
3 departures available
March - April
€1,795
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 - Holidays and Sailing Cruises by Sailboat and Catamaran in Saint Martin
9 reviews
12 day Cruising/Sailing Experience around St. Martin and St. Barth's
04/17/2025
Basiel B.
-
United States
7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board
03/28/2023
Thomas T.
-
Austria
7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board
03/27/2023
Emanuel R.
Caribbean sailing cruise in St. Martin - Anguilla
02/22/2020
Carla P.
-
Italy
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 2035144220Read our
Contact & SupportSaint Martin: the best travel ideas
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964