Sailing and Catamaran Holidays for Families
Exploring the turquoise waters of the Mediterranean's most beautiful archipelagos by sailboat is a magical experience for the whole family. Each day becomes an unforgettable chapter of a sea adventure immersed in nature: children have fun exploring pristine bays, swimming with fish, learning to sail, while parents relax in complete serenity.
9
experiences
9
experiences
4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
5 departures available
September - October
Starting from
€1,100
€880
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
4 departures available
October - November
€583
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
4 departures available
September - October
Starting from
€220
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
3 departures available
October
Starting from
€294
Per person
4.7
Spain: The Balearic Islands
6 days - 7 nights
3 departures available
September - October
Starting from
€600
Per person
4.8
Italy: Tuscany
4 days - 3 nights
One departure available
September
€360
€342
Per person
5.0
Spain: The Balearic Islands
6 days - 7 nights
4 departures available
September - November
Starting from
€630
Per person
4.9
Italy: Aegadian islands
7 days - 7 nights
2 departures available
September - October
€875
Per person
4.9
Italy: Aeolian Islands
7 days - 7 nights
One departure available
November
€650
€585
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 and Catamaran Holidays for Families
377 reviews
Long weekend of whale watching with WWF guide on an 18-meter schooner
09/16/2025
Paolo S.
-
Italy
Capri LightBlue and Positano BluSKy
09/16/2025
Claudia D.
-
Italy
Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades
09/15/2025
Florian H.
-
Germany
Weekend on a sailing boat between Capraia and Elba
09/15/2025
Tamara V.
-
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 & SupportLet's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964