
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.
14
experiences

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August
€920
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
9 departures available
August - October
Starting from
€1,300
€1,040
Per person

4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
Per person

4.7
Italy: Tuscany
6 days - 6 nights
One departure available
August - September
€1,041
Per person

4.8
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€750
€675
Per person

4.7
Italy: Tuscany
7 days - 6 nights
4 departures available
August - September
Starting from
€700
Per person

4.9
Super!
Italy: Tuscany
4 days - 4 nights
One departure available
September
€400
Per person

4.8
Super!
Italy: Tuscany
5 days - 4 nights
3 departures available
September
€490
€466
Per person

4.7
Italy: Tuscany
4 days - 4 nights
One departure available
September
€567
Per person

4.9
Italy: Aeolian Islands
3 days - 2 nights
7 departures available
September - October
€320
Per person
4.6
Italy: Aeolian Islands
6 days - 6 nights
One departure available
August - September
€750
Per person

4.7
Italy: Northern Sardinia
6 days - 7 nights
One departure available
September
€999
€949
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
496 reviews
Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica
08/9/2026
Martina M.
-
IT
Aeolian Islands: between sea and authentic flavours
08/8/2026
Irene S.
-
IT
Sailing cruise to the Pontine: wonders a stone's throw from Rome
08/7/2026
Manuel C.
-
IT
Discovering the Aeolian Islands Between Nature, Relaxation and Fun
08/5/2026
Andrea B.
-
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