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.
20
experiences
20
experiences
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
One departure available
August - September
€750
Per person
4.8
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
September - November
€583
Per person
4.7
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
8 departures available
August - October
Starting from
€1,100
€1,045
Per person
4.7
Italy: Tuscany
7 days - 6 nights
3 departures available
September
Starting from
€600
Per person
4.6
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
€419
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
4 departures available
September - October
Starting from
€294
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
4 departures available
September - October
Starting from
€220
Per person
4.7
Greece: Saronic Islands and Athens area
6 days - 6 nights
2 departures available
September
€585
Per person
4.9
Italy: Aeolian Islands
7 days - 7 nights
3 departures available
September - November
Starting from
€650
€585
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€350
Per person
4.6
Italy: Naples & Amalfi Coast
3 days - 3 nights
2 departures available
September
Starting from
€452
€429
Per person
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 and Catamaran Holidays for Families
337 reviews
Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew
08/29/2025
Silvia M.
-
Italy
Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms
08/28/2025
Bianca Maria R.
-
Italy
Sailing cruise to the Pontine: wonders a stone's throw from Rome
08/28/2025
Simone G.
-
Italy
Sailing cruise to the Pontine: wonders a stone's throw from Rome
08/27/2025
Manuela C.
-
Italy
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