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.
32
experiences
32
experiences
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
One departure available
August
€900
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
2 departures available
August - October
Starting from
€200
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
4 departures available
August - September
Starting from
€650
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
July - August
Starting from
€935
€748
Per person
4.7
Italy: Tuscany
6 days - 6 nights
3 departures available
August - September
Starting from
€1,041
€989
Per person
5.0
Italy: Aeolian Islands
7 days - 7 nights
2 departures available
September - November
Starting from
€650
€585
Per person
4.7
Italy: Tuscany
6 days - 7 nights
7 departures available
July - September
Starting from
€1,041
€989
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
7 departures available
July - September
Starting from
€550
Per person
4.7
Spain: The Balearic Islands
6 days - 7 nights
3 departures available
July - August
Starting from
€1,200
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
4 departures available
September - October
Starting from
€294
Per person
4.7
Italy: Liguria
5 days - 6 nights
4 departures available
July - September
Starting from
€830
€789
Per person
4.7
Italy: Tuscany
3 days - 3 nights
3 departures available
September
Starting from
€420
€399
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
210 reviews
Whale watching mini-cruise with WWF guide between Liguria and the French Riviera
07/15/2025
Tecla V.
-
Italy
Whale watching mini-cruise with WWF guide between Liguria and the French Riviera
07/14/2025
Valentina D.
-
Italy
Week between the Tuscan Islands and North Corsica
07/14/2025
Flavia G.
-
Italy
Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms
07/14/2025
Francesca N.
-
Italy
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