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.
38
experiences
38
experiences
5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
4 departures available
June - September
Starting from
€800
€720
Per person
5.0
Super!
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
June - September
Starting from
€935
€748
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
11 departures available
June - September
Starting from
€650
Per person
4.9
Super!
Italy: Liguria
3 days - 2 nights
11 departures available
August - October
Starting from
€220
€187
Per person
5.0
Italy: Aeolian Islands
7 days - 7 nights
5 departures available
June - November
Starting from
€650
€585
Per person
4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
7 departures available
July - October
Starting from
€294
Per person
4.7
Spain: The Balearic Islands
6 days - 7 nights
7 departures available
June - August
Starting from
€1,200
€960
Per person
4.7
Italy: Tuscany
6 days - 6 nights
5 departures available
July - September
Starting from
€1,041
€989
Per person
4.7
Italy: Liguria
5 days - 6 nights
10 departures available
June - September
Starting from
€767
€729
Per person
4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
8 departures available
July - September
Starting from
€550
€523
Per person
4.7
Italy: Tuscany
6 days - 6 nights
4 departures available
June - July
Starting from
€978
€929
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
7 departures available
July - October
€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
160 reviews
2 June: whale watching expedition with WWF guide in Liguria
06/10/2025
cristina g.
-
Italy
Capri LightBlue and Positano BluSKy
06/10/2025
Simone D.
-
Canada
2 June: Whale watching expedition with WWF guide between the Amalfi Coast, Ischia and Capri
06/9/2025
Hayley F.
-
United Kingdom
Long weekend of whale watching with WWF guide between Golfo Paradiso and Gulf of Tigullio
06/9/2025
Gianmarco G.
-
Italy
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