
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.
12
experiences

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
10 departures available
July - October
Starting from
€1,100
€1,045
Per person

4.8
Super!
Italy: Northern Sardinia
6 days - 7 nights
14 departures available
June - September
Starting from
€625
Per person

4.9
Super!
Italy: Tuscany
5 days - 5 nights
4 departures available
June - September
€350
Per person

5.0
Super!
Italy: Aegadian islands
7 days - 7 nights
6 departures available
June - September
Starting from
€800
€720
Per person

4.8
Super!
Italy: Naples & Amalfi Coast
3 days - 2 nights
5 departures available
April - September
Starting from
€272
Per person

4.8
Italy: Tuscany
4 days - 3 nights
12 departures available
June - September
Starting from
€430
€409
Per person

4.8
Italy: Tuscany
4 days - 4 nights
8 departures available
June - July
Starting from
€490
Per person

4.5
Greece: Cyclades
6 days - 6 nights
2 departures available
April - May
€990
Per person

4.9
Italy: Aeolian Islands
7 days - 7 nights
One departure available
November
€650
Per person

5.0
Croatia: Istrian peninsula
7 days - 7 nights
3 departures available
July - August
€900
Per person

4.9
Italy: Liguria
1 day - 0 nights
9 departures available
June - August
€86
Per person

4.6
Italy: Tuscany
7 days - 6 nights
11 departures available
June - September
Starting from
€750
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
400 reviews
IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper
10/25/2025
Sara C.
-
Italy
We have known the Aeolian Islands for 20 years. - Live them with us.
10/20/2025
Marco F.
-
Italy
IBIZA and FORMENTERA - ALL INCLUSIVE - on 18m ketch with skipper
10/15/2025
Cinzia R.
-
Italy
Poetic Gulf of Poets
10/9/2025
Massimo G.
-
Italy
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