
What to know before you go sailing with your family?
To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
Still a somewhat unusual idea, but perfect for a family vacation that everyone can agree on. A skippered cruise on a sailboat or catamaran is ideal for keeping your children happy and spending a beach vacation away from the beaten tourist spots, in complete freedom and without stress.
Where to go? You can choose Italy of course, perhaps the island of Elba and the Tuscan archipelago or Sicily, but also Croatia, with weather conditions that are always pleasant in summer, or the larger islands of Greece such as Crete, Kefalonia and Corfu, which are convenient to reach and have all the facilities. And if you want to go step by step-why not start with a trial weekend?
What to expect from a family boating vacation with your children

Perfect for young and old
On a boat, the whole family enjoys unprecedented experiences in contact with nature, far from the crush of summer resorts. The skipper is a guarantee of a smooth cruise and will do everything possible to make sure the vacation meets your family needs. So parents can relax and unplug, while the younger ones have fun, including diving, water sports and new discoveries...they certainly won't have time to get bored during a family sailing vacation!

At school for sustainability
A sailing vacation for children and young people can turn into an important experience to get closer to nature, understand how to live in tune with it and how to respect it. The intelligent use of water and energy while sailing, the need to limit waste and adapt to weather and sea conditions will leave a mark on the sensitive souls of the little ones.

Unexpected goodbye!
Sailsquare provides maximum flexibility with its policies that allow for extended refund terms, with which you can cancel up to 24h before departure! You can also pay a deposit to reserve the vacation you prefer, and then finalize the payment just before departure.
An unforgettable experience for all the family




9+
Show all
40
experiences

4.6
Indian Ocean: Seychelles
From Apr 25 to May 2
+3
2 spots left
€1,650
Per person

4.9
Greece: Cyclades
From May 16 to May 23
Jean and Stéphane
have already booked
€990
Per person

5.0
Greece: Ionian Islands
From Jun 6 to Jun 13
+1
2 spots left
€650
Per person
4.9
Super!
Greece: Sporades
From Jun 6 to Jun 13
+1
2 spots left
€890
Per person

4.9
Greece: Cyclades
From Jun 20 to Jun 27
+2
1 spots left
€990
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
From Jun 20 to Jun 27
+4
2 spots left
€1,300
€1,170
Per person

5.0
Super!
Italy: Southern Sardinia
From Jun 21 to Jun 28
4 people
have already booked
€790
€751
Per person

4.8
Super!
Italy: Northern Sardinia
From Jun 27 to Jul 4
4 people
have already booked
€650
Per person

4.8
Super!
Italy: Northern Sardinia
From Jun 27 to Jul 4
3 people
have already booked
€770
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
From Jul 4 to Jul 11
+3
2 spots left
€2,500
Per person

4.8
Super!
Italy: Northern Sardinia
From Jul 4 to Jul 11
4 people
have already booked
€670
Per person

4.8
Super!
Italy: Northern Sardinia
From Jul 4 to Jul 11
3 people
have already booked
€950
Per person
8 reasons to choose a family sailing vacation with your children
It is a unique, unforgettable experience for everyone.
The boat can be chartered exclusively for total freedom of choice on the pace of the vacation.
No more crowds and stress: enjoy the day on the deck while the kids compete in diving contests and explore the seabed with mask and snorkel.
Sailing is a very comfortable way to travel with your children, discovering other countries and cultures.
Relying on an experienced skipper for the route and stages means safe sailing.
A boat vacation will be a real adventure for children, but also a special opportunity to get closer to nature.
Take the helm with the children and let them feel how the boat responds to their orders-the passion of a lifetime could be born!
Moor offshore and sail to an island with a dinghy-nothing better to play explorer!

Travel stories
5 children, a dad, a mum and a skipper. Wondering what a family holiday on a sailing boat is like?
FAQ
Guides & tips

Travel ideas
Whale watching sailing cruises with WWF

Where to travel
Croatia by sailboat

Where to travel
Greece by sailboat

Where to travel
The Aeolian Islands on a sailboat

Travel ideas
Catamaran vacations

Where to travel
The Caribbean archipelago by sailboat
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