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
49
experiences
4.5
Italy: Aeolian Islands
From Jul 4 to Jul 11
+3
1 spots left
€620
Per person
4.7
Italy: Tuscany
From Jul 4 to Jul 11
+6
1 spots left
€970
Per person
4.8
Super!
Italy: Northern Sardinia
From Jul 4 to Jul 11
4 people
have already booked
€820
Per person
4.8
Super!
Italy: Northern Sardinia
From Jul 4 to Jul 11
4 people
have already booked
€670
€603
Per person
4.4
France: French Riviera and Porquerolles
From Jul 4 to Jul 11
5 people
have already booked
€730
Per person
4.8
Italy: Northern Sardinia
From Jul 4 to Jul 11
5 people
have already booked
€950
Per person
4.6
Spain: The Balearic Islands
From Jul 5 to Jul 11
5 people
have already booked
€950
Per person
4.4
Greece: Saronic Islands and Athens area
From Jul 11 to Jul 18
3 people
have already booked
€660
Per person
4.8
Super!
Italy: Northern Sardinia
From Jul 11 to Jul 18
7 people
have already booked
€870
Per person
5.0
Super!
Italy: Aegadian islands
From Jul 18 to Jul 25
+3
2 spots left
€850
Per person
5.0
Italy: Aeolian Islands
From Jul 18 to Jul 25
+6
1 spots left
€700
Per person
4.8
Super!
Italy: Northern Sardinia
From Jul 18 to Jul 25
+4
1 spots left
€750
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 holidays: how they work, how much they cost, where you can go
Where to travel
The Caribbean archipelago by sailboat
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 holidays: how they work, how much they cost, where you can go
Where to travel
The Caribbean archipelago by sailboat
Let's talk Sailsquare!
Follow us on
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964