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Perfect sailing vacations for families

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

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

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!

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

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9+

Show all

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4.6

The tropical paradise par excellence The Seychelles 25 April 2026

Indian Ocean: Seychelles

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From Apr 25 to May 2

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+3

2 spots left

€1,650

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

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From May 16 to May 23

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Jean and Stéphane

have already booked

€990

Per person

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5.0

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

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From Jun 6 to Jun 13

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+1

2 spots left

€650

Per person

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4.9

Super!

Sailing Sporades: A Green Paradise in the Heart of the Aegean

Greece: Sporades

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From Jun 6 to Jun 13

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+1

2 spots left

€890

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

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From Jun 20 to Jun 27

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+2

1 spots left

€990

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

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From Jun 20 to Jun 27

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+4

2 spots left

€1,300

€1,170

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

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From Jun 21 to Jun 28

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4 people

have already booked

€790

€751

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

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From Jun 27 to Jul 4

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4 people

have already booked

€650

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

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From Jun 27 to Jul 4

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3 people

have already booked

€770

Per person

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4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

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From Jul 4 to Jul 11

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+3

2 spots left

€2,500

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

,

From Jul 4 to Jul 11

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4 people

have already booked

€670

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

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From Jul 4 to Jul 11

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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!

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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

Whale watching sailing cruises  with WWF

Travel ideas

Whale watching sailing cruises  with WWF

Croatia by sailboat

Where to travel

Croatia by sailboat

Greece by sailboat

Where to travel

Greece by sailboat

The Aeolian Islands on a sailboat

Where to travel

The Aeolian Islands on a sailboat

Catamaran vacations

Travel ideas

Catamaran vacations

The Caribbean archipelago by sailboat

Where to travel

The Caribbean archipelago by sailboat

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