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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.

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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August - September

€750

Per person

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4.8

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years. - Live them with us.

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - November

€583

Per person

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4.7

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

8 departures available

August - October

Starting from

€1,100

€1,045

Per person

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4.7

Week between the Tuscan Islands and North Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

Starting from

€600

Per person

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4.6

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

4 departures available

September - October

Starting from

€294

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

4 departures available

September - October

Starting from

€220

Per person

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4.7

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

September

€585

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - November

Starting from

€650

€585

Per person

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4.9

Super!

Weekend on a sailing boat between Capraia and Elba

Italy: Tuscany

2 days - 2 nights

One departure available

September

€350

Per person

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4.6

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

2 departures available

September

Starting from

€452

€429

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

337 reviews

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

08/29/2025

Silvia M.

-

Italy

It was a wonderful week beyond expectations, shared with fantastic people ! An experience in total connection with nature. Paolo with his knowledge allowed us to fully experience every single day with spectacular sailings and to visit beautiful places. Vittorio great sailor person and excellent cook! I recommend to everyone, to do absolutely, there tournaments tomorrow but alas we go back to work 😔
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/28/2025

Bianca Maria R.

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Italy

An unforgettable experience on board the [hidden] with Luca and Tommaso! Luca, an experienced skipper who is always attentive, was able to read the weather conditions and build a perfect itinerary, allowing us to sail almost always and to experience each stage to the fullest. He involved us in the maneuvers and anyone who wanted to could feel like an active part of the crew: a real added value. Tommaso, in addition to being a very prepared second on board, also turned out to be an extraordinary cook: every day he delighted us with tasty and well-kept dishes, always with an eye to local products. And then the group: a mix of people with different experiences and backgrounds that made the week special. Swimming at sunset, excursions to discover the hidden corners of Corsica, SUP regattas, 40-scale tournaments, DJ sets and spritz time... Each day was unique and full of positive energy. Thanks to Luca, Tommaso and the whole team for making this adventure unforgettable! I can't wait to get back on board! 🚤⛵✨
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/28/2025

Simone G.

-

Italy

The experience with Sailsquare and with the Skipper Antonio was really nice, Giulia's assistance in completing the purchase was decisive, Antonio led us to discover secret corners of the Pontine area, showing absolute mastery of the seabed and coves of the Pontine Islands, surprising even those of us who knew the archipelago well, anchoring and sailing always in the name of maximum safety and comfort allowed, sometimes he cooked for us and turned out to be excellent and discreet company, his consolidated relationships in the docks allowed us to always have open doors, for a safe mooring when the weather required it and a privileged entrance in the Roman port of Ventotene, the islet is a real pearl of history and circumscribed beauty, finally my fellow adventurers a beautiful heterogeneous crew, a real crew devoted to joy where everyone has brought soul to the spirit of the group, compact from start to finish, Thank you you are Beautiful
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/27/2025

Manuela C.

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Italy

Very successful week, Bruno is an excellent skipper, he knows the places in depth, even if I have been going to Ponza and Palmarola for a lifetime, he made me discover things that I still did not know. He is also an excellent cook... and we were all happy about it. The crew was perfect, in short, everything fit together well. Some refinement to the boat would not be bad, starting with the tilting kitchen, but since Antonio is a craftsman he will certainly provide for next year 😉. However, I am satisfied and... fair winds to alliiiiii!!! Anto' stop, here I can't wear🤣 the shirt

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