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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

4 departures available

August

Starting from

€920

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

6 days - 7 nights

10 departures available

August - October

Starting from

€1,400

€1,120

Per person

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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - September

Starting from

€600

€570

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

One departure available

August - September

€1,041

Per person

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4.7

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

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

August - September

Starting from

€700

Per person

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4.8

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

August - September

Starting from

€400

€360

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€750

€675

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€690

€613

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

One departure available

July - August

€946

Per person

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4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

2 departures available

September

€609

€579

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

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

449 reviews

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

07/25/2026

Cristian P.

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IT

Luca and Tommy super!! 😊

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

Francesca C.

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IT

It was an unforgettable experience, perfect from every point of view. The skipper is impeccable, an excellent cook and knows the sea and the Pontine islands perfectly. He is very nice and a person of heart. It is a trip that I recommend to anyone, even those who are at their first experience on a boat, like me. In addition, the places are magnificent and you will love them. Super recommended 😻
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

marco s.

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IT

If you have a city, a job and things waiting for you, don't go. Between sun, sea, food and the wonderful company of Antonio, with his kindness, generosity and stories you will never want to go home.
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

Luigi F.

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IT

We spent an unforgettable week with a varied but very nice crew! Antonio is a super skipper. He has passion, experience and is a great entertainer as well as an excellent chef. Always available he really made us discover the beauties of these wonderful islands. The boat is large, a bit dated but well maintained and always clean. Super recommended experience.

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