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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

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4.8

Super!

Week in the north of Corsica, via Capraia - in company

Italy: Tuscany

7 days - 6 nights

One departure available

August

€890

Per person

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4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

3 departures available

August

Starting from

€800

Per person

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5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

6 departures available

August - November

Starting from

€500

€348

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,010

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

2 departures available

August

Starting from

€390

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure

Italy: Tuscany

6 days - 6 nights

3 departures available

July - August

Starting from

€950

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€990

Per person

Why book a holiday with Sailsquare?

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

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 - Sailboat holidays & skippered tours

18197 reviews

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Sailing from Tuscany to South Corsica

07/26/2026

Serena P.

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IT

Beautiful experience, super comfortable boat, brilliant and knowledgeable skipper took us to beautiful places and sailing with the wind in our sails ,!! To be done again bye Marco
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Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/26/2026

Benedetto R.

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IT

Great skipper Captain Dario, professional and precise in the management and management of his [hidden]. It makes you feel immediately at ease in a boat equipped with every comfort. I hope to see you again soon at sea. Fair Winds 🌬️ greetings Benedict
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Sailing adventure in the sea of Ulysses - Stewardess on board

07/26/2026

Francesco Saverio C.

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IT

I don't think it could have gone better than this. A mixture of adventure, fun and mystery that I will hardly forget! Probably the best choice at this time of my life! A round of applause to the skipper Leo and the hostess Ilda who were always present in all the needs of the guests on board with a sympathy and empathy that I still feel now! The only unexpected thing was that the fridge broke but we improvised with ice and it went great anyway! All the shades of green and blue that I have seen, the paradisiacal beaches, the lunches and dinners in joy, will haunt me in my dreams ... for a long time!

Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/26/2026

Camilla V.

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IT

Experience to be redone! A group of nice people and a professional skipper who over time has made himself loved 😂❤️ We recommend everyone a nice week in the Aeolian Islands with the [hidden].

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