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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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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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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€950

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€370

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

2 departures available

July - August

Starting from

€946

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

One departure available

September

€300

Per person

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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

5 departures available

August - October

€650

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

€441

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€900

€855

Per person

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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

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4.9

Super!

Weekend at the Pontine. Travel with photographer-Life changing experiences

Italy: Pontine Islands

3 days - 2 nights

3 departures available

September

Starting from

€370

€352

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€550

€495

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 - Sailboat holidays & skippered tours

17966 reviews

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Sailing in the magical Sardinia of the South

07/6/2026

CATIA B.

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IT

South-west of Sardinia to take your breath away, but the real show was on board! ⛵️ Between the beautiful sea and the regatta simulations we felt like real sea dogs (with a very high level of competition and memorable laughs!). Special praise to skipper Gianluca: not only a professional, but a saint for having resisted the barrage of questions from my 8-year-old grandson, turning him into a little sailor. The icing on the cake: exceptional company, postcard sunsets and attention to good food that made every aperitif a gourmet moment. Five stars are not enough!

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

07/6/2026

umberto v.

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IT

Efficient boat, very kind company suitable for a boat holiday.
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Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic

07/6/2026

Vitaliano T.

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IT

Wonderful experience! Antonio is a prepared and welcoming skipper, the boat adequate for the objective and the geography of the place simply fantastic. One of the most successful holidays ever 😉 Don't go, I'll be back! 🤓✌️💥

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

07/5/2026

Monica Sofia S.

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IT

It was a beautiful week, Francesco is a very prepared skipper and transmits his passion for both the sea and cooking. In my opinion it should just be clearer with the rules on board.

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