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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!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

5 departures available

September - November

€250

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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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

2 departures available

July - September

€740

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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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

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!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

2 departures available

July - September

Starting from

€200

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

14 departures available

July - November

Starting from

€600

€540

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

9 departures available

July - September

Starting from

€700

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

17838 reviews

Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/22/2026

daniela m.

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IT

I gave this experience to my husband who had dreamed of steering a sailboat for years and was satisfied! Stefano was super kind and helpful in advising me in the best possible way when and how to book and the experience itself was very nice

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

06/22/2026

Angelica C.

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IT

A weekend on a sailing boat in Ponza that was just PERFECT from every point of view 🌊⛵️ I can only congratulate our skipper Matteo, who proved to be not only extremely professional, but also incredibly attentive to every detail. The organization was impeccable: everything was planned with precision, but at the same time with that lightness that makes you feel immediately on vacation, without worries. The boat then... wonderful! Clean, well-kept and super welcoming, you can clearly see how much love and passion are behind it. I felt pampered from start to finish, almost like being in the family and not just like a customer. And the surprises? Truly unforgettable! I had NEVER seen a barbecue on a sailboat: a special lunch, in the middle of the sea, with the scent of the grill... something magical. And as if that were not enough, waking up on Sunday with fresh croissants was the icing on the cake 🥐✨ A gesture that encompasses all the care and attention that the skipper dedicates to his guests. It was an experience that I would do a thousand times over and that I recommend to anyone who wants to experience Ponza in an authentic, relaxing and at the same time special way. Thank you very much for this unforgettable weekend! 💙

All-Inclusive Sailing: Capri, Positano, Amalfi

06/22/2026

Maria Grazia I.

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IT

They were enchanting days. Natural landscapes and enchanting locations. We filled our eyes with so much beauty, unforgettable baths and sunshine. Alessandro, the skipper, wonderful. With organization and skill he allowed us to make the most of the various days. And finally he prepared some really delicious menus to eat on the boat. To sum up :SUPER☺️
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Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

06/22/2026

Elisa M.

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IT

Wonderful experience. Beautiful sea accompanied by the Skipper Salvatore who was able to guarantee a good atmosphere, safety in the enjoyment of the experiences. Together with Salvatore we were also accompanied by his wife Elisabetta, an empathetic and intelligent woman who increased the pleasantness of the experience! See you next time

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