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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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4.7

Flotilla Marmaglia Sun & Fun - Croatia

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,180

€1,080

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

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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

6 departures available

July - August

Starting from

€870

Per person

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4.5

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,134

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

5 departures available

July - September

Starting from

€600

€570

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

August - October

Starting from

€590

Per person

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4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€950

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

11 departures available

July - October

Starting from

€1,200

€1,080

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€795

Per person

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4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,110

€999

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

5 departures available

July - September

Starting from

€900

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

18017 reviews

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Kornati: the pearl of Croatia

07/11/2026

Silvia M.

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IT

Wonderful week with good winds, beautiful coves, the company and guidance of Marco!
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Let's discover the Aeolian Islands together by sailing

07/10/2026

Davide R.

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IT

Unforgettable holiday! Mario is the skipper everyone wants. He knows Aeolian Islands inside out, and everyone knows him there. Thank you for everything. I hope to see you again soon! :)
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Midweek sailing trip in the Gulf of Naples

07/10/2026

Raquel Leonor C.

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ES

Best of all, Sandro the Skipper 🇮🇹 Amazing 👌 ⭐️⭐️⭐️⭐️

Mini whale watching cruise with WWF guide between Ponza and Palmarola

07/10/2026

Anna D.

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IT

It was my first experience on a sailing boat and I can only say that I can't wait to repeat! Andrea, our guide, was very good: prepared and able to create a good atmosphere - as well as giving very interesting information. Our commander Luca was also very good. I also and above all thank the wonderful travel companions. Excellent balance between navigation, swimming in the sea, visits to the islands, studying cetaceans. Nice project!

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