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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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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia - WOMEN SEATS ONLY - BUS INCLUDED!

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,180

€800

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

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

One departure available

August

€920

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

2 departures available

August - September

Starting from

€795

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

2 departures available

August - September

Starting from

€600

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

9 departures available

August - October

Starting from

€1,300

€1,040

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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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

August - October

Starting from

€590

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

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

2 departures available

August - September

Starting from

€900

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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.

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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

18303 reviews

Midweek getaway between Elba and Capraia

08/2/2026

Barbara B.

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IT

Beautiful experience, perfect skipper, super company, lots of nature, absolutely recommended

Leave everything for the Island of Elba

08/2/2026

Gianmarco N.

-

IT

We had a simply unforgettable experience aboard Josuah's boat. Two days that we will carry with us for a long time, between breathtaking landscapes, crystal clear sea and moments of pure relaxation. But what really made this experience special was Josuah's hospitality: an exceptional skipper, always available, attentive and able to make you feel at home from the first moment. His passion for the sea and what he does can be felt in every detail and makes the journey even more authentic. It was not just a boat trip, but an experience full of emotions, sharing and beautiful company. If you're looking for something more than just hiking, this is the way to go. Thank you very much, Josuah. We hope to return to sail with you soon!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/2/2026

Barbara U.

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IT

It was a wonderful holiday aboard Alessandro's sailboat. You can clearly perceive the passion that Alessandro and Andrea have for their boats and for the sea. The two boats sail together and it is a pleasure to see what team the two brothers form. They took us to the most beautiful beaches with crystal clear water, led us to discover small islands and villages and of the enchanting town of Corfu. They proved to be extremely competent, always friendly, attentive at all times to our safety and well-being. Carlo, the very nice steward, spoiled us with delicious meals and took us on stand-up paddle boarding. In addition, Eros and Matthias, the two four-legged friends on board made the holiday a very special experience. Even wasp stings are managed with such efficiency that they allow you to enjoy your holiday in total relaxation and safety. A thousand stars to these wonderful captains!

On board with the chef at the Egadi Islands

08/2/2026

Ilaria B.

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CH

Perfect week. Max is not only an excellent skipper, but also a passionate and talented chef who pampered us from start to finish with dishes worthy of a starred restaurant. He always advised us the best, on the boat as well as on land, careful and prudent even when we had a day of very strong wind. He made us explore the most beautiful parts of the islands. He does his job with extreme passion and always trying to make guests appreciate these wonderful islands. He also has a great deal of patience, which doesn't hurt on a boat! As a plus, the boat also has very comfortable outdoor mattresses. Finally, we happened to have a very nice group. In short, top holiday and highly recommended! Thank you Max!

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