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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!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

10 departures available

June - September

Starting from

€700

Per person

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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

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

July - October

Starting from

€590

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

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

€1,300

€1,170

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,070

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

8 departures available

July - September

Starting from

€600

€570

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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4.7

Marmaglia mini-flotilla: discovering the Kornati Islands

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,140

€1,040

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

2 departures available

August

€1,110

€999

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

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

17888 reviews

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Discover the Egadi Paradise by sailboat from San Vito Lo Capo

06/28/2026

Vanessa B.

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IT

It was a dream vacation!! Jo and Andrea are two treasures who have satisfied us in everything!! I have never seen such a clean boat! We went to sleep in the cabin with nothing under our feet! The good wind accompanied us with lots of laughter, good fresh food and beautiful refreshing baths!! Thank you so much for this wonderful holiday and I recommend this trip to everyone!!

Short Week at the Egadi Islands between Nature, Relaxation and Fun

06/28/2026

Dario D.

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IT

A sailing cruise much more than just a holiday, an authentic, relaxing and exciting experience. Much of the credit goes to skipper Davide, a competent person, helpful and able to convey confidence at all times. Its great experience at sea is immediately perceived and allows you to experience navigation with serenity, simply letting yourself be carried away by the beauty of the journey around the Egadi islands, simply gorgeous! In addition to being an excellent Captain, he also proved to be an amazing cook, transforming meals on board into true moments of conviviality. The combination of professionalism, passion for the sea and talent in the kitchen made this cruise truly special. An experience that I recommend without hesitation to those who want to discover the pleasure of sailing, feel welcomed like family and enjoy the sea in an authentic way. Thanks to all the crew for the great company and in particular to Davide for the wonderful experience!
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Discovering the Island of Elba: 3 days of sea, wind and sun

06/28/2026

Marco F.

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IT

Three days in Elba, starting on June 18th. What can I say, nice experience. The skipper was very helpful and competent, you can see that he is in love with his boat and cares a lot. Perhaps sometimes a little too present in the management on board, but it is clear that he does it because for him the boat comes first! The boat is always clean, tidy and comfortable. We were able to sail two afternoons when the wind allowed it, and when you really sail it's a whole different story. The top moments? The fireworks on the second evening in Marina di Campo — seen from the water are another thing — and the swim around the Pomonte Wreck, surreal swimming there. Recommended.
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Discover the Egadi Paradise by sailboat from San Vito Lo Capo

06/28/2026

Antonio D.

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BE

It was not a simple holiday, it was an unclassifiable sensory experience. It is impossible to give an evaluation of what my wife and I experienced in the company of Jo and Andrea, with Rossella, Pilar, Eric and Vanessa on board the [hidden]. Discover the Egadi Islands, listen to the sound of the sea, the smell of the wind, the colors of the sea and the views that mother nature has given us, feel the warm embrace of the sun while savoring the exquisite food together with this large family. Because this was a FAMILY, a perfect fit like the well-oiled gears of a watch. We experienced the best holiday of our lives and certainly in the future we will do it again with them because Andrea and Jo with all the rest of the crew, were INCREDIBLY FANTASTIC. Absolutely choose Jo and Andrea! THEY ARE THE BEST EVER 🏆🥇 Viva [hidden], Viva Noi ❤️🌊⛵✨☀️

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