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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

€1,070

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

6 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

4 departures available

July - September

Starting from

€795

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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4.6

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!

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

Italy: Tuscany

6 days - 7 nights

6 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

18006 reviews

Corfu between bays, taverns and myths.

07/9/2026

Loredana L.

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IT

Beautiful experience! Hansel, in addition to being a great captain, is also hospitable and attentive to every detail to make you experience a real holiday! She treated us like princesses, making us spend wonderful days in beautiful places and in total relaxation! Then I cannot fail to mention his skills as a great Chef! A truly special touch to everything was then given by our captain Leonor!!! super super super good, sweet and nice!
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Egadi Sail & Relax: the archipelago to experience

07/9/2026

Simone G.

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IT

There are trips that leave a mark that goes far beyond the beauty of the places visited. For my first experience alone, Paolo's presence was fundamental. In addition to an indisputable professionalism and an extraordinary boat, Paolo was able to convey a warmth and empathy that allowed me to experience this adventure in an authentic and profound way. It will undoubtedly be my point of reference for the future, I am happy to be able to say that this experience has given me a new and sincere Sicilian friend. This trip would not have been the same without Leonardo, Marica, Patrizia and Andrea: wonderful people who enriched every moment with their uniqueness, leaving me with a beautiful memory. It was a perfect experience in its harmony.
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Egadi Sail & Relax: the archipelago to experience

07/9/2026

Leo L.

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IT

One can only speak well of this holiday. Starting with Paolo who was very kind and super helpful since before the booking, when we asked if it was possible to change the departure and return dates. Paolo an exceptional skipper, a very capable cook, a travel companion who always makes you feel safe and at ease. It was wonderful to sail with him, he involved us all in the experience of steering his [hidden] very well kept. He made us visit beautiful corners of the archipelago, his knowledge of the places and people also allowed us to be welcomed in every place with great courtesy and also with some pluses that you only grant to friends. He was able to reassure even a travel companion at the first experience who rightly had some fears facing the sea, but in less than a day he was able to transform that fear into passion and serenity. I wouldn't change anything about the experience, apart from the duration that I didn't wish it would end so soon. I could talk about a thousand things but obviously the Egadi Islands must be discovered, not told, so if you are undecided about which skipper and boat to choose, choose Paolo and his [hidden].

Three days at the Marine Protected Area of the Tremiti Islands

07/9/2026

Dario P.

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IT

5 star experience, really recommended. We had a short sailing holiday in the Tremiti Islands with Marco as skipper and we were very satisfied. Marco is an extremely competent and helpful person, as well as a great storyteller: he told us very interesting anecdotes and history pills, with intelligence and pleasant irony. In particular, we really liked the way he introduced us to the history of the Tremiti Islands, with lightness and humor, but without losing rigor and attention to historical details. From the point of view of organization it was impeccable. He took us to the most beautiful coves, moving with great availability both with the boat and with the tender, and he always took care to make us live every moment of the day to the fullest, choosing the most suitable solutions based on the sea, the weather and our desires. It was just me and my partner, but Marco worked as if he had a large group on board with different needs: present, proactive, attentive and never intrusive. My partner and I are a bit lazy but Marco managed to move us and activate us, when we didn't have precise ideas on what to do, he proposed itineraries and activities, always managing to find the right balance between relaxation, discovery and fun. The boat was comfortable and the atmosphere on board very pleasant. It was a short holiday, but intense and well organized, which left us with a beautiful memory of the Tremiti. We recommend Marco without hesitation to those looking not only for a capable skipper, but also for a person who can really make the sea and the islands live.

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