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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

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Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

6 departures available

September - October

Starting from

€1,300

€1,040

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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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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5.0

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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5.0

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Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

€490

€441

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

3 departures available

September

Starting from

€441

€419

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€675

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

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.

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

18928 reviews

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Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

08/30/2026

Daniela M.

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IT

A very positive week. [hidden] organized everything in detail and the skipper, in the person of Manuel Sassi, an exemplary person: very prepared and very convivial. Unfortunately the weather was not favorable but everything went well. With the same people I hope to participate in the next events.
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Sailing week between Sporades, Euboea and Volos - 2 boats in company

08/30/2026

Fabio C.

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IT

Alessandro and Pier the two skippers and Eliana and Nicoletta, are very professional and made the holiday unforgettable
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Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

08/30/2026

Bettina C.

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IT

A first experience on a sailing boat, and it was simply wonderful! A fantastic group, perfect weather, crystal clear waters and an exceptional skipper, always a great host and guide. Fair winds!
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Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

08/30/2026

Vincenzo D.

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IT

When they arrived on the spot, skipper Alessandro Sicania did not answer the phone. At 5 pm in the African heat in Marsala he made us leave our bags semi-unattended in the pier. He then makes us sign a contract with his sole proprietorship Sicania Sail (it never happened to me when I booked with SS, which is the only contractual counterpart to me) a contract that he does not give us a copy of but of which, even if forbidden, he allows me to take photos at my request. To the payment of the "service pack" (130€) which included 'towels / sheets and diesel (which is not insignificant in theory, but then we will see ..). I tell him that at the moment I only had 125 and that I would give him the other 5 later. He replies 'you take care of your own business and I take care of mine'. You give me 140 and I give you back 10 minutes. And so it was done, as per the first Order of the Commander. It is decided € 100 per person for the common fund / initial galley. It is noted that in addition to the 6 of us SS there was a 7th, Bengali but also British, which we later discover to be Alessandro's companion, who had registered her on SS independently. Even if someone else had turned up their noses from the beginning, no problem at least for me, indeed positive for English practice. However, it should be noted that the galley was included only for the skipper and so, although not without reluctance, he puts his share for her. The 6 of us SS are going to make a galley, after a list prepared in the municipality. Upon returning from the galley Alessandro begins to shout because according to him we would have been late (he had to go to sleep or anyway do something else with his partner at his house because apparently that's how he uses to do on Saturday nights) and because we would have taken only 5 cases of water. I answer him that 5 x 6 x 2lt makes 60 liters and as hot as it is, considering that Tuesday evening at the latest we would have been in port and there were also other drinks (Coca etc) would have been enough and that anyway I would have taken care (even with a tear to the quadriceps), to go and get them (as it turned out) and if they would have run out before there would still have been the tender. There too he starts and says "you have to do what I say!". Forbidden by the ras style tone of the neighborhood, tired of having run throughout the Decò megastore and in the afternoon to carry hand bags even for third parties, I allow myself to sit on the bench with S. who suffers from a pathology that does not allow him to make too much effort and we let him carry the bags on the boat since Decò had delivered them for free on the quay given the 706€ and broken shopping done. He greets us. Someone calls him back, I don't remember why. No answer. Amazing hood. With the help of S., the only other male, I move the upper awning (it was night) and the front one to let air through. We have dinner. The next morning I leave the cabin and Alessandro comes up to me and says: "you don't have to take initiatives you understand????". Don't allow yourself to take initiatives on my boat anymore! Because otherwise I'll let you disembark!" He was referring to the movement of the awnings... At that point, no longer knowing if I could move to the right or left on the boat, I asked him if I could take glasses and what he told me yes and then if I could connect the BT to the stereo, but there he replied "use the flip 4 (Editor's note: 10/15w)! I manage the radio....understood? "After a while I see that he plugs in his phone and plays music almost only to his liking. A few hours pass and, with the music now off, I ask him if I could connect my phone or if he feared he had a virus for his stereo. With difficulty, but concession received, but on Tuesday evening then in port in Marsala he took care to detach the front panel and made the small BT speaker disappear. Who knows, maybe since there are some rules to be respected, he thought we could have done like his friend Fichetto on Wednesday evening when from a chartered Cat51' (so cmq with another type of system and not like Alisea directly owned by Alessandro) I will hear music at full volume in the port of Favignana. I give him a hand when asked for the line at the buoy. I try to put him more at ease by talking to him and making him talk about his boat, management etc., giving him advice within the limits of my knowledge mostly in administrative / accounting matters, but nothing ... At one point I managed to think that maybe he got angry because I also turned to his partner sometimes with the intention of doing English practice. In essence, the following days awning and headlamp always up at all hours of the day and night. Tender always on top with no possibility for S and G to breathe because the porthole was right above and for everyone to lie down (everyone in the cockpit to die of heat and piled up. Sails never up. Only Favignana (the flat-rate diesel was evidently fine as it was, because he was paying for the girl's holiday perhaps). Natural cataclysms that have never occurred so Marettimo off limits (in 2017 I had seen TT and 3 with stops in Zingaro, Scopello, LoCapo...). When I apologize to him on Wednesday, maybe we can pull up the tender with the rope, perhaps vertically, so we can let S and G breathe and we can lie down. Answer: "NO, let's just make sure they can open the porthole! The tender is like this!" Moreover, he was about to pull the sheet to lift it, without realizing that his somewhat obsessive mania for control and safety of his boat, his main if not only asset, had led him to put an additional safety line between the two side bollards and then pulling him up I told him that he would do damage. At that point he allowed me to remove the rope, but in the evening then in the port of Favignana he made me disembark with the intervention of the Carabinieri, perhaps also because, when ordered to wash the dishes, I replied that maybe his partner could do it too, who had been quiet and blissful for 4 days without doing much.

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