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Yacht sailing holidays & skippered tours in the Aeolian Islands

A holiday in the Aeolian Islands: Vulcano, Lipari, Salina, Panarea, Stromboli, Alicudi, and Filicudi - seven volcanic islands to be discovered by sailboat. A unique experience in which you will navigate between craters, geysers, volcanic rock rivers.

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4.9

Aeolian Islands on a luxury sailing boat

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€700

Per person

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4.9

Aeolian Islands in a big and new catamaran: sea, sun, relaxation

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€980

Per person

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4.5

Enjoy the Aeolian Islands with skipper and hostess

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

€1,039

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

August - October

Starting from

€680

Per person

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4.5

Sailing holiday with maximum comfort

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€700

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

August - October

Starting from

€607

Per person

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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4.7

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August - September

€750

€638

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

5 departures available

August - September

Starting from

€723

€650

Per person

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5.0

Aeolian Islands on a sailing boat: a tailor-made holiday with an exclusive boat

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September

€800

Per person

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4.7

Aeolian Islands: well-being, taste and fun

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€690

Per person - min 2 pax

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4.9

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€800

Per person

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Reviews - Yacht sailing holidays & skippered tours in the Aeolian Islands

2206 reviews

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/26/2026

Marco C.

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IT

Really fantastic experience in the Aeolian Islands! 🌊⛵ A sailing trip that I will definitely take with me: the skippers were simply fabulous, professional, helpful and able to create a pleasant and engaging atmosphere right from the start. They made the experience even more special, making us experience the sea and the islands in the best way. The boat is very spacious, comfortable and well organized, perfect for sharing a week with 10 or 11 people, for 13 maybe it is a bit cramped. The only small flaw concerns the cabins, which are quite hot, especially at night. A different arrangement or position of some portholes could probably be considered, so as to better facilitate air exchange and make the rooms more comfortable. For the rest, an experience absolutely recommended! The Aeolian Islands seen from the boat have a completely different charm and, thanks also to the skippers and the group, it was a holiday made of sea, laughter, emotions and beautiful memories.

Aeolian Islands: between sea and authentic flavours

08/26/2026

Luisella C.

Spacious and comfortable boat with Skipper Carlo: professional and helpful, a real treasure; It is impossible to forget the calamarata of freshly caught squid that he cooked for the guests. An experience definitely to be repeated.
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Unforgettable adventure in the Aeolian Islands

08/25/2026

Antonella C.

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IT

I would like to point out right away that this is not my first experience on a sailing boat; I know perfectly well the dynamics of navigation and sea life, and for this reason I am able to distinguish a small occasional inconvenience from a serious and unacceptable lack of maintenance and safety. I waited for my return from vacation from 15 to 22 August 2026 before reviewing, but the facts are all documented and verifiable. The boat is in a state of chronic degradation and neglect that the owners knew very well, as the previous reviews on the site clearly demonstrate. It was not at all unexpected, but a completely unsuitable means of navigation. Less than 24 hours before departure we were notified of the change of skipper. The owner had known for some time that he could not drive the boat (since he was also not present the previous week and had been replaced) but he warned with all the guests already traveling to Palermo, effectively putting us in front of the fait accompli: the substitute spoke only English. In addition to the seriousness of replacing the agreed Italian skipper, when we pointed out the problem the owner unloaded the responsibility on us, saying that he had taken it for granted that young guys like us knew English and that it was inconceivable for him that we did not speak it. The language barrier has slowed down maneuvers and communications both in emergency situations and towards mechanics. However, I would like to point out that the replacement skipper was an exquisite, professional person with infinite patience, who worked miracles to safely drive a vehicle in hallucinatory conditions. The reality on board was a hygienic and logistical nightmare. Embarked at 12:00 at the request of the owner to ensure impeccable cleanliness, we found the boat dirty, the standard fridge unusable and infested with mold, rusty fires (working 1 out of 2) and cutlery covered in rust (replaced by the property only at the end of the holiday, demonstrating the disinterest in those on board). The toilets gave off nauseating smells and, despite the fact that we held down the drain for a long time as instructed, the rise of feces was constant for days. From a technical and safety point of view, the first night in Filicudi we were completely in the dark due to an electrical failure, risking a collision with a catamaran that, not seeing us, was coming directly at us. Although the owner had provided us with an emergency LED, this had not been positioned by the skipper or was unloaded: the fact is that it was us guests, with our personal torches, who had to wave our arms to signal the presence and foil the accident. An emergency task that was not up to us in the slightest. Following the blackout, the skipper was even forced to weigh anchor with his bare hands in the dark. The intervention of the mechanic in Salina confirmed the truth: the failed alternator burned the batteries and the cables of the photovoltaic panels were rotten, deformed and burned by time. A pre-existing degradation that has never been maintained. With the replacement alternator also proving to be defective and the photovoltaic connections never repaired, we were left for the whole week with an extremely limited amount of energy, forced to continuous and absurd sacrifices: we literally had to choose from time to time whether to turn on the lights or power the portable refrigerator, or whether to flush the toilets or take a shower. This caused food spoilage, the inability to cool the water to 40 C and continuous inconvenience to personal care. Added to this was the bridge cluttered with scattered ropes at constant risk of injury and the shameful conditions of the port of departure and return to Porticello (Santa Flavia). A mere port of call for fishing boats completely devoid of drinking water, electricity, services and sanitation. We were docked at the pier in very bad sanitary conditions, squeezed between rotten, broken and abandoned fishing boats, with stray cats jumping everywhere. Situation culminated on the last night with the presence of cockroaches on board. The owner's behavior was unacceptable: he constantly avoided taking responsibility, minimizing any problems. Only after my partner called him following my crying fit, making him realize the real seriousness of the situation we were in, he sent an apology message in the whatsapp group. A purely formal gesture, given that he continued to minimize the incident and not take responsibility, focusing on his promptness in calling a mechanic and having the alternator replaced, but this did not solve the situation of great discomfort that was on board. A nightmare holiday. Dangerous boat and completely unacceptable management. P.s. The vote for the Skipper is for Gaetano and not for Vladimir who replaced him.

Unforgettable adventure in the Aeolian Islands

08/25/2026

Cristina D.

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IT

Extremely bad experience – boat and owner management absolutely to be avoided Our experience on this boat during the holiday in the Aeolian Islands from 15 to 22 August 2026 was extremely negative and, based on what we have experienced, I do not recommend either this boat or the owner's management. Unforeseen events during a boating holiday can certainly happen. The problem, however, is how they are managed. In our case we encountered a series of technical, maintenance and organizational problems that significantly compromised the quality of the holiday. We suffered a serious failure in the electrical system: a problem with the alternator caused damage to a battery, leaving us without electricity for a period and, subsequently, with an extremely limited availability of energy. The consequences were heavy: refrigerator not working, difficulty or impossibility of using the bathrooms and related electrical drains, shower, lighting, phone charging, windlass and other on-board utilities. The situation was not resolved with a simple intervention: in the following days several mechanics intervened, at different times, in an attempt to restore the operation of the boat. It was also necessary to resort to a power station to be able to keep some essential services active. We also had problems with the photovoltaic system, initially believing that the latter were due to battery failure. Subsequently, however, the technicians who intervened on board found cables and connections of the photovoltaic system seriously deteriorated and burned. As far as we were told during the interventions, their state appeared to be attributable to a pre-existing deterioration and not simply to the failure that occurred during the holiday. This has contributed to making it very difficult to maintain the boat's energy autonomy. Added to this was the change of skipper communicated only two days before departure. The new skipper spoke only English and created considerable communication difficulties within the group, especially during maneuvers and when we had to manage breakdowns and communicate with the mechanics on board. Among the aspects that affected us negatively was also the equipment of the kitchen: upon our arrival we found cutlery and utensils completely rusty and not suitable for use. The problem was not solved during our stay: only at the end of the holiday, after our specific report, the owner proceeded to replace the utensils and cutlery. In fact, the replacement took place when our holiday was over. Finding rusty utensils intended for the use of guests raises serious doubts about the attention paid to checking the condition of the boat and its equipment between bookings. I am talking about problems that, as a whole, have concretely affected livability, hygiene, functionality and the quality of the experience. What left me most disappointed was the behavior of the owner. Faced with the numerous problems that emerged, I had the clear impression several times that his main objective was to minimize his responsibilities and find a justification for the problems, rather than listening to the guests and trying to minimize the inconvenience. Unforeseen events can happen but As far as I am concerned, this experience has left a deep disappointment. I would not choose this boat again and I would not recommend it to other Sailsquare users. My considerations are based exclusively on personal experience during the holiday and are supported by photographs and documentation of the interventions carried out on board.

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