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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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4.5

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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4.5

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

5 departures available

September - 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

4 departures available

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

3 departures available

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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Aeolian Week

Italy: Aeolian Islands

7 days - 6 nights

One departure available

September

€750

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€730

€657

Per person

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

2221 reviews

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

08/29/2026

Mattia F.

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IT

The holiday overall was fun, especially thanks to the group I was on the boat with, with whom I got along very well. However, from the point of view of the organization of the flotilla, there are several aspects that in my opinion should be improved. A lot of time was lost from check-in and I had the feeling that some situations were not handled in a particularly coordinated way. Even the first dinner, proposed at € 25, did not seem adequate to the price paid: probably, knowing in advance exactly what would be offered and at what price, we would not have accepted it. The skippers were good and helpful, but I found little involvement in really creating a flotilla dynamic. During the day the boats spent a lot of time sailing separately and there were few opportunities to get together and get to know each other. Even in the evening, very few events or common moments were organized for the whole flotilla. Personally I would have preferred to do many more packages/stars during the day and evenings together and, above all, get to know the people of the other boats more. Even some of the most beautiful coves, such as those of the Faraglioni di Lipari, in my opinion have not been exploited well: in some places we have stayed too little time, giving again the feeling of a non-optimal management of time and travel. Another aspect that I found particularly problematic concerns the issue of the licenses of some skippers. I was told that some did not have the necessary license to play the role of skipper towards people they did not know. I find this situation not very reassuring, especially considering that the holiday had been paid regularly and in full. The fact that, in the event of a possible check, there was even the need to provide an untruthful version of the facts to the Guardia di Finanza is, in my opinion, something to be absolutely avoided and clarified before departure. The number of people per boat also seemed excessive to me. We were 13 people on a sailboat, a number that I found uncomfortable and which, from what I had read in the description of the holiday, did not correspond to what I expected. In addition, skipper and co-skipper slept in the saloon and the additional berth was in fact sold, despite it being a space that I found practically unlivable. On a holiday of this type, comfort on board should be considered a fundamental aspect. Ultimately, I had fun and I take home a good memory especially thanks to the people I shared the boat with. However, precisely because the flotilla format seemed very interesting to me, I expected greater organization and above all greater involvement between the different boats. In my opinion there is a lot of potential and you can improve a lot with a little effort from Different Sailing. I understand that managing a large flotilla is not easy: 10 boats and about 120 people are really a lot. Precisely for this reason, however, I believe that even more accurate planning and coordination are needed, in order to really create the flotilla spirit and not find ourselves, for most of the day, with each boat proceeding on its own.

A week in the Aeolian Islands - 6 islands in seven days

08/28/2026

Tiziana D.

"And you haven't seen anything yet..!" Our captain kept telling us. And so it was, in a crescendo of wonder and amazement: the long baths in ever-changing coves, the wait for the sciara and the wonder of the rain of drops of fire, the romantic sunsets every evening more spectacular, the warm nights under the shooting stars and the magic of the silent sunrises, the sailing in the safety of the port so as not to be reached by the incoming storm (we sleep with the air conditioning .. daje!!), the dancing aperitifs, the iridescent colors of the rocks, Bennato, Dalla and Queen in the background, the unbeatable dishes of the Bitta di Maria, the pane cunzato and the almond granita, the breathtaking beauty of Filicudi, the deep seabed in search of fish (look: two tuna, no they are amberjacks!!), the final surprise of the dolphins on the last day and the caves of ammmore ("so you just don't leave each other anymore!"). Thanks to [hidden] and Nicola, a brave but prudent captain, who pampered us all together with Ilaria and gave us unforgettable memories. Simone and Tiziana

Unforgettable adventure in the Aeolian Islands

08/28/2026

Massimo P.

Boat [hidden] - Aeolian Islands - 15/22 August 2026 "UNFORGETTABLE BAD EXPERIENCE" Writing a review is not an indication of malice or defamation. What I am writing is exclusively a personal opinion based on the facts and the experience actually lived by me and my crew on board from 15 to 22 August 2026. *1. Skipper change and language barrier* About 24 hours before the departure we were informed by Sailsquare of the change of skipper. Shortly after, with some guests already on the road, the owner informed us that the new captain did not speak Italian, but only English. This condition created immediate discomfort, considering that several members of the group do not speak English at all or do not master it. However, less than 24 hours before the set sail and with all the participants already on the road or about to leave, it was in fact impossible for us to cancel the reservation. In practice, this language barrier has generated continuous misunderstandings and critical slowdowns for us during the fast maneuvers of mooring and docking, and has made it extremely difficult to collaborate to manage technical failures that have occurred on board. The skipper's instructions had to be continuously translated and reported to the other members of the group, creating constant word of mouth and making communications less immediate in a context where impact communication is essential. Precise with intellectual honesty: the replacement skipper was an exquisite person who made real efforts to safely steer the boat. *2. Check-in conditions* At check-in on 15/08 at 12:00 we found: interiors that in our opinion were not clean and sanitized, standard fridge with mold and smelly not usable for us, portable makeshift fridge on board not working for us due to lack of energy autonomy, only one stove out of two working, cutlery and other accessories with widespread rust. *3. Electrical failure and autonomy* First night at anchor in Filicudi total electrical blackout, without anchor lights and without lighting on board. We had to use our personal flashlights to signal our presence to an approaching catamaran avoiding a collision. In the following days, it was necessary to intervene several technicians in different ports, including Salina. We were told that the alternator was faulty and part of the photovoltaic wiring was worn. The installed spare part has proved to be defective. For about 7 days we had very limited energy autonomy. The toilets could not be used as the drain was electric, they gave off nauseating smells and had continuous and unacceptable episodes of excrement rising making the boat unlivable. Not to mention the deterioration and consequent loss of various food supplies, the engine of the Tender is not working etc.... Most of the time we spent in the ports solving problems with the boat and waiting for technicians to do it. All of the above corresponds to facts that we have experienced firsthand. After a year of work, all this is unacceptable !! The only luck was the group: we were very united, everyone gave 101%, we were sailors, mechanics and psychologists for each other. Without this extraordinary cohesion and mutual support, we would never have been able to complete this experience. *Personal opinion:* From my personal experience from 15 to 22 August 2026, I would never, ever book it again and I would not recommend it. 0 stars for the boat 0 stars for the owner.

Wonderful Aeolian Islands on a 15 mt sailing boat - Cabins with private bathroom

08/28/2026

Francesco M.

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IT

I scroll through the slides of memories of this wonderful week of sea and relaxation together and I see the sunrise in the peace of Alicudi, the dolphins sailing, the sunset from the cliff in Filicudi and the pizza on the walls, the narrow streets of Salina and the bread cunzato by Alfredo, the cheerful night of Panarea, the red of Stromboli in the dark of the evening and the dinner with fresh tuna, laughter with fellow travelers in the center of Lipari... And the chats with a glass of wine in hand, the kindness in Ciccio's eyes, the friendships born and the sadness of the last goodbye on the pier come to mind. But I have strong memories of Angelo, a skipper with undoubted experience, a passionate cook, a kind leader, a wise guide with whom we promised to see each other again for another sail. Happy sea [hidden]!

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