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Different Sailing

Provider type:

Organisation

City:

Roma

Member since:

2016

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1635 Sailsquare travellers have been on board my experiences

Gallery

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20+

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My sailing areas

Aeolian Islands

Italy

Ionian Islands

Greece

Grenadines & Martinique

Caribbean

Pontine Islands

Italy

Northern Sardinia

Italy

My boats

Type

Sailboat

Toilets

3

Cabins

4

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15+

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Travel with peace of mind

Total transparency

Want to avoid surprises? Find out before you book who your skipper and fellow travellers will be. Do you have questions or doubts? Send a message to the skipper!

Flexible cancellation

Cancel within 30 days of departure for any reason and receive a full refund. Want even more? Purchase the extension to cancel your booking until your departure.

Constant support

Our dedicated multilingual support team is always ready to assist you, before and during your holiday, and is always in touch with the skippers we work with.

Reviews

4.5/5

out of

370

reviews

Skipper

Boat

Destination

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

09/9/2026

Giovanna G.

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IT

I must say that everything went very well! First experience in the flotilla and it was super! I recommend to all those who want to have a fun-filled holiday!
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

09/3/2026

Francesca L.

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IT

Overall, I liked the experience, but I would have preferred more attention and care in the organization of travel, group moments and, above all, moments dedicated to the sea. Unfortunately, due to some organizational shortcomings on the part of the Different Sailing staff, I feel that it was not possible to fully enjoy the experience. The boat was also delivered to us late and in less than optimal condition: it was not particularly clean and in the following days we had to take care of the cleaning ourselves. As for the holiday itself, however, it was a lot of fun, especially thanks to our crew, made up of wonderful people who helped make the experience much better. However, it should also be noted that, initially, a maximum of 10 people per boat was expected, while in the end we found ourselves in 13, without having been adequately informed of the change. In my opinion, 13 people were a bit too many for the available space and this inevitably affected the comfort on board. Ultimately, I can't say that the experience was totally negative, because the group and the people I met made the holiday enjoyable. However, considering the organizational aspects and the condition of the boat, we will probably choose another company rather than Different Sailing in the future.

Different flotilla in Ionian Greece: nature, new friends and fun

09/1/2026

Davide D.

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IT

Overall nice experience, but mainly due to the people who participated and the beauty of the places visited. From a human point of view, my skipper and co-skipper are two wonderful and super pleasant people. The organization should be reviewed on some things and there is certainly room for improvement: - in 7 days practically no boat has almost never sailed (I can understand that the wind cannot be controlled, but even when there is sufficient minimum it has not even opened the sails a little just enough to let the crew enjoy the experience, but the impression of many was that there was no desire to unfurl the sails because it was more convenient to travel by motor); - lack of clarity on the program to follow (very often improvised); - confusion about the galley (practically all the boats received an expense that did not fully correspond to the agreed list. If it had been the crew's task to verify, we were not told, perhaps we could have at least pointed out to pay attention since many were at their first experience); - insufficient moments of celebration and socialization (few times we packed with the boats, most of the time they were all "mismatched" and even when the music was played, maybe just 2 evenings, it was turned off quite early. Many of us did not feel the typical spirit of the flotilla); - selection of the crew (some elements proved to be disturbing even before the start, already when booking the holiday, and it was the common idea of many crew members that these elements should not have had the opportunity to participate); - little involvement from the skippers and co-skippers (there was no initial presentation of the various components and between the various crews, which normally happens in other holidays of the same type, but even throughout the holiday it was noticed that they were doing a lot of their business; - inadequate explanation of the main safety rules (we have been extensively explained how to use the toilet, how to arrange personal and galley things, but not what to do or not to do on the boat for our safety and that of others).
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/31/2026

Ignazio F.

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IT

Well organized holiday, congratulations to all the staff who were able to manage any need in the best possible way, taking care of every aspect, from fun to safety.

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