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Crewed yacht sailing holidays & tours in the Aeolian Islands

Get on board on a crewed sailing holiday in Corse for the most relaxed time ever.

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Get onboard solo, with your family or your friends

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 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

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 - Crewed yacht sailing holidays & tours in the Aeolian Islands

167 reviews

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Discovering the Aeolian Islands by catamaran with hostess

08/29/2025

Alessandro D.

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Italy

Unfortunately the organization of the catamaran was absolutely not up to the wonderful place that are the Aeolian Islands: - Daniele, the reference of the holiday on the booking page, not received like anyone else from the organization, except Valentina who was not of great help when we needed it; - All the equipment of the catamaran, which we paid for and had to be included in the experience, was not present. Snorkeling gear, fishing gear, BBQ, drone, water toys, and Wi-Fi were not there. They replied that after washing the boat they didn't remember to put them back on board (it seems rather unlikely to me as an excuse). And in any case, no one has deigned to apologize or consider a partial refund even as a gesture; - the bathrooms of the catamaran, in 2 cabins, never worked properly from the first moment and were clogged 3 times (obviously we know boats and we know that you should not throw anything into the toilets, and these were malfunctioning from the beginning); - in check-in and check-out we needed a trolley to transport the luggage of the whole crew to the port and obviously no one from the organization provided us with any trolley, nor did they reveal themselves; The only really positive note: skipper Gianluca and his wife Ylenia. Gianluca is an exceptional captain who has been able to solve all problems from the beginning of the holiday to the end, always sailing safely but also showing himself very willing to take us with the tender to the various coves of each island. Ylenia cooked divinely and was always kind and super helpful. In summary, the Aeolian Islands are a beautiful place to explore by boat/catamaran, but we absolutely do not recommend relying on this organization/company that has not proven to be even remotely up to expectations.
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Aeolian Islands: wellness, taste, fun with fabulous cook on board

08/26/2025

Valentina S.

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Italy

It was my first experience of a sailing holiday and inexperience played a fundamental role unfortunately. In fact, I chose a lot by feeling, especially looking at the itineraries and letting myself be conditioned by the beauty of the places, I gave little importance to the choice of the boat which is fundamental. [hidden], is a sailboat with all the comforts but unfortunately it has little outdoor space and in 6 guests plus 2 of the crew we could only sit or share a small mattress. The other available outdoor seat was occupied by the tender which was used only to go shopping in Lipari. Another thing that must be considered is the speed of the boat, going at 5 knots per hour we did 3 to 5 hours of navigation a day, very often taking the first swim not before 12, which x a boat holiday is really absurd. The inexperience also played on the price: the cost of the departure holiday is good but does not include anything, the price of the galley is roughly defined on paper between 200 and 300 per guest but in this case we went over the top: between food, marine (even 200 euros x a night), fuel and water I spent 400 euros individually. As for the itinerary I was lucky because it was 1 week of excellent sun and calm sea and I was able to visit all the islands except for a few and filicudi. Wonderful places, beautiful sea but too touristy stops. I thought that going by boat I would see unusual places, accessible only from the sea, with little confusion, instead we often attacked in crowded places and very far from the shore which was like always taking a swim in the high seas. The few times we ventured, we risked drowning or being run over towards the shore because the tender was never used by the skipper. As for the skipperGiacomo and his wife Laura I can say that they are very good hosts, kind and helpful but I don't think they are too experienced and therefore limit themselves to a simple itinerary. Laura is an excellent cook. My luck in addition to the good weather were also the travel companions with whom I bonded immediately even though I did not know them and we spent days full of laughter and fun. In conclusion, it was a good experience for me that I will certainly do again but controlling every single aspect well.
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Fire, sea and land in the Aeolian Islands with hostess

08/26/2025

Manuela M.

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Italy

Unforgettable week! Beautiful places and weather. The islands were one discovery after another, thanks also to the experience of Gianni and Giovanna in taking us to the most beautiful streets in the most spectacular moments (a unique emotion to witness the sciara del fuoco of Stromboli. All the advice on clubs or what not to miss of the islands is also excellent. Life on board has always been a great mediation, inevitable between strangers in such a confined environment, but Gianni and Giovanna have always known how to mediate and always keep us safe. Laughter out loud and endless aperitifs thanks also to a crew that smoothly returned to the kitchen. At my third experience of this kind and with some neophyte travel companions we all managed to have a week of intense vacation following the personal predispositions of everyone, between adventure and relaxation. Personally, the icing on the cake was the final day made of pure sailing, in which we were able to help the navigation and really enjoy the sea! The choice of the port of departure and arrival is really excellent which allows you to be reached easily and without too many changes of means, A big hug to the legendary Captain Gianni and the sweet Giovanna. your "Valentì"
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Discovering the Aeolian Islands by catamaran with hostess

08/24/2025

Francesco M.

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Italy

The experience in general can only be positive. The cruise allowed us to see most of the places we had set ourselves, except, unfortunately, for Stromboli, which became unreachable due to sea and wind conditions as the days went by. The catamaran was a 40 foot (12 m) Lagoon which offered the right spaces for 8 people in my opinion. Of course, with the same crew, the bigger you take it, the more comfortable you are. A bit sore notes concern the organization during the check-in phase which in essence was not conducted with the staff of Sailsquare or other company or trusted staff of the owner able to explain, to us and to the skipper above all, the equipment on board. So much so that the catamaran did not have, compared to the list on the web page of the experience, a Sup, barbecue, snorkeling equipment, fishing equipment and Drone, awning to close the cockpit and other furnishings. All equipment that, if present, would certainly have increased the evaluation of the experience, also by virtue of the costs incurred per person. A special note to skipper Gianluca and hostess Ylenia, simply perfect for the whole trip. They pampered and cared for us in every possible way, as well as the ability to manage weather, moorings and routes to avoid problems. Finally, it should be clarified about the ground contact person who must be the guarantor of the experience and the contract stipulated with us throughout the travel period. However, this experience is recommended.

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