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.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Yacht sailing holidays & skippered tours in the Aeolian Islands
Super holiday between nature, food, relaxation and fun in a fantastic place like the Aeolian Islands. Matteo transmitted to us his passion for the sea and for the sailboat also making us actively participate in the maneuvers with the necessary indications and instructions. He also complied with our requests (weather permitting) and was also available in the kitchen to prepare excellent tasty dishes. What can I say... Enjoy
For being my first sailing experience it was definitely one of the most beautiful trips made in my life! Many times we look for emotions of this type abroad but the Aeolian Islands have been a perfect setting ... Nicola is a skipper of great experience and attentive to all the needs of his "passengers"... his boat MOONINJUNE is his home and made me feel immediately as if I was at home too! He took us to sleep in anchor in very suggestive places and allowed us to sail every day to the best of the possibilities that the weather offered us! It created a nice atmosphere of conviviality with the other participants and we could learn many things nothing sailboat. Highly recommended experience for those who love the sea, has the ability to understand that you can abandon the comforts of everyday life to fully enjoy what the sailboat can offer!
Surely I will gladly return to sail with Nicola
Fulvio is a skipper of great experience, with a great personality and humanity. The holiday in the Aeolian Islands was wonderful, a perfect mix of sailing and relaxation, in a setting of incredible places. Fulvio shared the choices of stages or things to do with the group, except of course to make decisions due to weather conditions or the final itinerary. In our group we were all strangers, he was very good at putting everyone at ease, at harmonizing the group and at smoothing out any differences. His catamaran is very comfortable, with 4 double cabins with private bathroom, a very spacious kitchen and dinette and cockpit with large table on which to eat.
I definitely recommend a holiday of this type and I will be happy to repeat the experience on Fulvio's catamaran.
Beautiful holiday in the Aeolian Islands and very good skipper Dario, with a great passion for the sea that transmits to all the crew.
Boat kept very well, with order and cleanliness. Only flaw: a week of vacation passes too quickly!
Week in the Aeolian Islands
Nicola Carlo and Diana great people
Incredibly helpful and nice and attentive
The kitchen on board you never want to get off, the service so attentive that you almost don't remember how to open a door anymore..
Fascinating boat as only the gulet can be
Spacious and comfortable
Highly recommended!
Beautiful week in the Aeolian Islands on a boat with large spaces and equipped with all the necessary comforts. Angelo is a very competent skipper and extremely attentive to aspects related to safety at sea. In a week that could have been meteorologically complicated we always felt safe thanks to the accuracy of its forecasts and moorings. Very attentive to the different needs of the crew also has a humanity and a natural sympathy that put you at ease right away, making you feel at home. It is likely that the inhabitants of the sea have perceived the positive energy that was breathed on board: never seen so many dolphins in our lives! Thank you Angelo for the wonderful experience, a big hug to "Lollipop and Lalla" and we hope to see you again soon. Meanwhile... Good wind! Gabriele and Maila
After a night of crossing in complete tranquility and safety, accompanied by the stars, even shooting! (but, of desires, at the time, there were very few ... after all, on the boat, in good company and in the middle of the sea, what more could you want?) we arrived in front of the powerful Iddu, also known as Stromboli. From here, the beauty of the Aeolian Islands has done its good job, among landscapes, bays, water, food, wine and much more. In short, an itinerary that I recommend to anyone!
As always, found very well with the crew and skippers, who are reconfirmed in their availability, professionalism and beautiful company (and also courage!). ??????????
The fun and emotions always assured!!!
With a group of 6 friends we spent a week with Francesco at the Aeolian Islands and we had a great time, the boat is spacious and well maintained. Francesco proved to be an expert in every situation, and despite some storms that chased us, we always felt calm. Nice and accommodating to the needs of the whole crew, he knew the area well and took us to the most beautiful places in the Aeolian Islands! Thanks Francesco!
Giovanni is not a skipper... is the skipper! Man of the sea, with great experience of navigation, but above all a calm, attentive, nice and helpful person. It immediately puts you at ease in its beautiful boat equipped with all the comforts, where you do not feel like a guest but a member of the crew. The Aeolian Islands give great emotions and Giovanni amplifies them, always chooses the best itinerary based on the weather and sea conditions to make you discover corners of paradise and to make you live an unforgettable holiday.
Superb experience, the mini cruise was fabulous.
Antonio always caring, flexibility +++ in the program.
And I think one of the most beautiful sunsets of my life.
I recommend +++
Thank you very much.
The memories from the week spent with Gabriella and Nicola on their boat will stay with us forever! Gabriella is not only a skillful skipper but also a mum who knows how to engage and (when necessary) keep in check children of all ages.
Nicola was a great companion for our 2 children, they had great fun together on the boat and on shore! The played board games, snorkelled, dived and fished together. It was beautiful to witness.
The places Gabriella suggested for us to visit were spectacular and she always recommended things to do based on our interests and moods. The entire week was planned together with great flexibility on Gabriella's part.
We wouldn't hesitate to recommend Gabrilella and Nicola if you are looking for a truly unique experience!
Grazie Gabriella e Nicola!
ELISA? Fantastic! He gave us an unforgettable week in the Aeolian Islands. Kind, helpful and, above all, patient he accepted all our requests. We were guided by her and her experience. So young and so good. It was the putty of the group. A "crew" made up of (former) strangers who, thanks to her, managed to bond immediately. It was the perfect knot for a perfect holiday. Elisa, thanks to the undisputed beauty of the Aeolian archipelago, gave us postcard sunsets like that of Filicudi. He carefully chose the coves with crystal clear water to bathe and relax. But you know, the sea makes you hungry and even in that case Elisa managed to surprise us. Not only with advice on what to eat on board but also on land. I already have the magone. I would immediately leave the moorings to sail again. With her and her catamaran.
It was a magical holiday, out of time and out of the world!!
I loved going full sails!
Captain Maurizio was wonderful, he taught us so many things about sailing!
Diomedes I already miss you!!
Season still cold but when you need a holiday you go ...
The weather was not on our side but the attentive and professional reliable crew made these cold days of March a beautiful experience.
Mario precise and available to our many requests. The boat is spacious, well equipped and well maintained in its interior.... with the new sails it will be super!
We thank Massimo and Giovanni, for making us feel at home and guiding us on this journey that was more than a holiday.
The good company and the enchanting locations have made this sailing an experience full of emotions and memories that will remain indelible over the years.
Ps.
Bonus point: Giovanni's playlists!!
A week FLOWN and SAILED, enjoyed at all times between enchanting places, in good company, entrusted to the experience of Alberto who as a good sea wolf does not speak much but is attentive to the needs of all and, being able to fulfill the requests that are made to him. Prepared, he made us feel comfortable right away. personally I requested some shore excursions and they were made, satisfied and ready for a new experience as soon as possible!
Unique and relaxing experience. Beautiful places, cozy boat and two skilled and helpful sailors, able to meet the needs of the group. You can't ask for anything better.
Unforgettable holiday among the most beautiful places of the southern Tyrrhenian Sea: Amalfi Coast, Cilento and Aeolian Islands. The boat is very comfortable and welcoming, equipped with every comfort and able to offer all the safety necessary for navigation in every wind. Renato, skipper of great experience, always chooses the best of every anchorage in the bay or port to allow you to swim alternating visits on land. Unforgettable in our route the view of Stromboli in night navigation. Luciana is an exceptional cook who made us discover the delight of a plate of freshly caught shrimp or tuna.
This was my first sailing experience and I couldn't have asked for better. Giampaolo is a very prepared skipper who loves the sea and his work and made us visit some beautiful places. Comfortable and clean boat and great company. Absolutely to be repeated!
As a first experience we could not find better . Sailor expert of the places both at sea and on land, we visited glimpses of the enchanting Aeolian Islands.
Sailing alongside dolphins was an almost mystical experience. Skipper prepared, attentive to the needs of the board, all safely even when the waves are felt.
It was not a holiday but an unforgettable adventure.
A fantastic crew! We had a great time both with the
Skipper that with the other guys, of course the spaces are what they are, but you adapt! An unforgettable experience both for the landscapes and for the friendships born, I recommend to everyone!
Nicola is a professional and a successful business man. We delayed our flight and found the solution so that no one would be harmed. Raffaelle his assistant was always looking out for us.
7 reasons to choose the Aeolian Islands for your next sailing holidays:
A consistent climate and constant winds allows for good sailing from April to October.
A different island for each day of the week are to discovered with your new friends.
The amazing Stromboli, and its gushes of fire - as well as Vulcano, that can be climbed.
Experience the social evenings of Panarea, unwind in a bar overlooking the sea and villas.
Revisit the iconic locations from the film "Il Postino", and dive into the blue of Cala Pollara in Salina.
Dive into the depths of Filicudi and Alicudi to discover the wrecks, widely seen as one of the best places to dive in Italy.
Taste real delicacies, such as cunzato bread, "condito", accompanied by a glass of Malvasia, as well as the inevitable Sicilian sweets such fresh cannoli.
The best destinations to visit during your sailing holidays in the Aeolian Islands:
The Aeolian Islands are a great option for all lovers of sailing and the sea. This splendid volcanic archipelago owes its name to the god of the wind, Aeolus, who is believed to have ruled here, together with Vulcan, the god of fire. Elements that have forged a truly unique landscape - with cliffs overlooking the sea, headlands and rocks ranging in colour from the white of pumice to the dark red of basalt, and the gold of sulfur.
Lipari and Salina
Lipari is commonly the departure point for sailing holidays in the Aeolian Islands. Of the seven islands of the archipelago, it is the largest and most densely populated, with around 10,000 inhabitants. As for the sea and the beaches to be reached by sailboat, you will be spoilt for choice - Pietra Liscia, Acquacalda, Papesca, Porticello, Valle Muria, Vinci and more are each worth visiting. Salina is nicknamed "the green", and for its tranquility it has become a favourite for families with children - this is the island that has fascinated Massimo Troisi, a destination then chosen for the film "Il Postino", the island is also famous for its capers and Malvasia wine, considered the nectar of the gods. An obligatory stop is the legendary Alfredo, from there you can taste real delicacies, such as the cunzato bread and the typical Sicilian granita.
Stromboli and Vulcano
Stromboli and Vulcano are the two islands with volcanic activity still present. In Stromboli, when the sun goes down you can see the flames of the volcano zampillillare, in a show that is unique to the world. It is also worth sailing under the Sciara del Fuoco, a slope of ash and lava that descends from Stromboli to the sea. Then there is the village of Ginostra, which is also very beautiful - reachable by sea on a sailing boat, and a place that you can only move with mules, and more recently electric “trolleys”. Vulcano is a very popular island, especially for the spa and the famous climb to the great crater of Vulcano.
Panarea
Panarea is the smallest island, and one that at the same time is the most popular among the exclusive type of traveller. One of the most famous beaches, Punta Milazzese, is nearby to a charming prehistoric village, that sits southwest of the pier of San Pietro. Another cove where you can moor for a dip is "Junco", this small cove is home to pools of water surrounded by a range of cliffs. Finally, the islets of Basiluzzo and Lisca Bianca sit just a short sail away.
Alicudi and Filicudi
To the west of the archipelago, closer to Palermo, Alicudi and Filicudi are for lovers of nature and tranquility. Alicudi is the wildest of the two islands, there are no vehicles, and there is a wild and unspoiled landscape, ideal for a perfect mix of Sicilian seaside holidays and hiking. Filicudi is protected from the winds and is an ideal location for diving. Both islands are home to extraordinary beauty and are a great anti-stress refuges for those who want to relax and enjoy unique landscapes of the world.
Tips to help you to better plan for your next sailing holidays in the Aeolian Islands:
All you need to know about your next cruise in the Aeolian Islands aboard a sailboat.
The best time for a sailing holiday in Italy
The climate is temperate all year round and the constant winds allow you to sail smoothly from April to October. Summers are not hot because they are mitigated by the sea breeze and in spring, the vegetation surrounding the fertile islands is an explosion of colors and scents. Even out of season the weather conditions are favourable with pleasant temperatures that entice to a nice dip. Between relaxation, nature, and fun, the Aeolian Islands are ideal, both for families and groups of friends. Young and old are fascinated by the volcanic landscapes. Young adults can find the right mix of adventure and fun, alternating long days at sea with lively evenings.
Pricing of sailing holidays in the Balearic Islands
The archipelago is the destination of many smaller sailing trips. By catamaran, sailing boat, or flotilla you can find a solution that best suits your needs. Whether it's individual boarding or whole boat reservation, there are proposals from €400 per person for a week with skipper.
Transport options to and from your holiday
The Aeolian Islands do not have an island airport; the nearest ones are Reggio Calabria, Catania and Palermo. The recommended port of embarkment is Milazzo although there are transport options from Reggio Calabria, Messina, Palermo, and Naples.
Sailing holidays in the Aeolian Islands - why you should travel with a local skipper
If you want to fully enjoy your sailing holiday in the Aeolian Islands in the best conditions, we recommend that you go choose a trip with a local skipper. Travelling with a skipper who has insider knowledge on the area, allows travellers to fully immerse in the pleasure and relaxation of the holiday. Where individuals on the trip wish to learn or practice their sailing skills, skippers will be there to integrate travellers into the responsibilities onboard.
