Why you should book a holiday with Sailsquare?
The leading sailing holiday marketplace
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 Islands1341 reviews
Would you like some support using the platform? We've (almost) always got the answers!
Can't find the perfect holiday for you?
Use our free holiday concierge tool - and let us find your dream sailing experience for you!Let's find it together!
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 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.