Sailing trip Sicily & Lipari Islands
Sailing Trip Sicily & Lipari Islands
Active volcanic islands, historic coastal towns and deep blue sea: The Lipari Islands are among the most fascinating sailing areas in the Mediterranean. With Sailing-Classics, you discover Sicily and the Aeolian archipelago between Palermo, Syracuse, Lipari, Vulcano and Stromboli – intense, varied and full of Mediterranean atmosphere.
Our sailing trips start depending on the route in Palermo or Syracuse and lead to the most beautiful islands of the Aeolian archipelago north of Sicily. In addition to classic 7-night trips, we also offer longer journeys with 10 nights, allowing additional stops and more time for island explorations. Between volcanic landscapes, small harbour towns and black sand beaches, you experience an extraordinary mix of nature, culture and genuine sailing feeling.
Quick facts about sailing trips around Sicily & the Lipari Islands
Highlights
- Volcanic islands with unique landscapes and Mediterranean flair
- Night sail at active Stromboli & hike on Vulcano
- Combination of sailing experience, nature and Italian culture
The best travel time
The region around Sicily offers mostly pleasant to lively sailing conditions with thermal winds and open stages between the islands. Especially around Stromboli and along the northern coast of Sicily, an intense sailing experience arises with impressive landscapes and wide horizons.
Sailing conditions
The best time for a sailing trip around Sicily and the Lipari Islands is from May to October.
In spring and early summer, the area shows itself pleasantly calm and green, while the summer months impress with warm water, long evenings and stable conditions. Autumn also offers ideal temperatures and a relaxed atmosphere.
Arrival
Arrival is via the airports Palermo (PMO) or Catania (CTA), depending on the route.
From there, you can conveniently reach the boarding ports in Palermo or Syracuse by taxi or organised transfer.
Top highlights around Sicily & the Lipari Islands
Lipari – lively island with Mediterranean character
Lipari is the largest and at the same time liveliest island of the archipelago. Narrow streets, cosy cafés, white houses and a relaxed harbour promenade give the island its typical Mediterranean character. At the same time, the surrounding bays offer crystal-clear water and ideal conditions for relaxed swimming stops.
The island combines Italian ease with volcanic landscapes and forms a perfect starting point to discover the diversity of the Lipari Islands.
Vulcano – black beaches & hike to the crater
The island of Vulcano impresses with its distinctive volcanic landscape, sulphur springs and black sand beaches. A special experience is the hike up to the crater, from which spectacular views over the island world and the open sea open up.
The contrast of dark lava rock, intense blue water and rising sulphur fumes makes Vulcano one of the most impressive stops on the trip.
Stromboli – nocturnal natural spectacle at the active volcano
The active volcano Stromboli is one of the most spectacular natural experiences in the Mediterranean. Particularly impressive is the passage at night, when small eruptions and glowing lava regularly become visible against the dark sky.
From the water, the island unfolds a unique atmosphere: the open sea, the dark volcanic landscape and the glow of the crater create a moment that many guests consider the highlight of the entire journey.
Taormina & the Sicilian coast – culture and Mediterranean elegance
On trips from or to Syracuse, Taormina is also one of the highlights of the route. The elegant coastal town is spectacularly situated above the sea and fascinates with historic streets, small squares and impressive views over the Sicilian coast.
On the way there, you sail along the east coast of Sicily with a view of the mighty Etna, whose silhouette shapes the landscape and vividly reveals the volcanic history of the region.
Your sailing trip – optimally planned
Would you like to know whether a 7- or 10-night trip suits you better or which route offers the most beautiful island experiences?
Our experts will be happy to advise you personally and help you find the right sailing trip around Sicily and the Lipari Islands.
Mediterranean volcanic landscapes & intense island hopping
A sailing trip around Sicily and the Lipari Islands combines impressive nature with Italian joie de vivre. Between active volcanoes, small harbour towns and open stages, you experience an area full of contrasts and special moments.
Whether during a swimming stop in turquoise bays, dinner on deck or the night passage at Stromboli – every stage offers new impressions and an extraordinary atmosphere between fire, sea and Mediterranean ease.
What our guests say about their time on board
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Introductory Sailing Trip in Malta
Ahoy, we'd love to come back.
On that morning of the third day, the waves were high and lashed with great force against the hull of the majestic Chronos. When I asked what wind force we were experiencing, Felix, the young and passionate captain, replied, “We’re at a 5.” It was a surreal scene: a constant up-and-down motion, clinging to any part that resembled a handhold, and the hot coffee, sitting steady on the breakfast table (thanks to the rubber mat).
Read the full review
My partner and I spent three unforgettable days on the Chronos, filled with many such experiences. Although I'm naturally a bit of a worrier and have a deep respect for the vast ocean, we felt safe and comfortable the entire time. Not least because of the professional crew, who were very helpful, patient, and went out of their way to pamper the guests. We were also enchanted by the culinary journey aboard the ship, with its many delicacies. How the cook—always with a touch of humor on his lips, even in such cramped quarters—managed to cater to these 20 guests remains one of the great mysteries of seafaring.
You can look forward to a little adventure—whether it’s relaxing in the sun on deck, taking trips by motorboat to the most beautiful spots, watching the captain at work, or helping to hoist the big sails; a journey you won’t experience every day.
Ahoy, we'd love to come back.Samuel and Elke on the Chronos, sailing around Malta in June '26 -
We enjoy our 5th trip
High praise
This is the fifth time we have enjoyed a trip with Sailing Classics, this time between the Greek islands. And in November we want to sail across the Atlantic with the Rhea. In Pieter we have met an outstanding captain who has given us a lot of pleasure. I would also like to praise the speaker Marc, who introduced us to Greek history with his immense knowledge and his engaging and humorous manner. I would also like to praise the entire team.
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Peter and Lore in October on the RHEA - Sailing & History in the southern CycladesPeter and Lore -
Loved every minute of it
Absolutely marvelous charter
It was an absolutely marvelous charter. Loved every minute of it. I have chartered boats a number of times, and I have never had such a friendly, positive, and accommodating captain and crew. And the food was superb.
Read the full reviewDavid (USA) with family and friends after a private charter of KAIRÓS in Croatia July 2025 -
3 days in Italy
It was marvelous
About 10 days ago, we had zero sailing experience and no idea what to expect as a family with two young kids (ages 5 and 7) boarding a 3-night charter in the south of Italy. As we waited for the tender to bring us aboard, we spotted our fellow passengers - no other children in sight and most well outside our usual age range. We were more than a little nervous.
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But wow - it was marvelous. From the moment we boarded, we felt not only welcomed but truly cared for. Normally, our daughter is quite shy around men, yet she immediately gravitated toward Captain Niko. She followed him around the boat with admiration, and he responded with incredible patience and kindness.
Everyone was fantastic and worked together like a well oiled machine. Thank you for a once-in-a-lifetime experience that we hope becomes a lifelong tradition.Sophie and her family after their trip at the Amalfi coast -
Wedding anniversary on board
A special experience
You are probably more than aware that sailing on the Rhea is a particularly beautiful experience. It was a special experience for me. Not that it was my first time sailing (North Sea, Atlantic, Mediterranean Sea), but it was my wife's first trip under sail. She enjoyed the time and we have decided to go on more sailing trips. We were also able to celebrate our 35th wedding anniversary on board. We would like to thank you very much for the service on board and the highlights.
Read the full reviewGert and Birgitt after their trial cruise on the RHEA off Malta -
We had a fantastic vacation that we will look back on fondly
It was in 1 word: Great
It was in 1 word: Great. We really enjoyed this trip with KAIRÓS. Everyone was super friendly and they tried more than 100% to make us feel comfortable. And they succeeded. We had a fantastic vacation that we will look back on fondly.
Read the full reviewBertie and John after their trip to the Aeolian Islands
Experience Mediterranean joie de vivre on board our yachts
Discover our sailing trips through the Lipari Islands
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We have the answers for you
FAQs about sailing trips from Sicily
Das Revier rund um Sizilien und die Liparischen Inseln eignet sich besonders für Reisende, die Natur, Kultur und abwechslungsreiches Segeln verbinden möchten – von Vulkanlandschaften bis zu historischen Küstenstädten. Durch teils offene Etappen zwischen den Inseln ist es etwas lebendiger als ruhige Inselreviere. Da die Yachten mit professioneller Crew fahren, ist keine eigene Segelerfahrung nötig.
Vor allem Stromboli zählt zu den aktivsten Vulkanen Europas und zeigt regelmäßig sichtbare Eruptionen, die sich bei der Passage in der Nacht besonders eindrucksvoll beobachten lassen. Auch Vulcano ist vulkanisch geprägt und für seine Kraterlandschaft und schwefelhaltigen Quellen bekannt. Die Vulkane sind ein zentraler Höhepunkt eines Törns im äolischen Archipel.
Die Wanderung zum Krater von Vulcano ist für normal fitte Gäste gut machbar und dauert je nach Tempo in zwei Stunden hin und zurück. Empfohlen werden festes Schuhwerk, ausreichend Wasser und Sonnenschutz. Oben belohnt ein weiter Blick über den äolischen Archipel und das offene Meer.
Die Reisen starten je nach Route in Palermo oder Syrakus auf Sizilien. Die Anreise erfolgt über die Flughäfen Palermo (PMO) oder Catania (CTA), von denen der jeweilige Einschiffungshafen in kurzer Zeit per Taxi oder Transfer erreichbar ist.
Ja, die Route eines Segeltörns rund um Sizilien wird flexibel an Wind und Wetter angepasst, statt einem starren Fahrplan zu folgen. So lassen sich die besten Segelbedingungen und die schönsten Buchten ansteuern. Die ausgeschriebenen Häfen bilden den Rahmen, die konkrete Tagesplanung legt die Crew gemeinsam fest.
Landausflüge und Badestopps gehören bei einem Segeltörn rund um Sizilien und die Liparischen Inseln fest zum Programm. Es gibt Badestopps in klaren Buchten sowie Landgänge auf Lipari und Vulcano, die Wanderung zum Krater und bei Routen ab Syrakus den eleganten Küstenort Taormina mit Blick auf den Ätna. Wie viel Zeit auf Baden, Aktivitäten oder Kultur entfällt, richtet sich nach Route und Wetter.
Für einen Sommer-Segeltörn rund um Sizilien empfehlen sich leichte, bequeme Kleidung, feste Schuhe für Landausflüge, Badebekleidung, eine leichte Windjacke sowie Sonnenhut und Sonnenschutz. Am besten eignet sich eine weiche Reisetasche statt eines Hartschalenkoffers. Handtücher, Shampoo und meist auch Sonnenschutzprodukte sind an Bord bereits vorhanden.
Die Doppelkabinen bieten Stauraum über einen Kleiderschrank, Ablagen und Platz unter den Betten – ausreichend für das Gepäck einer ein- bis zweiwöchigen Reise. Da der Platz wie auf jeder Yacht begrenzt ist, eignen sich faltbare Reisetaschen besser als Hartschalenkoffer. Die Kabinen sind klimatisiert und verfügen jeweils über ein eigenes Bad.
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