Summer Sailing Special
Save 20% on your bareboat or skippered charter if you depart between now and November 30, 2026.* Book by June 1, 2026.

Cruising Licenses
ASA 104 | US Sailing “Bareboat Cruising Course” | SLC, IPC, ICC
Sailing Experience
At least 10 days or 200 miles as skipper on an equivalent size yacht
When it comes to your vacation, only the best will do. Speak with a Vacation Planner to begin your journey towards your next exceptional charter escape.
Save 20% on your bareboat or skippered charter if you depart between now and November 30, 2026.* Book by June 1, 2026.
Plan ahead and save 10% on charters departing between March 30, 2027 and November 30, 2027.* Book by June 1, 2026.
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Indulge in pristine swimming conditions at the island of Vulcano, feast your eyes on Europe’s second-largest active volcano at Stromboli, and explore the UNESCO-protected snorkeling sites. Featured in our Sicily sailing itinerary, each of these attractions offers opportunities for effortless adventure, deep relaxation, and time well spent on the water.
Choose your perfect Sicily sailing itinerary with The Moorings today.
Discover the best of Sicily with SailEATtalia’s Sail, Wine & Taste of Italy flotilla. Depart from our base in Portorosa and sail to the stunning Aeolian Islands to explore the local cuisine. One day during your Sicily flotilla vacation you will have the opportunity to learn how to prepare a typical Italian dish with a freshly made meal for your entire crew.
The beauty of a yacht charter in Sicily lies in the freedom to move at your own pace, in your own way. When you book a Sicily sailing vacation with The Moorings, you can choose between a bareboat, skippered, flotilla, or crewed charter, each one offering a unique way to experience the Mediterranean.
Discover our exceptional charter types today, and choose how you’ll explore the treasures of Sicily.
A bareboat sailing charter allows the opportunity to charter a yacht yourself whilst delivering a private yacht experience on the water.
A luxury crewed yacht charter delivers the ultimate all-inclusive vacation on the water aboard your own private sail yacht or power catamaran.
One of the most important decisions you will need to make before booking your yacht charter in Sicily is which type of yacht you want to set sail on. We are proud to have an impressive fleet of award-winning yachts designed for comfort, performance and ease on the water available in Sicily, including spacious catamarans and sleek monohulls.
View our fleet of innovative and stable sailing catamarans.
View our fleet of comfortable, performance monohulls.
The Moorings is honored to receive recognition for its fleet and vacation planning services. Awards include TripAdvisor Traveler’s Choice Awards 2025, 2024 and 2023, and The British Yachting Awards 2023.
What makes us stand out as the leading provider of yacht charters in Sicily is the freedom to build your dream vacation. You can choose one of our carefully crafted itineraries, or create your own one and sail a bespoke route around the Aeolian Islands.
If you follow one of our routes, you can expect to visit breathtaking islands such as Vulcano, Salina, and of course Portorosa.
A Sicily yacht charter offers superb cruising conditions with clear waters, consistent northwest to westerly breezes, and warm temperatures during peak season.
Gentle wind speeds averaging 6 knots persist throughout the year, making it easy to capture a relaxing sailing vacation set against a picturesque backdrop. Enjoy brief commutes from one Aeolian island to the next while basking in the lush cliff-lined scenery that abounds in every direction.
The steady winds, beautiful temperatures and short passages make a Sicily yacht charter ideal for sailors of all skill levels, whether this is your first time taking the helm on a bareboat charter, or you already have plenty of time on the helm. To be able to charter a yacht in Sicily, and anywhere else in Italy, you must hold a valid sailing license in your country of origin. Learn more about our Italy sailing requirements and explore the best beaches in Sicily as part of your itinerary.
Named after Aeolus, god of the winds, the volcanic-formed Aeolian Islands intrigue the senses in all the best ways.
If you’re looking for a sailing vacation with breathtaking landscapes and lush green spaces to complement the stunning blue waters, you will love a Sicily yacht charter. Nature lovers and hiking enthusiasts will enjoy scenic treks along guided trails and the natural thermal springs never fail to deliver a unique and memorable travel experience. The beautiful mountain of Fossa Felci on Filicudi is a particularly incredible island to moor up at if you want to experience the natural wonders of Sicily.
Undeniably, a Moorings Sicily yacht charter is about exquisite cuisine. Fresh, authentic, and bursting with flavour, Sicily boasts delicacies such as delicate cannolis, piquant caponata, savory arancini, and much more. Read our recent blog on sailing in the Tyrrhenian Sea to learn more about what makes setting sail around Italy such a unique experience, and why a Sicily yacht charter should be your next vacation.
The peak sailing season in Sicily, and Italy as a whole, runs from April to October, with April-May and September-October being the best times for a Sicily yacht charter if you want to avoid the Summer crowds.
It is important to note that our Sicily sailing charter base is closed between early-November and mid-March. If you are looking for a Winter sailing vacation, take a look at our Caribbean destinations such as the BVI and St Lucia.
A Sicily yacht charter offers plenty of incredible opportunities for island hopping around Italy and the Aeolian Islands. Our Sicily sailing itinerary takes you to incredible islands, including:
Whether you take the helm on a bareboat charter in Sicily, or hire a skipper to navigate you around the passages between islands, you will have the unique opportunity to discover sensational islands and create magical memories.
We think a Sicily sailing charter of at least 7 days is ideal because it gives you the opportunity to uncover the treasures of the Aeolian Islands, while also having the time to relax, unwind and sip cocktails in the sun. Depending on how many excursions you want to go on, which islands you want to explore and how much downtime you’d like, you may choose to extend your Sicily sailing vacation to longer than 7 days.
If you have any questions about any of our itineraries, get in touch with us today.
If you love spending time in the water with friends, family or as a couple, take a look at our water sports options.
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