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Italy - Aeolian Islands & Sicily Yacht Charter Itinerary

Sail from Medieval Villages to Fuming Volcanoes and Sulpher Mud Baths – All in Crystalline Seas

The mountain fringed coastline is a dramatic backdrop for cobalt blue seas and the historic cities that nestle into the harbor’s edge. Your Sicily vacation itinerary can include the chic cities of Portorosa, Taormina and Messina as well as the volcanic archipelago of the Aeolian Islands – often referred to as the Holy Grail of Mediterranean islands. The Aeolians – a secret and untamed cluster of seven major islands with postcard villages, rugged mountains, smoking volcanoes, spectacular vistas, and sparkling waters.

For those who want more remote ports and yacht-centered adventures, we recommend the following Sicily vacation itinerary:


  • Day 1 Palermo

    Your Sicily vacation itinerary begins in the coastal city of Palermo, the Capital. The city is stupendously located in its own wide bay underneath the limestone bulk of Monte Pellegrino. Poke about the medieval streets and markets. Tour the medley of piazzas, palaces, chapels and churches. Sample a cannolo – that sweet packed ricotta roll that was birthed in Palermo. Salute the setting sun at the Grand Hotel Villa.z

  • Day 2 Ustica

    Day Two of your Sicily vacation itinerary dawns early as we cast off for the island of Ustica, the tip of a submerged volcano. Only about 10 square miles in size, Ustica is a diver’s paradise – a marine preserve with red gorgonian fan coral, rainbow sponges, stunning underwater grottos, and archeological artifacts. Currents from the Atlantic produce crystal waters and provide a welcoming habitat for schools of fish and a medley of flora and fauna.

    Climb in the yacht’s tender and explore the fabled caves, hike to some ancient ruins, and sample farm to table cuisine at local restaurants. The shoreside village is a patchwork of quaint homes colorfully adorned with hand painted murals.

  • Day 3 Alicudi / Filicudi

    Day three of your Sicily vacation itinerary brings you to the first of the Aeolian Islands and also the most untouched by tourism - Alicudi and Filicudi. The twin islands of tranquility. Secluded anchorages, sparsely populated, and wild heather clinging to the hillsides – Mother Nature is the main attraction here. Snorkel the grottos with luminous glows. Kayak along the rugged shoreline of craggy ridges and artistic rock formations.. Stroll into the quaint town where donkeys still assist with the transport of local goods. Or just relax on deck and watch the day unfurl at a snail’s pace, marvel at the dramatic ridges and fissures formed by volcanic activity and eroded into fantastical shapes.

  • Day 4 Stromboli

    The rock star of the Aeolians, smoldering with smoke in a purple haze in the daytime and spewing flames and ash into the sky in the evening. The world’s oldest, continuously active volcano juts into the sky about 10,000 feet above sea level. The intrepid can join a heart pumping guided tour to the crater’s edge . As darkness descends, the belch and boil of the magma in the crater with lava fragments exploding tingles the senses. If you prefer a more sedate viewing with Prosecco and caviar, relax on deck and enjoy the light show. Either way, you’ll have memories for a lifetime. On a Sicily vacation itinerary, our encore performance is a short cruise to the nearby island of Panarea.

  • Day 5 Panarea

    Panarea, the smallest and most cosmopolitan Aeolian, can be whatever you want it to be. For some, it’s a jet set “let’s party” island, and tourists land on its shores with unbridled revelry on their minds. If you want to dance at a rooftop bar til dawn, this is mecca for you. But there is a sleepy side to this charming island as well – most of the cobblestoned streets are closed to traffic, no rental cars (except electric), picturesque white houses, bougainvillea lined paths, and brilliant yellow ginestra bushes. On a Sicily vacation itinerary, your charter yacht will anchor in crystal-clear waters at the foot of a pre-historic village 1300 BC. We recommend hiring a scooter and touring the island.

  • Day 6 Salina

    Salina, the Garden Island, is a lush, verdant island. Whereas its neighbors have scraped volcanic hillsides, Salina shimmers a dozen shades of vibrant greens - thick with farmlands, vineyards, and wildflowers. Produce and vineyards reign supreme here, and the local specialties are its famous Malvasia dessert wine and the plump, local caper. Both are celebrated annually. Home to the highest mountain in the island, the dramatic cliffs plunge to the sea and offer numerous hiking trails. On a Sicily vacation itinerary, the island’s secondary claim to fame is that the Academy Award winning film, Il Postino, was shot in the village of Pollara – the best place on the island for viewing the sunset. Rent a scooter, make a spa date, enjoy a seaside lunch, swim, soak, shop.

  • Day 7 Vulcano / Lipari

    Famous for the mud baths (‘fanghi’) and its smoking main crater, you can often smell the pungent sulfur of the island before the anchor is dropped. But it is well worth the walk up to the impressive crater

    Nearby Lipari is the largest of the Aeolians with quaint shopping streets, produce markets and the Aeolian Archaeological Museum which simmers with Mediterranean history. Another great island for a scooter tour or just to enjoy the pleasures of yachting – anchoring in a secluded bay and breaking out all of the toys.


  • Day 8 Milazzo

    Late morning, your yacht will drop you off in Milazzo for a transfer to the airport.

Our Expert Opinion

Combining the spirited cities of Sicily with the dramatic Aeolian islands offers a charming blend of history, culture and unabashed nature. The ascent to the crater’s edge of very lively Stromboli volcano is a peak experience… a must for your bucket list. Or just relax on the deck of your yacht, sipping a local Malvasian wine as Stromboli spews its molten lava into a star-flooded sky.

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