Sicily 14 Day Sailing Itinerary 

This itinerary can be sailed from either Palermo or Portorosa.

Day 1 – Palermo

Sicily's main city is draped in a mantle of unpredictability and adventure: its streets are chaotic and its buildings are magnificently dishevelled. We’d recommend a thorough look around Palermo starting in the old city where you will find a wide mix of architectural styles thanks to the wave upon wave of invaders.

  • Day 2 – Cefalu

    Cefalu is most famous for its two-towered Norman cathedral which dominates the town’s rooftops. Inside the cathedral you’ll find an interior decorated in lovely mosaics dating back to 1138. Towering above the town is a massive crag called the Rocca. The climb to the top is hard but the views make the effort well worth while!

  • Day 3 – Vulcano

    Vulcano's volcanic nature has long been impressing visitors – the ancient Romans believed it to be the chimney of the fire god Vulcan's workshop and the island is today celebrated for its therapeutic mud baths and hot springs. The main drawcard however, remains the Fossa di Vulcano, or Gran Cratere (Large Crater), the steaming volcano that towers over the island's north eastern shores.

Day 4 – Panarea

The ancient island of "Euonimo" is 3.5 sq km and is predominantly focussed on luxury tourism. The main village, Contrada San Pietro, consists of a picturesque group of white houses clustered along the eastern side of the island. The built-up area is crowned with olive trees and protected by huge walls.

  • Day 5 – Stromboli

    Emerging out of the blue haze like a menacing maritime pyramid, Stromboli's smoking silhouette conforms perfectly to one's childhood idea of a volcano. In fact, the island of Stromboli is just the tip of a vast underwater volcano that rises from the seabed 1476m below. The most captivating of the Aeolian Islands, it's a hugely popular daytrip destination as well as the summer favourite of designers Dolce and Gabbana.
  • Day 6 – Salina

    Salina is the second largest island in the Aeolian group. In stark contrast to the exposed volcanic terrain of the other Aeolian Islands, Salina boasts a lush, verdant landscape. Woodlands, wildflowers, thick yellow gorse bushes and serried ranks of grape vines carpet its hillsides in vibrant colours and cool greens, while high coastal cliffs plunge into the breaking waters below.

Day 7 – Filicudi

Filicudi measures less than 10 square kilometres and is the most ragged of this group of islands. It’s a quiet holiday island and the two small villages lie on a small peninsula stretching out towards the south. Remains of prehistoric settlements from the Bronze Age have also been found here.

  • Day 8 – Alicudi

    Alicudi is known as the ‘Island of Heather’ due to the pink blanket that covers its lavic surface in spring. This is the smallest and western-most of the inhabited Aeolian Islands and lies about 67 miles from Milazzo. Near the village there is a rise called "Timpone delle femmine' where women used to be hidden to prevent them from being kidnapped by the pirates during their raids.

  • Day 9 – Isola Delle Femmine

    The English translation of Isola Delle Femmine means “The Island of Women” which is a little misleading as the town is actually located on mainland Sicily. It’s thought that the name originated in the 19th century when a plague slept through the local area and women and children were sent to the island just off the mainland in order to protect them. 


Day 10 – Levanzo

Levanzo is the smallest of the three islands, covering an area of 5.82 square kilometres. The island has approximately 450 inhabitants who are concentrated around a tiny port. Levanzo is famous for the Grotta del Genovese with Neolithic cave paintings of animals and human figures.

  • Day 11 – Marettimo

    Marettimo probably gets its name from the profusion of thyme on the island (mar – sea, timo – thyme) and is considered the most laidback of the three Egadi islands. It was an important observation point during the Roman times, hence the Casa Romana where it was easy to observe passing maritime traffic.
  • Day 12 – Favignana

    The island of Favignana in situated approximately 7 kilometres west of the coast of Sicily and is the largest of the three principal Egadi Islands. It is famous for its tuna fisheries. Its name is derived from Favonio, an Italian name for the foehn wind.

Day 13 – San Vito Lo Capo

This town is located in a valley between two amazing mountains and is home to a well-known beach with is popular with the locals. The mountains are popular with climbers and have plenty of caves, unfortunately most of these need climbing gear to be accessed. If you happen to be visiting in May we recommend going to the beach as an International Kite Festival is held there. 

Day 14 – Palermo

As with much of Sicily there is always more to a place than meets the eye. Palermo is no exception and we recommend you take the time to explore the back streets away from the bustling town centre to really appreciate what this town has to offer.