A 7-day itinerary to discover the wonders of Sicily on your sailboat

If you are looking for a destination for your next sailing vacation, Sicily is definitely a must-see destination. With its rich history and culture, over the centuries the island has been influenced by different peoples, creating a unique combination of traditions and lifestyles.

In addition to culture, Sicily also offers a delicious local food and wine tradition, characterized by intense and genuine flavors, and breathtaking landscapes. The warm welcome of the locals will make you feel immediately at home, making you fall in love with the island and all it has to offer.

Renting a catamaran or sailboat will allow you to explore every corner of this incredible island. By boat you will have the opporunity to experience Sicily from a unique and unforgettable perspective. From the east coast to the west, the coasts are dotted with dreamy beaches, unmissable views, and itineraries full of history and charm. You can visit magnificent cities such as Palermo, rich in history, architecture and jaw-dropping views; Cefalù, with its imposing Fortress and its cinematic fishermen’s quarter; San Vito Lo Capo, with its crystal clear waters and unspoiled nature; Scopello, with its striking Tonnara and majestic Faraglioni rocks.

Choosing Sicily as your sailing vacation destination means immersing yourself in a fascinating culture that will give you an unforgettable experience. Dive with Spartivento Charter to discover this Mediterranean treasure!

Map itinerary 7 days sailing in Sicily with Spartivento Charter

Day 1: Cefalù
Departing from the base in Portorosa or Capo D’Orlando, your route to Cefalù, a city in the Madonie Park and among the most beautiful villages in Italy, will take you on a journey through art, culture and history. The name Cefalù derives from the Greek Kefaloidion, in reference to the peculiar shape of the rock that towers above the city.

Its architecture reflects the domination of different peoples over the centuries, as evidenced by the crenellated walls and barracks from the Byzantine era alongside the regular urban structure from the Roman era. Beautiful sandy beaches, rocks, and clear, sheltered waters make Cefalù one of the most beautiful seaside destinations in Sicily.

View from the sea of the beach and the town of Cefalù in Sicily

Day 2: Palermo

The itinerary continues in the direction of Palermo, the beautiful capital of Sicily. Along the way you will have the opportunity to stop at Mazzaforno Bay, home to the picturesque Seven Friars Beach. This picturesque scenery enchants visitors and tourists with its extraordinary charm. You can also snorkel and swim in these crystal clear waters, admiring the incredible variety of sea hues ranging from emerald green to turquoise in the deepest parts.

We then proceed to Palermo, a veritable open-air museum full of monuments, churches and works of art. The city is characterized by a mixture of architectural styles, from Arabian beauty to Baroque works. Its calm chaos and quaint markets are what makes it unique. Among the city’s many attractions, it is impossible not to visit the majestic Cathedral, a perfect symbol of the city’s thousand-year history.

Sunset view of the entrance to Palermo Cathedral in Sicily
Cathedral of Palermo

Day 3: Castellammare del Golfo

Depart from Palermo to reach Castellammare del Golfo, a picturesque coastal town that offers a splendid view of the Gulf of Castellammare. With its cobblestone streets and colorful buildings, Castellammare del Golfo offers a unique atmosphere, with numerous cultural attractions to explore including the Arab-Norman Castle and the Mother Church.

Castellammare del Golfo is a perfect base for exploring the northwest coast of Sicily, characterized by numerous coves, caves, and hidden beaches that can only be reached by boat. Spend a day of sea and relaxation among the enchanting waters of Guidaloca Beach or Cala Bianca Beach, both of which can be reached by sailing a few miles westward from the town.

Toward evening, return to the harbor and be carried away by the scents and flavors of Trapani’s seaside village. Don’t miss the Pane Condito, one of the most iconic gastronomic specialties of Castellammarese cuisine!

Panoramic view of the port of Castellammare del Golfo in Sicily, Punta Raisi in the background
Castellammare del Golfo

Day 4: Scopello & San Vito Lo Capo

The following morning you will leave for San Vito Lo Capo. On the way, you won’t be able to resist diving between the majestic Faraglioni of the Tonnara di Scopello, where in summer you can take advantage of the buoys to moor at anchor. Continuing along the coast, you can stop for a refreshing swim in one of the countless coves of the Zingaro Nature Reserve: Cala Capreria, Cala del Varo, Cala della Disa, Cala Marinella, Cala dell’Uzzo, one more beautiful than the other!

Crystal-clear waters and white sandy beaches surrounded by unspoiled nature await you in St. Vitus, accompanied by a noteworthy dining experience with a wide selection of delicious local dishes. Hiking and walking enthusiasts will have several paths to the top of Mount Monaco, where they can admire the remains of a marble quarry.

Panoramic view of the Tonnara and the Faraglioni of Scopello in Sicily
Tonnara of Scopello

Day 5: Palermo

Departing from San Vito Lo Capo in the direction of Palermo, we recommend a short stop for a dip in the crystal-clear waters of the Gulf of Mondello, home to Palermo’s most beautiful and iconic beach.

During your visit to Palermo, you can devote yourself to exploring everything you have not yet seen or done during your previous stop. You will have the opportunity to stroll through the downtown districts, such as Ballarò and the Kalsa market, go up to the Norman Palace to discover the wonderful Palatine Chapel.

If, on the other hand, you want to experience Palermo’s vibrant culture, we recommend a trip to the Vucciria, the capital’s historic market, where you can fully immerse yourself in the city’s chaotic and authentic atmosphere.

Panoramic view from the ground of Mondello Beach in Palermo, Sicily
Mondello Beach

Day 6: Cefalù

On the fifth day of your trip, you will return to Cefalù making a stop at the Grotto of Santa Lucia, which can only be reached by sea, to enjoy a refreshing swim in crystal clear, transparent waters.

Once at the port, we recommend you take a walk along the waterfront and reach Porta Marina, the only remaining gate of the four that once provided access to the city. From here you can admire the sunset over the sea and the picturesque fishermen’s quarter, the set of Tornatore’s very famous 1988 film “Nuovo Cinema Paradiso.”

For hiking enthusiasts, an experience not to be missed is the ascent via a picturesque path surrounded by greenery and enclosed by medieval walls to the Rocca di Cefalù, a spectacular 268-meter-high cliff that rises behind the town. The rock, which is limestone in nature, is home to many species of local flora and fauna, including conifers and eucalyptus trees. From the summit you can enjoy a spectacular panorama from Palermo to Capo D’Orlando.

Panoramic view of the Rock of Cefalù in Sicily
Rock of Cefalù

Day 7: Tindari Bay & Return to Base

When the time has come to take the return route back to base, you will make your way to Capo D’Orlando or Portorosa. Along the way, we recommend a stop for a rejuvenating swim in the beautiful Tindari Bay. Portorosa is the largest marina in Sicily and offers enchanting villas surrounded by greenery, as well as navigable canals that host numerous moorings. Capo D’Orlando, known for its crystal clear waters and golden sandy beaches with slowly sloping shallows, is a city rich in history, with ancient Greek and Roman ruins and a fascinating historic center to explore.

View from shore of the Tindari Beach in Sicily
Tindari Beach