Sail Sicily and its offshore islands

Sail in any Direction, and Expect the Unexpected 

Northern Sicily

Sicily, Italy's largest island, spans 25,706 square kilometers (9,925 square miles) and holds the title of the largest island in the Mediterranean Sea. Its strategic location at latitude 38° north has made it a prized conquest for countless invaders over the centuries, including the Greeks, Phoenicians, Romans, Arabs, Normans, and Spaniards. Each of these cultures has left its mark, creating a rich blend of influences that give Sicily its unique personality, reflected in its architecture, cuisine, and customs. A visit to Sicily is truly a treasure, and that’s before even considering the incredible sailing experiences it offers.

Sicily is dotted with beautiful bays and ports worth exploring, and the Aeolian and Egadi island groups are also major attractions for travelers, making this a vast sailing destination that’s difficult to fully explore in just seven or even 14 days. Many charterers focus their sailing holiday on the northern coast, visiting cities like Palermo, the historic Cefalù, and the charming Portorosa. However with a little planning, two entirely new worlds open up for discovery.

Using Palermo as your northern base, it’s just a short sail to either or both of these island groups with a scenic cruise along the coast. You can visit the picturesque towns of Castellammare del Golfo, Trapani, and Marsala to the west, or explore the medieval town of Cefalù and the alternative base of Portorosa to the east, each offering unique charm and beauty to enhance your sailing adventure.

The Aeolian Islands

Rising from the Tyrrhenian Sea about fifteen miles off the Sicilian coast, the Aeolian Islands—Lipari, Salina, Stromboli, Vulcano, Panarea, Filicudi, and Alicudi—are a stunning destination for a yacht charter. With their black volcanic beaches and the dazzling clarity of the Mediterranean light, these islands offer everything needed for an unforgettable sailing experience.

The history of this UNESCO World Heritage Site dates back at least 5,000 years, with traces of ancient human presence found in prehistoric villages, ruins, excavations, pottery, and tools. The volcanic landscape creates a dramatic setting—one writer described it as “Fire above and below,” with the islands basking in the relentless heat of the Sicilian sun.

Colorful fishing boats line the lively ports, surrounded by charming cafes, bars, and restaurants. While the islands’ interiors feature diverse and contrasting landscapes, the crystal-clear waters of sheltered bays and coves, volcanic activity, isolated reefs, brightly painted houses, and archaeological sites make for a truly spectacular backdrop. The food and wine here are exceptional, and some of the islands offer the rare charm of being almost vehicle-free, providing a peaceful retreat from the hustle and bustle.

Sailing in the Aeolian Islands offers a sense of escape, far from the crowded tourist routes. While the islands have long been a beloved holiday spot for Italians, the rest of the world is only just discovering their unique allure.

Consider combining your trip to the Aeolian Islands with a tour of Sicily, or use the 16th-century Calabrian town of Tropea as your base to explore this extraordinary Mediterranean charter holiday destination.

The Egadi Islands

Lying just to the west of Sicily, the Egadi Islands are becoming a sought-after addition to sailing itineraries when time allows.

Often overshadowed by the more famous Aeolian Islands, the Egadis remain a hidden gem on the sailing map. These small islands have preserved much of their natural beauty and historical charm. On a charter here, you can expect to find secluded bays perfect for anchoring, deserted mountain trails to explore, and a local population of around 5,000 who live at a wonderfully relaxed pace. As a sailing destination, the Egadi Islands offer an unmatched sense of tranquility and authenticity, making them an ideal choice for those seeking a truly serene and unspoiled escape.Read more about the Egadi islands here. 

Southern Sicily - west

If you’re limited on time but still want to experience the charm of Southern Sicily, the primary charter base in the area is Marina di Ragusa. From here, you can sail either west or east, depending on your preferences and schedule. To reach the Egadi Islands and fully enjoy their beauty, a full seven-day charter from Marina di Ragusa is recommended. Heading east, the distance to Reggio Calabria, located at the very toe of mainland Italy, is comparable. For a charter that combines both Southern Sicily and Malta, however, a two-week itinerary is ideal.

Sailing westward from Marina di Ragusa, you’ll find Licata, 35 nautical miles away. This town of 37,000 offers a modern marina and a genuine, friendly atmosphere, though it’s not a major tourist destination. All necessary services are available, and a walk to the 16th-century Castel Sant'Angelo, which overlooks the town, is a charming diversion. If you’re looking for a relaxing break, several lovely beaches along the coast provide the perfect spots for lunch and a swim. If you prefer a shorter journey, Gela, another quaint town nearby, offers an excellent overnight stop.

Continuing west, the next destination is Sciacca, about 50 nautical miles from Licata. This well-preserved town, with its Greek origins, is an important fishing port. Its marina is welcoming, and prices here are quite reasonable compared to more tourist-heavy areas. Another nearby option is the resort town of Porto Palo di Menfi, a large harbor with ample anchoring opportunities.

As you sail along the coast, you'll pass by the UNESCO World Heritage-listed Valley of the Temples at Porto Empedocle. Though the marina here is small and often busy, it’s worth planning ahead for a visit. A short taxi ride from the port will take you to one of the finest examples of ancient Greek ruins, showcasing Sicily’s rich classical history.

Along the way, you’ll also pass significant towns such as Mazara del Vallo, one of Italy’s largest fishing ports, Marsala, famous for its wine, and Trapani, which is an important charter base and the closest port to Sardinia. All these towns offer marina facilities, ensuring that you’re never far from the services you need during your sailing adventure in this fascinating part of Sicily.

Southern Sicily - east

Sailing east and then north from Ragusa, you'll find yourself in a region often considered to be the best of Sicily—an area where glorious baroque architecture contrasts with rugged landscapes. This is home to some of the island's finest beaches, exceptional wines, and unique culinary delights. Ragusa itself is an attractive town, well worth exploring, before you embark on your journey.

Your first stop on a Ragusa-based itinerary could be Marzamemi, a charming fishing village located just after rounding the southeastern corner of Sicily at Isola delle Correnti. Marzamemi is a picturesque old town with a marina and provisioning facilities, making it an ideal place to pause. From here, it's a short sail with a good breeze to the large natural harbor of Syracuse. Arriving early gives you more time to explore this famous example of Sicily’s timeless beauty. The town is filled with ancient ruins, and if you're visiting in late spring or early summer, you might even catch a performance at the Greek Amphitheater. Syracuse offers free stern-to mooring with anchor, making it a convenient and welcoming stop.

From Syracuse, the well-known destinations of Catania, Riposto, and Taormina are all within a leisurely day's sail. Each offers plenty of opportunities for exploration depending on how much time you have. In Catania, Sicily’s second-largest city, several yacht clubs offer hosting facilities. The old town is a UNESCO World Heritage site for its exceptional architecture. Further north, Riposto provides excellent overnight accommodations for boats, and the resort town of Taormina offers scenic coastal anchoring. There are also mooring options in Taormina itself.

Dominating the skyline above these towns is the brooding Mt. Etna, Sicily’s most active volcano. From any of these ports, you can easily access the culturally rich rural hinterland surrounding the mountain. While Etna’s constant activity means occasional ash falls, the fertile slopes of the volcano produce some of Sicily’s finest agricultural products, making it a treat for food lovers.

By now, you’ll have seen the best of southern and eastern Sicily. If you still have time on your seven-day charter from Ragusa, consider backtracking from Taormina to revisit places you may have missed earlier. Alternatively, continue through the Straits of Messina to reach the city of Messina. This port offers modern marina facilities for a convenient stopover. Alternatively, you can cross the strait to Reggio di Calabria on the mainland, just three miles away. Be mindful that anchoring is prohibited in the entire Straits of Messina area, so plan your stops accordingly.

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