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Circumnavigating Sicily: 500 Miles Over Three Seas

Day 1: Palermo to San Vito Lo Campo

Depart from the lively capital city of Palermo to San Vito Lo Capo, a small town nestled between spectacular mountains, famous for the international Cous Cous Fest and dotted with charming seaside restaurants. Enjoy a classic dinner of fish couscous complimented by a fine local wine.

Day 2: San Vito to Erice

Sail from San Vito to the historic town of Erice located 750 meters above sea level. There are two castles and impressive ancient ruins worth visiting. Savor luncheon al fresco at anchor on your before navigating to Favignana, popular for diving and snorkeling. Dive into the ocean in the afternoon then prepare to explore the town and anchor for the night.

Day 3: Favignana to Marsala

Favignana is famous for bluefin tuna caught using ancient Arab techniques, and caves of calcarenite rock. Visit the tuna factory, do a bit of shopping and play in the sparkling sea. In the afternoon depart for Marsala, a short distance of 10 miles. Drop anchor in Marsala Lagoon and visit the windmills of Mozia Aperitif. Visit the old town at sunset for spectacular views and explore the ancient market of Marsala.

Day 4: Marsala to Porto Empedocle

The cruise from Marsala to Porto Empedocle passes 66 miles of spectacular coastline and is an awe-inspiring voyage by power or sailing yacht. There are several port towns and lovely beaches that are perfect for shore excursions. Moor in Porto Empedocle that lies on the coast of the Strait of Sicily and is steeped in culture and history.

Day 5: Agrigento and Cala dei Turchi

This morning visit the Valley of the Temples in Agrigento. The Greek pre-socratic philosopher Empedocles was a citzen of this ancient Greek colony. Sail to Cala dei Turchi with its sweeping sandy beach and towering cliffs in a picturesque cove, the place of ancient Arab pirate landings in Sicily. The surrounding sea is incredibly transparent and offers superb grotto diving. Cocktails and dinner on board your elegant crewed charter yacht and a night transfer to reach Marina di Ragusa.

Day 6: Ragusa

Ragusa is listed with seven other cities in the Val di Noto as a UNESCO World Heritage Site. The city is a thrill for history, art and architecture enthusiasts, with origins that can be traced back to the 2nd millennium B.C. From the noteworthy collections of the Hyblean Archaeological Museum to fabulous Baroque and Rococo architecture, Ragusa is an extraordinary destination.

Day 7: Syracuse via Portopalo di Capo Passero

Depart Ragusa for Syracuse via Portopalo di Capo Passero, whose strategic position has fostered it’s development since ancient times as a crossroads of civilization and culture for all seafarers that bravely challenged the Mediterranean Sea. The scenery viewed from the deck of a yacht is simply breathtaking. Explore the artisan shops and markets and marvel at eclectic architectural styles. In the evening enjoy a romantic dinner at a harbor restaurant in Ortigia.

Day 8: Syracuse, Day 9: Taormina and Mount Etna

Syracuse, also a UNESCO World Heritage Site, is an amazing repository of Greek history, culture, amphitheatres, architecture, and is mentioned in the Bible because the Apostle Paul spent time here. There are also wonderful museums, shops and restaurants offering far more to do than can be done in a day.

Navigate to Taormina where the yacht will moor in the picturesque Bay of Giardini Naxos, a popular seaside resort. The village of Taormina is perched on a cliff overlooking the warm waters of the Ionian Sea. Visit the ancient Greek theatre, remarkable for its state of preservation and location. Stroll among buildings and churches centuries old, lively bars, fine restaurants and antique shops, all of which contribute to Taormina’s allure. Taormina is approximately a forty-five minute drive away from Europe’s largest active volcano, Mount Etna.

Day 10: Messina, Day 11: Milazzo

Depart for Messina, the third largest city on Sicily. Founded by Greek colonists in the 8th century BC, Messina is characterized by landmarks, museums, restaurants, shops, beautiful fountains and splendid squares at every turn.

Embark upon the 35 mile passage through the Straits of Messina to Capo di Milazzo, a thin peninsula that extends into the Tyrrhenian Sea. This is the site where several civilizations have settled beginning in the Neolithic age, and the site of Ulysses shipwreck and fated meeting with Polyphemus. The port of Milazzo is a departure point for ferries to the Aeolian Islands and Naples.

Day 12: Aeolian Islands

The magnificent Aeolian Islands are well worth a week long charter in and of themselves. This volcanic archipelago in the Tyrrhenian Sea is a very popular tourist destination with good reason. Here the weather will help decide which islands to visit and what adventures to pursue. Visit the fascinating pumice quarry and plan for an excursion to Capofaro Malvasia Resort, situated under the lighthouse from which it takes its name, on Salina, the Aeolian Island with the greenest and most luxuriant vegetation. The Regaleali Estate is renowned for Tasca d’Almerita award winning wines and a restaurant offering typical Sicilian dishes prepared with estate grown produce.

Day 13: Aeolian Islands to Cefalu

Depart the Aeolian Islands for the 55 mile journey to Cefalu. Enjoy a delicious lunch on board while docked in the Bay of Cefalu. The town is one of the major tourist attractions in the region with a young atmosphere and lively nightlife. The villages are attractive for artistic, cultural and historic reasons. Dinner can be enjoyed at a local restaurant on the sea.

Day 14: Return to Palermo

Time to return to Palermo and bid your captain and crew farewell. If possible plan to spend at least a day here in Sicily’s cultural, economic and tourist capital. Visitors delight in the extraordinary restaurants, splendid Romanesque and Gothic architecture, palaces, museums, theatres and fine shopping. occupy a seat at an outdoor cafe, sip a real Italian cappuccino and consider your next destination for a luxury yacht charter vacation.

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