Best of Sicily Tour 2019

A 9 day trip to Italy 
4.86 out of 5 stars
822 reviews

The majesty of Sicily will enrapture you with mythical tales, vibrant culture, indulgent cuisine, and ineffable history. Architecture seamlessly blends Arab and Norman influence. Markets present an atmosphere similar to a North African bazaar. The seaside glistens multiple shades of indescribable blue. The beauty of Greek ruins shares the spotlight alongside Baroque palaces. The wonderment of Mount Etna’s towering peak complements the five-star luxuries of your unforgettable accommodations. Designed for 2019, your custom-tailored best of Sicily tour encapsulates the splendors of Sicily, showing you marvelous vistas overlooking endless vineyards and preserved Roman mosaics providing insight into the lavish lifestyle of prosperous colonists.

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General Information

Detailed Itinerary

Places Visited 

Palermo, Agrigento, Erice, Segesta, Piazza Armerina, Modica, Ragusa, Taormina, Syracuse, Mount Etna, Reggio Calabria

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Passionate Palermo

Palermo is a city of splendor that encapsulates the history of Sicily. Vibrant cultures have influenced the city and the traditions of the locals for millennia. Historic structures glint gold in the sunlight. The city is draped in adventure, from the narrow medieval streets to the wide, proud boulevards. Your private transfer meets you at the airport and escorts you to your lavish accommodation located in the heart of the historic center. Consider learning more about your tour operators for Sicily, and read precisely  how they are able to perfectly craft your an itinerary to your desires. The vibrant markets showcase the melting pot past of the city. Tarps cover the stalls. Vendors call out to passersby. The bright colors of fresh produce, from bananas to pomegranates, burst from the stands.

When walking between the antique buildings it feels as though you have wandered into North Africa rather than strolling along a European cobblestone lane. Graceful architecture and imposing churches encircle the Piazza Pretoria. However it’s the Fontana Pretoria that is the center of attention in the square, a fountain with tiered concentric circles forming the base. Statues of nymphs, tritons, and leaping river gods decorate the elegant 16th-century structure. The neoclassical décor adds to the illustrious figureheads decorating the fountain and speaks to the ancient Greek history spanning the island. It now adorns the façade of Municipal Hall.

What’s Included: dinner, transfer, accommodation

Day 2: Mediterranean Bridge

In the morning, you find the aroma of rich espresso accompanying the traditional sweet scent of brioche. The fragrance of citrus lingers in the breeze, deriving from the wild orchards growing around the city. After breakfast, your guide meets you at the hotel and escorts you on a sensational tour of Palermo, showcasing the assortment of Mediterranean life that once called Sicily its home. The Palermo Cathedral was erected in the 9th century as a mosque but rebuilt in the 12th century after the Norman invasion. The blind arches and tin-glazed pottery depict mythical scenes, highlighting the Arab-Norman architecture around the city.

The 13th-century gem-encrusted crown of Constance of Aragon is on display inside the cathedral near the marble shell of the royal Norman tombs. You can find elements of the original mosque at the southern porch where a Koranic passage was inscribed in a column. The grandeur of the cathedral and its rich historical properties are captivating, bringing you to the doorstep of Sicily’s illustrious past. Inside the Norman Palace, you find the Byzantine gold leaf mosaics glittering from the natural light pouring in through the dome. The vaulted arches and depictions of saints bring an ethereal calm to the interior.   

What’s Included: breakfast, lunch, tour, accommodation

Day 3: High on the Medieval Hill

The beauty of Palermo returns in the morning with the opening of the markets. The vibrant life on the streets of the city is enriching. The aroma of fresh made arancini, traditional deep fried rice balls, drifts along the cobblestone streets. At breakfast, you find the indulgent flavor of fresh cappuccino waiting for you. Your private transfer meets you in the lobby and leads you away from the city to the base of legendary Mount Eryx. The summit rises 2,460 feet above sea level, overlooking the port of Trapani. A scenic gondola ride takes you to the top of the mountain, where the sensational medieval town of Erice awaits. The undulating landscape sweeps from the seaside to the hillsides, filled with olive groves, citrus orchards, and vineyards.

The plateau was once home to a Hellenistic town dedicated to Aphrodite. Cobblestone streets dissect the buildings on a grid along the triangular shaped summit. The Chiesa Matrice was erected in the 14th century and has a large rose window adorning the façade, allowing natural sunlight to pour into the nave. Architects took stone from the ancient buildings to help erect the church and the defensive towers around town. The Norman Castle of Venus was constructed over the Temple of Venus, and provides spectacular views of the protruding rock face of San Vito Lo Capo and the port of Saline di Trapani. The white sand beaches shimmer in the drifting light.

What’s Included: breakfast, lunch, transfer, tour, accommodation

Day 4: Captivating Ancient Artwork

In the morning, you wake up to a view of Greek ruins strewn along the landscape. Outside of the modern town of Agrigento lies the Valley of the Temples, know for the remarkable remains of Doric structures dating as far back as the 6th century BC. Columns rise along the hilltops and around the base of the dell. Citrus orchards provide a luscious aroma to the landscape. Shepherds herd their sheep along the creek bed. The Temple of Juno was erected in the 5th century. It is six columns wide and 13 columns long. The frontal beam remains poised atop two pillars. The ancient past comes alive with the remains of the architectural marvels of a distant civilization.

You continue to the Villa Romana del Casale, an estate established in the 4th century AD. Part of the villa was encased in a mudslide, which helped preserved some of the elaborate mosaics depicting the lifestyle of Roman citizens. The estate encompasses 22 acres and contains elements of a heating system for the thermal paths, as well as for private apartments. One of the most famous art pieces in the villa is the Little Hunt. The mosaic depicts hunters using dogs and capturing a variety of game during their outing, including hare. The detail in the colors and characteristics of each character depicted in the mosaic is fascinating. 

What’s Included: breakfast, lunch, transfer, tour, accommodation

Day 5: A Brief History of Chocolate

In the morning, the town of Ragusa glows against the mountains. The layers of the city create a unique patter, separated by the New Town atop the hillside and the Old Town located on the quieter, narrow lower foothills. The splendid façade of the church of San Giorgio borders the edge of beautiful Piazza del Duomo. The Baroque structure stands at the top of wide, sweeping steps with three pillars flanking the doorway. The bell tower creates a tremendous skyline. You continue to the Baroque town of Modica. The beauty of the city is spread evenly along the charming cobbled lanes. Your guide leads you around corners, bringing you to elegant churches and opulent palaces. The city was restructured after an earthquake in the 17th century, bringing the elaborate Baroque style to the architecture during the rebuilding process.

Modica is also home to the centuries-old history of chocolate making in Sicily. Your guide leads you into an exquisite dolceria. The scent of indulgent dark chocolate fills as you enter. The store opened in the 19th century as a cake shop and has since balanced the traditions of the Arabian and Spanish art of sweets, along with the culture and passion of Sicily. You are guided into the backroom to learn the secrets of the store’s chocolate making, turning semi-ground cocoa into refined, contemporary edible masterpieces.

What’s Included: breakfast, lunch, dinner, tour, accommodation

Day 6: Where Modern and Ancient Life Mingle

The morning light washes over Castello di Donnafugata. The castle is perched on the hillside overlooking Ragusa and contains rooms draped in palatial elegance. Murals decorate the walls, and elaborate furnishings create a graceful and noble ambiance. After breakfast, your guide and transfer meet you at the hotel and lead you the timeless city of Syracuse. You can see the remnants of ancient life brushing against the whirlwind of the city’s contemporary lifestyle. Medieval lanes wind along the raised edges of the ramparts overlooking the shimmering Mediterranean Sea. Markets brim with fresh seafood and gregarious vendors. Your guide leads you to the Ear of Dionysius, an underground gallery nearly 197 feet long and 36 feet wide.

The opening to the grotto has a teardrop shape. Every whisper is amplified, echoing off of the limestone walls. The Legend states that Dionysius, the God of fertility and wine, built the cavern to eavesdrop on passersby. The mythical allure of the city’s rich ancient qualities only grows with each passing minute. The Eurialo Castle, which was erected in the 5th century BC, encompasses nearly four acres. The remaining stone walls lend credence to the legend of Archimedes. When the Romans besieged the city, Archimedes used a giant mirror to reflect the sunlight onto the Roman navy and set fire to their sails. The splendor of the story is as thrilling as you stand amongst the ruins.

What’s Included: breakfast, transfer, tour, accommodation

Day 7: Encircling the Peak

The 14th-century abbey known as Badia Vecchia has a Gothic style and fortress atmosphere emphasized by the battlements topping the building. After breakfast, your guide meets you at the hotel and escorts you to the foothill of the Mount Etna, the largest volcanic peak in Europe at an altitude of almost 11,000 feet. The summit looms over the colorful Baroque architecture of Catania. Lush vineyards and citrus orchards turn to rugged lunar landscape along the upper echelons of the mountain. You board the gondola connecting Rifugio Giovanni Sapienza, a clearing on the western slope at an altitude of 6,309 feet, to Torre del Filosofo at 9,580 feet above sea level.

The landscape is covered with millennia of volcanic ash, creating a lunar-like landscape of undulating gray hills and occasional rocks dotting the scenery. Your guide leads you closer to Cratere di Sud-Est, a perfect black cone that comes into view with steam rising from inside the crater. Each step forward to the active peak is thrilling; you can feel your heartbeat quicken. More steam puffs from the crater and drifts into the sky, mixing with the clouds. The rugged beauty of the area is captivating, embodying natural splendor and its raw power.   

What’s Included: breakfast, tour, accommodation

Day 8: The Edges of Mainland Italy

You look over the cliff of Taormina and see the tranquil island of Isola Bella protruding from the crystal clear turquoise sea. A narrow slit of sand connects the island to the shoreline, creating a perfect stretch of beach in the Bay of Naxos, radiant with white sand. At breakfast, you indulge in a refreshing espresso. After your guide meets you at the hotel, you venture to the bustling city of Messina and continue over the Strait of Messina to Reggio Calabria.

The city is unassuming and vibrant, filled with a unique blend of architecture symbolizing the Baroque and Neoclassical designs, inspired from a variety of societies. The cuisine is classically rustic, embodying the best of the mainland, with restaurants overlooking the Tyrrhenian and Ionian coasts. Your guide leads you to the incredible National Museum of Reggio Calabria, known as Southern Italy’s finest museum. The cavernous interior contains numerous Greek sculptures, including the Bronzi di Riace, two bronze statues discovered by a snorkeling chemist.

You have the unique experience of standing in the decontamination chamber before entering the bronze display to adhere to the microclimate and specially contained area. The larger of the two images stands more than six and a half feet tall, and was created in the 5th century BC. Standing in the vicinity of the statue is marvelous. You can look at the distinct features etched into the bronze, from the heroic figure to the focused gaze.  

What’s Included: breakfast, dinner, tour, accommodation

Day 9: Waving Farewell to the Sea

Outside of Taormina’s northern gate is the Arabian Necropolis. The marvelous archeological site was erected in the 10th century and contains symmetrical niches layered atop one another. The network of tunnels is believed to have traveled alongside the center of town, connecting the lower tiers of the Church of St. Peter outside the city walls. Taormina is filled with the luxury of a beautiful seaside and the majesty of a historical civilization. After breakfast, your private transfer meets you in the hotel lobby. On the way to the car, you listen one last time for the sea lapping against the base of the cliff. The breeze carries the semi-sweet aroma of the citrus groves in the Public Garden. You make your way to Catania-Fontanarossa Airport for your flight home.

What’s Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.