Sicily, the largest Mediterranean island, is just off the "toe" of Italy's "boot." Originator of the cannoli, Sicily is also the 3rd largest producer of wine in Italy and boasts Mt. Etna, the tallest active volcano in Europe. Due to its strategic location, Sicily has been inhabited over the years by Greeks, Romans, Germans, Byzantines, Arabs, Normans, and Spanish. This rich and varied history is reflected in its architecture, language, culture, and food. 

Our itinerary is designed to have you experience the best that Sicily has to offer, explored through a combination of group outings and time on your own.  From beautiful beaches to resplendent cathedrals, magnificent Greek temples, gorgeous Baroque palaces, and picturesque hilltop castles,  Sicily is a treasure trove for the senses. Many of the places we’ll visit are UNESCO World Heritage sites, local favorites, or off-the-beaten path gems. Along the way, we’ll sample local foods and wines, and even indulge in a couple of Michelin-star restaurant experiences! 

Arrival in Palermo and transfer from the airport to our hotel. Welcome dinner. Overnight in Palermo’s historic district.  

This morning explore Palermo’s vibrant outdoor markets, then in the afternoon we’ll enjoy a walking tour of Palermo’s Arab-Norman architectural highlights. Evening at leisure. Overnight in Palermo. 

Morning at leisure to explore more of Palermo’s cultural offerings. Afternoon outing to the seaside town of Cefalu`, known for its beautiful beach and UNESCO listed cathedral. Lunch and dinner on your own so you can explore this town as you please. We'll return to Palermo after dinner.  

Take off this morning to visit the UNESCO listed Monreale Cathedral, filled with brilliant gold Byzantine mosaics, then the fairytale town of Erice, with castles perched high atop cliffs. That night we’ll stay in the seaside town of Trapani on Sicily’s western shore.  

Mid-morning we’ll depart for a vineyard tour near the town of Marsala. There we’ll enjoy a wine and marsala tasting lunch before heading on to Agrigento, where we’ll be staying overnight near the Valley of the Temples.  

This morning we’ll tour the UNESCO listed Valley of the Temples, some of the best-preserved Greek temples in the world. Afternoon at leisure to further explore the valley and neighboring botanical garden, or head to the beach that’s walking distance from our hotel. Overnight in Agrigento.  

Today, we pass from Sicily’s Greek roots to its Roman past with a tour of the UNESCO listed 4th c. Villa Romana del Casale, which contains a breathtaking collection of mosaics in their original setting. Following lunch, we’ll head to southeast Sicily to explore the Baroque town of Noto. Overnight outside Noto. 

Day trip to soak in the UNESCO listed Baroque churches and palaces of Ragusa and Modica. Enjoy a guided walking tour in Ragusa, followed by a 2-star Michelin lunch. In Modica, we’ll visit one of its famous chocolate houses that still produces artisanal chocolates according to ancient recipes and methods, then leave you free time to explore. Overnight outside Noto. 

Today we’ll depart Noto, but not before stopping to take in “L’Infiorata”, the annual festival that turns one entire street in town into an avenue of flower art created by teams from around the world! En route to Taormina, we’ll stop for a vineyard tour, wine tasting and local production lunch at the base of Mt. Etna. Overnight in Taormina. 

Climb up this morning to visit the Greco-Roman amphitheater from the 3rd century B.C., with sweeping views down Sicily’s eastern coast to Mt. Etna, then midday, we’ll celebrate over a Michelin 1-star farewell lunch. Spend the afternoon and evening exploring the beautiful seaside town of Taormina at your own pace and on your own terms. Overnight in Taormina. 

Today we’ll say goodbye to Sicily with a transfer to Catania for flights back to the Italian mainland, the States, or elsewhere in Europe!