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 towns,  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 Michelin-star restaurant experience! 

The core of the itinerary has us based at Villa Aranjaya with the option to add to your itinerary before and after our stay at the Villa as follows: 

Wednesday, May 14 - Saturday, May 17, 2025: Palermo's Arab-Norman architecture, markets, churches and more; Monreale Cathedral; Agrigento and the Valley of the Temples; and the mosaics of the Villa Romana del Casale

Saturday, May 17 - Saturday, May 24, 2025: Villa Aranjaya with day trips that include the Infiorata flower art festival in Noto; the Sicilian Baroque towns of Ragusa, Modica, and Scicli; Siracusa's historic center; beach time in the Mediterranean; and the fishing village of Marzamemi

Saturday, May 24 - Monday, May 26, 2025: Wine-tasting paired farm-to-table lunch on the slopes of Mt. Etna; Taormina with its Greco-Roman amphitheater, fairytale like town with gracious buildings, sweeping views and phenomenal shopping, and its beautiful beaches.

Choose one, two, or all three!

Villa Aranjaya is a lovingly curated villa and farm located midway along Sicily’s eastern seaboard, offering the perfect vantage point for exploring some of Sicily’s most beautiful sights. 

Ensconced amid palm and citrus trees, the villa features 8 bedrooms all with en suite bathrooms, indoor and outdoor dining areas, living room, library, and a sitting room with views of Mt. Etna. 

Activities on site include pool, sauna, walking paths, tennis and volleyball courts, and table tennis. Oh, and it comes with its own staff and dedicated chef!