A distinct and indefinable island, Sicily has withstood centuries of tyranny and cataclysm to emerge as a vital and varied cultural region. The Mediterranean's largest island, Sicily's soil and architecture reveal layer after layer of intriguing history and rule by Arabs, Greeks, Romans, Saracens, French, Spanish, and Bourbons. Home to some of the finest examples of Greek architecture in the world, Sicily is an archaeologist’s paradise.

A lush green spectacle in springtime and a vast golden stage in autumn, this itinerary pedals the south and northeast tip of the island to areas overlooked by the tourist masses.

Day 1: Caltagirone

We start our ride in the beautiful old town of Caltagirone. Settled by the Greeks, Caltagirone is known for its azulejos (Spanish style glazed tiles). Explore the mansions and spacious squares of this charming town, and climb La Scala, the magnificent stairway as you become accustomed to the Sicilian way of life.

Day 2–3: Ragusa and loop to Donnafugata

Day 2: Ragusa is a city in which urban expansion, fortunately, has not ruined the character of its 18th century neighborhoods. In the afternoon, we’ll visit the fascinating Ragusa Ibla, a vestige of the Baroque period.

Day 3: Ride to the beautiful Villa Donnafugata, the rural summer vacation estate of the Arezzo family, and explore the valley of the Irminio River canyon before returning to Ragusa for a walking tour.

Day 4: Siracusa

Discover Siracusa, one of the most important Greek colonies in the area, and a cultural and political center for thousands of years. Visit an archaeological sites and dine at a typical Sicilian restaurant.

Day 5: San Giovanni la Punta

Bike in one of Sicily's most fascinating archeological reserves and nature sites before arriving at the slopes of Mt. Etna to prep for our next day hike.

Day 6: Mt. Etna and Arrivederci!

On your final day, shuttle and hike up Mt. Etna to see the volcano and absorb the magnificent views. After the hike, we'll provide one group shuttle to the Catania airport, where you can make connections. We're happy to assist you with any further travel plans!