Begin your stay in the heart of Palermo in the captivating old town, a heady alchemy of Norman, Moorish, and baroque architecture juxtaposed with street markets, dialects, and dishes molded by centuries of Arab influence. A morning tour on foot, bike, or Segway is the best way to appreciate the grandeur of the historic center—marvel at the 12-century Arab-Norman churches decorated with Byzantine mosaics, including the Royal Palace and Palatine Chapel. At lunchtime, sample the city’s street food on a food and market tour, or sign up for a cooking class and learn how to prepare traditional local dishes. Alternatively, architecture enthusiasts might visit nearby Monreale or Cefalù to check out the Norman cathedrals, among Sicily’s most significant cultural treasures and UNESCO World Heritage sites. 

Sicily was once part of the vast Greek empire known as the Magna Grecia, and vestiges of the Hellenic occupation are scattered across the island. Dedicate today to discovering some of Sicily’s most impressive archaeological ruins, and venture out to the Valley of the Temples outside Agrigento. Or, visit Segesta, closer to Palermo but no less dazzling. Both are home to surprisingly well preserved Greek temples dating from as far back as the fifth century BC. Go with a guide to better understand the history and architecture of these Doric treasures—some tours stop for a traditional Sicilian lunch in Agrigento or the hilltop town of Erice.

End your visit by exploring the Sicilian coastline by sea. Set sail along Mondello Beach to the picturesque marine reserves of Capo Gallo and Isola delle Femmine, stopping to swim in the crystalline waters and enjoy a lunch of Sicilian classics. Otherwise, sail around to the tip of Capo Mazzaforno to the west and the Finale di Pollina to the east. This stretch of coastline is known for its idyllic beaches, so take a dip in the turquoise bays along the route, before heading back to port to bid farewell to Palermo.