8-Nights Enchanting Sicily from $7,199

Itinerary Details

Day 1: Welcome to Palermo

On arrival at the airport, you'll be warmly greeted and chauffeured to your 5-star hotel. The balance of this day is yours to relax and get settled, or to explore at your own pace.

Day 2: A Taste of Palermo #WHS#

Meet your personal guide at the Teatro Massimo, one of the largest opera houses in all of Europe. Set on the Piazza Verdi, it's the perfect starting point for your private walking tour, designed to immerse you in the world of Sicilian street food. Stroll with your guide as they share insight into Palermo's rich history and the many civilizations that ruled here across the ages. Arriving at the lively Mercato del Capo, you'll join local residents as they go about their daily shopping, pausing at various vendor stalls to sample some local fare—from Arancini (stuffed rice balls) and Sfincione (Sicilian-style pizza) to Panelle (chick pea fritters). A short walk from the market, you'll discover the Cathedral of Palermo: Built by the Normans in 1184 on the site of an Islamic mosque that was previously built over an ancient Christian basilica, it's a fascinating illustration of Palermo's many-layered history. Continue to the lovely Piazza Bellini to visit a 12th-century church and the Santa Caterina Monastery, famed for its lavish Baroque style. End your tour with a traditional Sicilian dessert, perhaps a Cannolo Siciliano or a slice of Cassata Siciliana, a sponge cake traditionally made with ricotta cheese, candied fruit and marzipan. After sightseeing, the balance of this day is free to enjoy and explore as you wish. This evening, you'll enjoy a delightful 4-course dinner at Buatta Cucina Popolana, a charming restaurant known for its fine presentation of traditional Sicilian cuisine. Meals B+D

Day 3: Travel to Monreale + Agrigento

Departing Palermo this morning with your personal car and driver, you'll travel to Monreale to visit one of the island's most important sites. Dating back to the 12th century, the Monreale Cathedral #WHS# is heralded for its harmonious blend of Arab, Byzantine and Norman elements framed by traditional Romanesque architecture; inside, you'll discover beautiful mosaics, some of the most impressive in all of southern Italy! Then continue your journey to an enchanting wine estate in the Sicilian countryside. Learn about the various vines that have been cultivated here for generations including Nero d'Avola, perhaps Sicily's most important red wine grape, and Inzolia, a white wine grape used to produce Marsala wines. Enjoy a tasting of their fine vintages paired with traditional Sicilian snacks. Your day ends in Agrigento where you'll check in to your 5-star hotel. Meals B

Day 4: The Valley of Temples + Onward to Siracusa

This morning's private tour through the Valley of the Temples #WHS# weaves together a tapestry of ancient history and archaeology. Founded as a Greek colony in the 6th-century BCE, Agrigento, then known as Akragas, swiftly rose to prominence as one of the Mediterranean's greatest cities of antiquity. Today, its famed Valley of the Temples stands as a testament to its ancient grandeur and the architectural style of Greece's Archaic Period, a time of burgeoning city-states and cultural consolidation across the Mediterranean. Among these ancient remnants of sanctuaries, tombs, and majestic city portals, the Temple of Concordia erected in 420 BCE is remarkably intact and sure to be a highlight of your exploration. After a break for lunch on your own, travel onward to the charming hilltop town of Piazza Armerina to visit the spectacular Villa del Casale #WHS#. Built by a wealthy Roman merchant in the 2nd century, these ancient villa ruins feature finely preserved mosaics. Among the best in the world, they depict characters from Roman mythology and scenes of ancient life—in such precise detail that you will be able to identify everyday objects, plants and animals. End your day in the coastal town of Siracusa, where you'll check in to your 5-star hotel. Meals B

Day 5: Tailor Your Day in Siracusa #WHS#

Known as Ortigia, the historical center of Siracusa is set on a small island connected to the rest of the city by a charming bridge erected in the 19th century. Filled with lovely Baroque architecture, the old town is pedestrian friendly and a delight to explore at your own pace. To enhance your day, we invite you to choose one of these included excursions. Meals B Siracusa Walking Tour: Founded by Greek settlers from Corinth, Siracusa quickly rose to prominence as the foremost city in Magna Graecia. Your expert private guide will bring this ancient grandeur to life as you explore important sites at the Neapolis Archaeological Park, including the Greek theater, Roman Amphitheater and mysterious Ear of Dionysius—a cavern with perfect acoustics. Continue to the nearby island of Ortigia to explore Siracusa's old town in the company of your expert guide. Learn about its ornate Baroque landmarks and stroll along winding streets lined with artisanal workshops. Tour Duration: 4 Hours Private Morning 2-Hour Boat Tour: With its impressive waterfront of picturesque buildings set directly above the sea, the vistas of Siracusa and the island of Ortigia from the water are stunning! Cruising in your privately chartered motor boat, you'll also explore farther along the coastline to take in the region's natural splendor, a land of rocky coves and rugged grottoes. Weather and sea conditions permitting, you might stop for a swim before enjoying fresh fruit and prosecco as you head back to port. Tour Duration: 2 Hours Private Sunset + Aperitif Boat Tour: Like the morning cruise, this excursion promises a spectacular view of Siracusa, Ortigia and the enchanting coastal landscapes. Setting out from port as the sun begins its descent toward the horizon promises the added delight of witnessing these scenes in the softer light of sunset. Sicilian appetizers and some local wine enhance this memorable experience. Tour Duration: 2 Hours

Day 6: A Free Day in Siracusa

Take advantage of our hotel's city-central location to explore more of Siracusa at your own pace. Meals B

Day 7: Chauffeured Journey to Taormina

Sit back and enjoy the scenic 90-minute drive northward along Sicily's eastern coast. Arriving in Taormina, enjoy a privately guided walking tour in a town that has become synonymous with style and elegance. Tracing its history to ancient times, Taormina became a fashionable resort in the 19th century, popular with European aristocracy. Wander along cobblestone streets lined with inviting cafes and boutiques, and visit the ancient theater, built by the Greeks in the 3rd century BCE and later refurbished by the Romans during their rule over the island. Once a dramatic stage for Greek tragedies, the wondrously preserved theater now hosts festivals and special events against its spectacular coastal backdrop. After your guided tour, take some time to explore Corso Umberto, the lively street that runs through town. Relax at one of the quaint cafes, indulging in a gelato or sipping almond-flavored wine, a unique local specialty. Enjoy a delightful 2-night stay at your 5-star hotel here in Taormina. Meals B

Day 8: Delight in a Day at Leisure

This entire day is yours to enjoy the myriad charms of Taormina, set dramatically on verdant hills that rise steeply from the blue waters of the Mediterranean. Meals B

Day 9: Depart Sicily

We include your chauffeured transfer today to Vincenzo Bellini Catania Airport for your onward or homeward journey. Meals B