May 17 | Day 1: Overnight flight - You’re on your way to Sicily – an island paradise nestled amongst the deep blue waves of the Mediterranean. Look past the Italy you think you know and see how this coastal farmland balances ancient traditions and modern comforts.
May 18 | Day 2: Palermo, Italy - Tour begins. Start your journey in Palermo (UNESCO), Sicily’s welcoming capital city. Uncover the island’s deeply rooted heritage, teeming with Arab-Norman architectural masterpieces and delicate Classical designs. Come to know your fellow travelers over a welcome dinner.
May 19 | Day 3: Palermo - Begin your adventure tasting your way through Palermo’s lively markets on a walking tour unveiling the city’s historical center and introducing you to traditional Sicilian street food, which layers Oriental and Norman influences with local produce such as wild fennel, olives and spices. This afternoon, head to Monreale Cathedral, ascending on foot to see its majestic Byzantine mosaics. Then, it’s your choice! Explore the cathedral’s cloisters, taking in their serene atmosphere of the monastic complex -OR- ascend the southern tower to the panoramic terraces for a bird’s-eye view over Palermo.
May 20 | Day 4: Palermo - Impact Moment - Trapani - Experience an impact moment with Addiopizzo, an anti-Mafia nonprofit that supports locals who refuse to pay the Mafia’s protection fees. Visit Capaci, the site of a terrorist act led by the Mafia, and pay tribute to fallen activists. Chat with locals for a personal perspective and learn how they overcame the Mafia’s reign. Explore Trapani on a guided tour before settling into your hotel for two nights. This evening watch the sunset fade against the crashing waves and whirling windmills.
May 21 | Day 5: Trapani - Isle of Mozia - Marsala - Optional Excursion - Venture to the isle of Mozia, once a great trading port for the Phoenician, Greek and Roman civilizations. On the way, sail next to a submerged Roman road, once traversed on foot. Explore Mozia with a guide, visiting the ruins of its ancient port, and a museum featuring impressive Greek statuary. Then continue to Marsala, heading down into a cellar for a taste of its renowned wine. The remainder of the day is yours. Perhaps you will join an optional tour to Erice to visit Maria Grammatico’s famous bakery for a hands-on pastry-making class.
May 22 | Day 6: Trapani - Agrigento - Valley of the Temples - Agrigento - Begin in Mazara del Vallo, a humble fishermen city with ties to Tunisia. Head to an award-winning olive grove and learn about the Slow Food movement, which supports local cultures and preserves traditions. Try their unique olive oil at lunch before departing for Agrigento, where ancient roots and medieval buildings blend into modernity. Wander through the Valley of the Temples (UNESCO) with a guide at dusk.
May 23 | Day 7: Agrigento - Ragusa - Make your way to Ragusa (UNESCO), an ancient city perched upon a hill. Meander through its Baroque neighborhood with an expert guide, passing by winding lanes, cobblestone streets, and wrought iron balconies. Make the most of a free afternoon to explore on your own. As the sun sets, retreat to your countryside resort just outside the city.
May 24 | Day 8: Ragusa - Optional Excursion - The entire day is yours. With free time, you might choose to relax in the countryside and enjoy the resort’s amenities. Or, perhaps you will join an optional tour to the picture-perfect towns of Scicli and Modica, where you’ll enjoy a savory brunch at a ricotta farm before continuing to an Aztec chocolate shop for some sweet samples.
May 25 | Day 9: Ragusa - Milazzo - Ferry to Aeolian Islands - Isle of Salina - Lingua - Grab your bags* and hop on a ferry in Milazzo. Sail by Vulcano and Lipari on your way to Salina,** a far-flung isle surrounded by vibrant blue waters and dark volcanic rock. Somewhat off the beaten path, Salina is one of the less-traveled Aeolian Islands, preserved as a vacation getaway for Italians. Settle into the hamlet of Lingua for a 2-night stay.
May 26 | Day 10: Salina - Caper Farm - Optional Excursion - Dramatic landscapes of rocky cliffs and vibrant vineyards pass by on your way to nearby Pollara, famous for its traditional caper cultivation. Wander through the fields, tasting the salted flower buds accompanied by a glass of Malvasia, a locally produced dessert wine. The afternoon is yours to do as you please. Perhaps you’ll take an optional cruise to Stromboli, where you’ll swim off your private boat and dine at sunset; relax and watch for the signature glow of the island’s active volcano.
May 27 | Day 11: Salina - Ferry to Milazzo - Taormina - After a relaxing morning, ferry back to mainland Sicilia. Journey along the Ionian Coast to Taormina, a seaside hub of ancient Greek theaters and hilly walkways. Settle into your new home for the next three nights and enjoy a free evening to explore on your own.
May 28 | Day 12: Taormina - Discover Taormina with a local guide, leading you to the city’s Duomo, public gardens, and the well-preserved Greek theater. Walk in the footsteps of ancient attendees and take in an unparalleled viewpoint of the adjacent ocean. Spend the afternoon on your own. Perhaps you’ll grab a bite to eat at a sidewalk café, or peruse the local boutiques for handcrafted souvenirs.
May 29 | Day 13: Taormina - Mount Etna - Taormina - See Sicily’s wilder side on an off-road adventure to Mount Etna. Stare up at the iconic peak as your vehicle climbs along the sides of Europe’s largest active volcano. Spend the day exploring this legendary giant, passing by lava formations and basalt rocks. This evening, toast to your Sicilian sojourn at dinner, surrounded by local musicians.
May 30 | Day 14: Taormina - Tour Ends - Your journey through Sicily comes to a close today. Return home with memories of Italy’s favorite island.