Itinerary

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.

   Accommodation: Hotel Porta Felice

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.

   Meals: Dinner
   Accommodation: I Mulini Resort

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. End your day at a medieval palace, where a countess guides you through her family’s home before pausing for an aperitif and hors d’oeuvres.

   Meals: Breakfast & Lunch
   Accommodation: I Mulini Resort

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. As the day draws to a close, settle into Trapani for two nights and watch the sunset fade against the crashing waves and whirling windmills.

   Meals: Breakfast
   Accommodation: Baia di Ulisse Hotel

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.

   Meals: Breakfast
   Accommodation: NH Collection Hotel

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.

   Meals: Breakfast, Dinner & Lunch
   Accommodation: NH Collection Hotel

7. Agrigento - Piazza Armerina - Taormina

   Venture deep into Sicily’s countryside to Piazza Armerina, home of the ancient Villa Romana del Casale (UNESCO), and explore the site with an expert insider for a locally guided tour of its impressive mosaics. In the afternoon, 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 before enjoying Sicilian food at dinner, surrounded by local musicians.

   Meals: Breakfast & Dinner
   Accommodation: NH Collection Hotel

8. 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.

   Meals: Breakfast
   Accommodation: Poggio del Sole Hotel

9. 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.

   Meals: Breakfast
   Accommodation: Poggio del Sole Hotel

10. Taormina - 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.

    Meals: Breakfast & Dinner
    Accommodation: Land's End Boutique Hotel

11. 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.

    Meals: Breakfast & Dinner
    Accommodation: Land's End Boutique Hotel

12. Ragusa - Pozzallo - Ferry to Malta - Three Cities - Sliema

    Grab your bags* and hop on a ferry** in Pozzallo. Say goodbye to Italy and venture to the island paradise of Malta, one of the smallest countries in the world. Start your exploration in Three Cities, a conglomeration of three fortified cities of medieval heritage. Once the setting of battles by the Knights of Malta, this area preserves endless layers of the past. Connect with the heart of the neighborhood at a Band Club, where locals gather to learn music and marching for the local festivals. Your day ends in Sliema, your home for the next three nights.

    Meals: Breakfast & Lunch
    Accommodation: Land's End Boutique Hotel

13. St. Julian’s - Valletta - St. Julian’s

    Your adventure continues in Valletta, the capital of Malta. Discover this fortified city on a guided walking tour. You’ll take in the picturesque Barrakka Gardens overlooking the harbor, featuring a charming blend of natural beauty and terraced arches. Then it’s your choice! Visit the private home of a modern-day Knight of Malta -OR- tour the masterpieces of Valletta’s Cathedral featuring Mattia Preti and Caravaggio. As the day draws to a close, enjoy a farewell dinner with your fellow travelers as you recount memories of the Mediterranean islands.

    Meals: Breakfast & Dinner

14. St. Julian’s - Tour Ends

    Say goodbye to Malta and the Mediterranean as your tour comes to a close today.

    Meals: Breakfast