Sicily and Its Isles

Itinerary

Day 1: 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.

Dinner

Day 2: 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.

Breakfast & Lunch

Day 3: 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.

Breakfast

Day 4: Trapani  - Marsala - Erice-Trapani

Discover the ancient craft of sea-salt harvesting during a guided visit to the salt pans of Trapani. Then continue to Marsala, heading down into a cellar for a taste of its renowned wine paired with traditional bites. This afternoon, journey to the enchanted hilltop village of Erice before returning to your hotel for dinner.

Breakfast & Dinner

Day 5: Trapani - Agrigento 

This morning, 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. Later this afternoon, wander through the imposing Greek ruins of the Valley of the Temples (UNESCO) in company of an expert guide.

Day 6: 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.

Breakfast & Dinner

Day 7: 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.

Breakfast & Dinner

Day 8: 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.

Breakfast & Dinner

Day 9: 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.

Day 10: 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.

Breakfast

Day 11: 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.

Breakfast

Day 12: 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.

Breakfast & Dinner

Day 13: Taormina - Tour Ends

Your journey through Sicily comes to a close today. Return home with memories of Italy’s favorite island.

Breakfast