Sicily: Palermo to Taormina

Ciao and welcome to Sicily! Palermo is the region’s capital and cultural epicenter, with Arab, Norman, and Baroque influences that create a feast for the senses. Get settled into our stylish hotel before a Group Meeting at 6:00 PM, followed by an included Welcome Dinner.

Included meals: Dinner

Buongiorno (good morning), Palermo! Today begins with a playful ride through the old town aboard a vintage 3-wheeled Ape Calessino. Afterward, we’ll continue exploring on foot, tracing the layers of Moorish, Norman, and Baroque influence that have shaped the city for centuries. We’ll stand before the 4 fountains of the Quattro Canti, wander the grounds near Palermo’s grand Cathedral, and lose ourselves in the narrow lanes of the historic center. For lunch, we’ll head into the Ballarò and Vucciria markets, where sizzling street food stalls create a world all their own. We’ll sample the city’s essential bites, crunchy panelle and cazzilli, warm arancine, and sweet cannoli, prepared just as generations of Palermitani have always made them. This afternoon, we’re free to shop, explore, or relax.

Included meals: Breakfast, Light Street Food Tasting

Today, we trade city streets for the rolling countryside, arriving at an elegant family estate for a wine tasting rooted in generations of tradition. We’ll indulge in their signature Syrah, alongside native Sicilian varietals like Grillo, Inzolia, and Nero d’Avola, sampling our way through what makes this terroir so special, before sitting down for a delicious lunch. From there, we’ll wind our way to Monreale, a hillside town just beyond the city, to marvel at the Monreale Cathedral, a 12th-century Norman masterpiece renowned for its golden mosaics depicting biblical scenes in astonishing detail. We’ll wander through the adjoining cloister before wrapping up the day. Back in Palermo, we’ll have the evening at our leisure.

Included meals: Breakfast, Lunch

After breakfast, we’re off to dabble in 2 very different worlds, starting high above the coast in Erice, where medieval stone streets and ancient legend intertwine in a town famed for having around a hundred churches. We’ll explore the Cyclopean Elymian-Punic walls and the atmospheric Castle of Venus, browse the work of local artisans, and stop for a sweet indulgence at Maria Grammatico’s bakery, a beloved institution. From there, we’ll descend toward the sea to visit western Sicily’s striking salt pans, where age-old evaporation techniques once extracted salt from seawater and where the surrounding wetlands now shelter a wide variety of bird species, all set against a backdrop of historic windmills. We’ll stop for lunch before exploring the mills, then continue onward to our hotel in Mazara del Vallo, where we’ll have some free time before an included dinner at the hotel.

Included meals: Breakfast, Lunch, Dinner

Today takes us deep into the Sicilian hinterland for one of the island’s most genuine adventures, an exploration of the Val di Kam and the village of Caltabellotta, a hidden gem once known as Triocala. We’ll enter through the evocative Pirtusu, a natural stone gateway that frames the epic views of terracotta rooftops and the Verdura River valley, before wandering the village’s maze-like alleys. We’ll visit the town’s Cathedral and its smattering of historic churches, pausing at open workshop doors where local artisans still practice trades passed down through generations. We’ll round out our visit with a tasting of local pecorino cheese and a traditional Sicilian lunch, savoring the authentic flavors of this beautifully preserved corner of the island. Later, we’ll return to Mazara del Vallo and have the remainder of the day free.

Included meals: Breakfast, Lunch

Today marks one of the true highlights of our Sicilian journey, as we head to Agrigento to explore the Valley of the Temples, a UNESCO World Heritage Site and one of the best-preserved remnants of Greek civilization anywhere in the world. Wandering among temples that have stood for over 2,500 years, including the remarkably intact Temple of Concordia, we’ll take in a landscape where golden hills, deep blue skies, and ancient ruins come together. From there, we’ll be hosted in a citrus grove for a super-exclusive, private lunch amid trees planted by Cistercian monks in 1740. Afterward, we’ll continue on to Noto, where we’ll check in, then head out for dinner in the city known for being southern Italy’s burgeoning LGBTQ+ hub.

Included meals: Breakfast, Lunch, Dinner

Rise and shine! Today brings us face to face with Sicily’s Greek, Roman, and Baroque legacies, starting in Ortigia, the historic heart of Siracusa. We’ll visit the mythical Fountain of Arethusa, then explore winding lanes where ancient temples meet medieval fortresses and Baroque churches before stepping into the Cathedral of Siracusa, built atop the Temple of Athena. We’ll break for lunch at a contemporary restaurant featuring seasonal Sicilian cooking before heading to Noto, a city reborn in Baroque splendor after the 1693 earthquake. We’ll take in landmarks like Palazzo Ducezio, Palazzo Vescovile, and the Church of San Domenico, before closing out the day with a sweet Sicilian tradition: a granita and warm brioche at one of Noto’s classic bars.

Included meals: Breakfast, Lunch

After breakfast, we’ll set off northward, stopping in the village of Motta Camastra to meet a group of local ‘nonnas’ who will guide us through a cooking class using generations-old recipes before we chow down on our creations. From there, we’ll wander through Savoca, a peaceful hill town lined with cobbled streets and scenic, film-famous viewpoints. Notably, Francis Ford Coppola filmed parts of The Godfather here. We’ll end the day in Taormina, the world-renowned ‘Pearl of the Mediterranean,’ exploring its crown jewel, the Ancient Greek Theater, a 3rd-century-BC site that once welcomed up to 5,000 spectators and today offers unforgettable views of Giardini Naxos, Mount Etna, and the Calabrian coastline. With a local guide leading the way, we’ll spend our remaining time wandering Taormina’s elegant streets and blooming balconies.

Included meals: Breakfast, Lunch

We love to end our trips on a high note, and today, we’re taking that literally as we set out to discover the raw power and beauty of towering Mount Etna! Riding in rugged jeeps with naturalist guides, we’ll explore a UNESCO World Heritage landscape shaped by more than 400 craters. From dramatic vistas to quiet, untouched trails, Etna offers a side of Sicily few ever get to see up close. Our journey continues at a winery perched high on the volcano’s slopes, where we’ll stroll through the vineyard, taste Buonora, Tefra, and Ghiaia Nera wines alongside a spread of local cheeses and cured meats, and enjoy a lunch inspired by Etna’s culinary traditions. Later, we’ll return to town and gather for our Farewell Dinner at a garden oasis in Taormina filled with citrus trees, palms, and the fragrance of wisteria. As we raise a final glass together, we’ll reflect on the wonderful memories we’ve made and the extraordinary piece of the island that we’ll carry in our hearts forever.

Included meals: Breakfast, Lunch, Dinner

After breakfast, enjoy a complimentary transfer to the airport. Safe travels home, and thanks for joining us in Sicily!

Included meals: Breakfast