Sicily with Daniel & Caitlin Cutler

Benvenuti a Sicily! After settling in at our hotel, we’ll meet up with our tastemaker and convene for a round of cocktails and delightful welcome dinner. The meal—designed to introduce us to the core flavors of Sicily—is the perfect beginning of a journey filled with culinary delights, cultural discoveries, and moments of pure joy.

This morning, we’ll head to Agrigento. Alongside an expert guide, we’ll explore this former Greek colony was established in the 6th century BC and was a leading city-state in the Mediterranean world. Agrigento’s magnificent Doric temples dominate the ancient town, much of which still lies intact among acres of olive, pistachio, almond and fruit trees.

For lunch, we’ll ramble down the road for a special picnic. Hidden within the valley, the Kolymbethra Garden is dense with citrus trees, old olive groves and Mediterranean plants, its agricultural landscape sustained in part by ancient underground waterways. Once there, we’ll sit down for a private meal complete with freshly pressed citrus and other local specialties.

After, another side of rural Sicily comes into focus at a goat farm. We’ll meet a shepherd, learn about the work behind the island’s farmhouse cheeses and taste them where they are made. Later, dinner awaits back at the hotel.

Today, we make our way east along Sicily’s southern reaches toward the countryside near Ragusa. At a family-run organic farm, we’ll begin crafting our lunch well before anyone sits at the table. We walk the garden first, gathering seasonal vegetables and aromatic herbs before joining the kitchen to turn what is growing outside into a meal. Alongside the farm’s chef, recipes come through hands and memory with a little flour on the work surface, produce picked at its peak, the logic of cooking according to what the land provides.

After lunch, we’ll continue into Ragusa Ibla, rebuilt in elaborate Sicilian Baroque style after the devastating earthquake of 1693. Stone churches and palazzi climb the hillside, their carved façades catching the changing afternoon light. While there, we’ll step inside the workshop of a Sicilian cart artisan. Once practical transportation, these brightly painted carts became moving canvases crowded with saints, knights and scenes from Sicily’s storytelling culture. 

The day ends in the countryside near Ragusa, with dinner at our hotel.

We’ll take some time to relax at the hotel this morning before making our way to Modica—one of the island’s baroque gems. Once there, we’ll indulge in a pizza-making class led by our tastemaker, taking part in creating a dish the way it’s been crafted in Sicily since the 19th century. We’ll learn the traditional methods of stretching fresh dough into a thick crust, spreading a thin layer of sauce made from local tomatoes, and arranging cheese and other toppings that prioritize simplicity and fresh ingredients. And once they’re out of the oven, we’ll sit down to enjoy the fruits of our labor.

The rest of the afternoon is ours for wandering before we continue toward Scicli. There, the afternoon moves to the scents growing wild in the surrounding countryside. In a garden of aromatic plants, thyme and sage release their oils between the fingers while mint and citrus lend themselves to cocktails mixed from freshly gathered herbs.

As the light softens, aperitivo becomes dinner outdoors, with the garden supplying both the setting and part of the evening’s flavor.

After breakfast we’ll head out to visit majestic Mount Etna, an active volcano that towers almost 11,000 feet over the island — and occasionally glows red with lava! We’ll head to a local estate where heritage vines clamber up the volcano’s slopes to an altitude of over 3,000 feet, producing delicate whites and intense, fruit-forward rosés and reds.

Following our tasting, we’ll sit down for a wine-paired lunch before continuing up the mountain. Venturing up the slopes in a rugged jeep, the landscape shifts from fertile vineyards to lunar rock fields. With a guide leading the way, stops at various view points give way to smoking craters, sweeping views, and the raw power of one of Europe’s most active volcanoes.

Once back at ground level, we make our way to our hotel in Taormina to check in and have dinner on our own.

This morning we’re off to Taormina, pearl of the Mediterranean, to explore on foot starting with its ancient Greek amphitheater, overhanging the crashing surf below. From our perch at arguably the world’s most famous outdoor theater, the views of the bay of Giardini Naxos to the south, and mainland Italy to the north, are spectacular.

The afternoon is left open to spend our final day in Italy how you wish. Perhaps a long lunch, time along Corso Umberto, or a few quiet hours back at the hotel are on the agenda.

Later, our evening brings us to a family-owned villa overlooking the sea, a home passed through generations. In its kitchen, we cook together one last time, preparing Sicilian dishes before carrying them to the table. Wine is poured, plates begin making their way around, and dinner stretches into the evening on the terrace. After nearly a week of farms, kitchens, and shared tables, Sicily gives us a fitting farewell meal.

Arrivederci Sicilia! We’re off this morning after nine immersive days of adventure and culinary adventure. After breakfast, we’ll say ciao to each other, knowing the memory of our adventure together will live in our hearts forever! We’ll organize a group transfer to the airport for flights to mainland Italy and beyond.