Sicily with Tiffany Derry

Benvenuti a Sicily! Once we’ve settled into our hotel, we’ll gather with our Tastemaker for an evening of wine tasting and a welcoming dinner. Thoughtfully crafted to showcase the signature flavors of Sicily, this first meal sets the tone for a journey brimming with unforgettable cuisine, cultural immersion, and moments of awe.

After breakfast, we start our journey 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 venture up the slopes in a rugged jeep, the landscape shifting from fertile vineyards to lunar rock fields. With a naturalist guide leading the way, a short hike reveals smoking craters, sweeping views, and the raw power of one of Europe’s most active volcanoes.

After, we’ll head for a winery 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.

Then, we’ll indulge in a cooking class to make lunch under the benevolent eye of Le Mamme del Borgo, a collective of local grandmothers who will teach us how to knead the ancient flours into a supple pasta dough for maccarruni, a typical Sicilian pasta that’s traditionally rolled by hand and served in a wild boar sauce.

After, we’ll have a bit of downtown at our hotel before reconvening for dinner at a local spot.

In the late 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. 

But it’s not just the panorama we’re after—this small city is also known for its simple and stunning cuisine. As we weave through its cobblestoned streets and alleys, we’ll be treated an eclectic array of local favorites like involtini di pesce spada, a masterpiece of swordfish, breadcrumbs and local herbs.

Then for lunch, 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.

After that, the rest of the afternoon is yours to explore, and dinner is on your own. Whether you choose a cozy trattoria tucked into an alley or a cliffside restaurant with sweeping views, it’s bound to be a magical evening.

This morning, we’ll take some time to enjoy breakfast at our hotel before heading to Agrigento. 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.

We’ll drink in the sumptuous beauty of the gardens and ramble down the road for a special lunch. There, we’ll sit down for a picnic with a local shepherd, feasting on homemade ricotta and local pasta for lunch.

After arriving in Palermo and checking into our hotel, we’ll regroup for dinner at a gourmet restaurant. Perched above Palermo’s golden rooftops, we’ll feel like we’re dining in the sky on a three-level terrace with 360-degree views of the city center.  Alongside this panoramic vista, every bite carries the soul of Sicily, and every glance out reminds you just how far you’ve come.

Today, our first stop will be the iconic Salt Plains of Marsala. Here, we’ll explore the striking landscape of salt water pools divided by narrow strips of land, known as “la via del sale” or the Salt Road, where ancient Phoenician salt culture meets modern-day production methods, offering a glimpse into centuries-old traditions.

Continuing our exploration, we’ll indulge in a delightful visit to a local winery. Immerse yourself in the aroma of oak barrels and sample a selection of traditional Western Sicilian wines during a memorable tasting session. Afterward, we’ll enjoy a leisurely lunch at the winery, savoring the flavors of Sicily’s culinary heritage.

Next, we’ll journey to the medieval hilltop town of Erice, where we’ll treat our tastebuds to a pastry tasting, sampling delectable treats crafted with love and tradition. For dinner tonight, we’ll visit a local trattoria near our hotel and savor the best of local delicacies.

There’s no better introduction to freewheeling Palermo than the colorful Capo market; as we wander the stalls, listening to the singsong calls of vendors and inhaling an intoxicating swirl of aromas, we’ll be tantalized by the sharp tang of Sicilian citrus fruits, fragrant sesame-seed loaves pulled from a wood-fired oven, savory arancini (fried rice balls) and thick slices of sfincione topped with sweet tomato sauce.

Next, we’ll be treated to a historical tour as we take in Palermo’s stunning seafront, its terraces and courtyards a tapestry of hanging gardens perfumed with subtropical essence. Midday brings a hands-on pasta-making experience inside a private home, where we’ll roll, shape, and share a meal crafted from scratch. The afternoon is yours to wander or rest at your own pace before we meet up again for a lively seafood feast as the finale to our time in Italy. Alongside Tiffany and our new friends, we’ll toast to an incredible Sicilian experience!

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