Sicily with Caroline Schiff

Benvenuti a Sicily! After settling in at our hotel, we’ll meet up with Caroline and convene for a 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.

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 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 and then sit down to a family-style lunch

Following our lunch and tasting just when we think we’re too full, we’ll make room for granita—a uniquely Sicilian treat that somehow combines the best components of gelato, sorbet and sno-cones into one incredibly refreshing desert.

Then, we’ll indulge in a cooking class to make dinner 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.

Feeling fleet of foot? If so you’re invited out for a leisurely morning run with Caroline. If you’d rather sleep in, that’s certainly in the cards as well. 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.

After, we’ll convene again in the late afternoon for an informal aperitivo with Caroline at the hotel, and then dinner tonight is on your own.

We’ll head for Siracusa today, wending our way across the island to this 2,700-year-old seaside wonder that’s an intricate blend of Greek, Roman, Byzantine and North African influences.

Siracusa’s ancient heart is the island of Ortigia; we’ll dive in on a walking tour of its cobblestone alleyways — crowded with markets and temples, castles and churches, tucked around every corner. Then we’ll head to Tenuta Cavasecca for a visit to its olive groves and the ancient temple that now houses vats of freshly pressed oil as it rests after harvesting and milling. Finally, we’ll head to the ancient hall for a tasting of this liquid gold, followed by a family lunch straight from the garden.

Practically floating from lunch, we’ll settle in for a meandering road trip through the countryside. It’s a fine opportunity to catch up on sleep, a podcast or dive into the history of our next stop: Agrigento. As a long afternoon gives way to evening, we’ll arrive at our stunning countryside estate.

This morning is exquisitely slow. We’ll take some time to enjoy our hotel and its surrounding gardens, only readying ourselves for adventure by the late afternoon. At the golden hour, we’ll head 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 dinner. There, we’ll sit down for a picnic with a local shepeard, feasting on homemade ricotta and local pasta for lunch.

Dinner tonight is yours to embellish. 

Today, we lace up our boots and roll up our sleeves and step firmly into the world of Sicilian food and wine. Our day begins with a visit to a local winery for an enriching wine tasting experience, where you’ll sample exquisite Sicilian wines and gain insights into the winemaking process. Following this, we’ll partake in a hands-on cooking class, followed by a relaxed late lunch to savor the flavors of our creations.

The afternoon offers free time for personal exploration or relaxation. Dinner—whether at a local trattoria or within the serene ambiance of the hotel—is up to you.

As we bid farewell to our current haven and set our sights on Palermo, 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. As the day draws to a close, we’ll check into our hotel and prepare ourselves for beautiful Palermo tomorrow.

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. After a a few hours of independent exploration, we’ll meet up again for a truly magical farewell dinner. Alongside Caroline and our new friends, we’ll toast to an incredible Sicilian experience!

Arrivederci Sicilia! We’re off this morning after nine immersive days of adventure and culinary adventure. After breakfast we’ll say ciao to Caroline, and to each other, 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.