Sicily & Naples with Jason Dady

Benvenuto a Sicily! We meet up with Jason and our fellow adventurers in historic Catania, then dive right into the epic market scene. We’ll sample some of Sicily’s finest street foods as fishmongers hawk fresh swordfish and octopus hauled in overnight. Afterwards, we head to nearby Siracusa, a seaside wonder basking in 2,700 years of history with deep Greek, Roman, Byzantine, North African and Norman influences.

Here, we’ll embark on a walking tour of the island of Ortigia, the bustling city center of Siracusa that still lives like a village—watch out for uneven cobblestones! Later we’ll join the locals on a passeggiata, or evening walk, on the promenade for an unforgettable first sunset together over the Mediterranean en route to an elegant and locally-sourced welcome dinner.

After a grand breakfast, we’ll be treated to a full-on exposé of traditional Sicilian cheeses at the CoRFiLaC Laboratory, where we find out how to taste cheese like pros and see all stages of the best Sicilian cheesemaking.

Next, we’ll move onto the next Sicilian ingredient: tomatoes. We’ll meet one of Italy’s most respected tomato growers, Casa Morana, where we’ll learn how they make epic tomato sauce and sit down to a picnic lunch on the farm.

Heading back to the hotel, we will stop at Noto, a breezy, walkable town, famed for its limestone Baroque buildings. Our afternoon pick-me-up? A fresh slice of hazelnut sponge cake and a cappuccino ghiacciato (iced coffee with almond milk granita) at a beloved family-run bakery.

Tonight, the dream-like lanes of Siracusa are yours to explore on your own.

After breakfast, we pack our things and move our Sicilian adventure to an active volcano over twice the size of Mt Vesuvius. At nearly 11,000 feet, Mt Etna is a towering green mountain that sometimes glows red. We’ll hike its craggy fissures with a local volcanologist who shares the ins and outs of Etna’s fascinating history.

Appetites worked up, we’ll move on to one of the area’s top-notch vineyards set atop the volcano’s slopes with panoramic views. At Tenuta San Michele, we’ll meet the winemaker, sip juicy reds and rich whites, then lunch on the best charcuterie and aged sun-dried tomatoes under the golden Sicilian sun. For the night, we’re sticking around Etna’s shadow. We set up in an intimate boutique hotel in a village at the volcano’s foot, where we can toast our day under a starlit sky.

Don’t sleep in today! Rise early for breakfast as the morning mist hangs over the volcano. Then pack up a sun hat, as we begin the day with a private boat ride along the breathtaking rocky shorelines and beaches of the Ionian Sea. It’s surreal scenery, as we see inside Grotta Azzurra, a sea cave with crystalline waters that glow blue. We enjoy a specially prepared lunch at sea, then dock to explore the lovely historic city of Taormina’s medieval lanes and churches, and its epic hilltop Greek theater with a full coastline panorama below.

We’ll have an afternoon full of Taormina’s endless appeal. Sit with an espresso in vibrant piazzas, browse shops in the alleys bursting with life, pop into a Gothic cathedral, and take some gelato to cliff-hugging terraces overlooking the sea. We’ll return to our hotel by the volcano for another star-lit night under Mt Etna’s gaze.

Our adventure of southern Italy moves on today, as we fly to a buzzing Mediterranean capital under the watch of Mt Vesuvius. We’ll jump right into Naples’ oldest spot for street food, Pignasecca Market. We’ll wander this outdoor mercato tasting fresh fruits and pastries, and dig into an Italian favorite, cuoppo Napoletano—because how else would you eat the best fried seafood than in a cone? We’ll then work off our treats on a walking tour of Piazza del Plebiscito in the city center, admiring Naples’ Royal Palace, Castle Nuovo and the immense Galleria Umberto. 

Naples is a blast after dark, and the evening is yours to explore its hipster bars with DJs spinning vinyl, and cozy intimate restaurants with wine lists as long as the night. Enjoy!

After breakfast we’ll find more of Naples’ storied appeal outside our door, and learn why Neapolitan pizza is not just to-go street food—it’s an art form, with a rich history dating back to the 1700s. The ‘modern’ pizza was invented here in 1889, when King Umberto I and Queen Margherita of Savoy visited Naples. The story goes that a local baker crafted a pizza in honor of the queen, with colors inspired by the Italian flag: red (tomatoes), white (mozzarella), and green (basil leaves)… and so the classic Neapolitan pizza was born! We’ll sit for an immersive, hands-on pizza making course with a wood-fired oven to craft different types of Neapolitan pizza, alongside Jason and a local pizzaiolo (pizza maker). Have your appetite ready.

But don’t get too full because our farewell dinner is a meal for the ages. After some rest and independent exploration, we’ll make our way to a restored cloister that has been transformed into a contemporary art gallery with cuisine run by Sabrina Russo, leader of the Food for Soul project. We’ll settle in for unforgettable courses and plenty of wine to toast our journey together. The night ends whenever it ends!

This morning, we’ll breakfast together and then say goodbye to Jason, pack up all we’ve collected, along with new memories, and head to the airport. Ciao!