Sicily & Naples with Ann Kim

Benvenuto a Sicily! We meet up with Ann 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. We’ll wander through ancient sites like the monumental (still in-use) Greek theater—built in a hillside for perfect acoustics over 2,000 years ago—and around dreamy Ortigia, the cobblestone island that still lives like a village. Later we’ll join the locals on a passeggiata, or evening walk, on the promenade for an unforgettable first sunset together over the Mediterranean.

After a grand breakfast, we explore nearby hill towns each as rewarding, and historic, as the next. First is Noto, breezy, walkable and famed for its limestone Baroque buildings. We’ll stop here at Caffe Sicilia for a fresh slice of hazelnut sponge cake and a cappuccino ghiacciato (iced coffee with almond milk granita) in a beloved family-run bakery. Afterwards we continue to Ragusa, an unreal mountain-top town with sloping alleyways and sun-kissed cathedrals. Here, we get 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 is a meet-up at 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. Then we stop in Modica to cap off lunch with something sweet, before returning to Siracusa to explore its lit-up lanes on our 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’ irresistible energy with a chef-led tour of its most famous creation: pizza! We’ll stop to savor slices at Naples’ most beloved pizzerias and learn the history of the world’s favorite pie.

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!

You hungry? This is our last full day, so expect to eat. 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. We’ll sit for an immersive, tasty “pizza course” with an authentic wood-fired oven to craft different types of Neapolitan pizza and hear some of Ann’s delicious insights. 

For decades, Naples has also been a bastion for new, cutting-edge art in a nation that often dwells farther back in time. On a guided street art and historical tour, we’ll explore Naples’ most creative expressions, vibrant piazzas, the grandiose Royal Palace, and more by foot—including Italy’s only known Bansky work. We also learn about Jorit, the local street artist gone global, and admire his San Gennaro mural that depicts the saint with the likeness of a local factory worker. Have your cameras ready!

For dinner, we’re the star guests at one of Naples’ top restaurants, Michelin-starred Palazzo Petrucci in Posillipo, where 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 say goodbye to Ann and the group. After breakfast, we’ll pack up all we’ve collected, along with new memories, and head to the airport. Ciao!