Day 1 – October 18
We will meet this morning to kick off our grand tour of Sicily in the glamorous hill town of Taormina, a long-time getaway for the world’s rich and famous. Here we will have a welcome toast at our meeting point with a view of the sea, and then head out to meet our local guide and learn about Taormina’s ancient, medieval, and modern history. This afternoon we’ll board our private coach and drive to our accommodations in the rich volcanic farmlands of north Mount Etna. A celebratory welcome dinner awaits. (Stay 3 nights near Mount Etna)

Day 2 – October 19
Today we’ll visit Randazzo, the center of the Etna wine region, to learn about traditional life in small town Sicily. This area has boomed in recent years, cultivating some of Europe’s hottest selling wines. A wine tasting will introduce the volcanic terroir to our palettes before visiting a local farm in the afternoon. A free afternoon, evening on your own, and an easy sense of la dolce vita will cap the day.

Day 3 – October 20
Mount Etna, hovering in the distance, is our focus today. We’ll drive to its north slope, through almond, pistachio, and orange groves, to climb the Piano Provenzana base camp and wintertime ski area. From here we’ll meet a geologist mountain guide and continue in 4×4 vehicles resembling moon rovers to the upper elevations of the mountain. Enjoy unforgettable views toward the Mediterranean Sea and a chance to hike “Mamma Etna” before we settle into a group lunch at a mountain hut.

Day 4 – October 21
This morning we head south making our way to the prestigious Benanti winery for a vineyard walk, cantina visit, and wine tasting lunch. After that we’ll continue to the ancient Greek city of Syracuse, where we’ll settle into a seaside hotel on the island of Ortygia. A Sicilian seafood group dinner awaits. (Stay 3 nights in Syracuse)

Day 5 – October 22
This morning we’ll begin peeling back the layers of history that is Siracusa. Our walking tour with a local guide begins at the vibrant Ortigia farmer’s market and continues with a boat tour around the harbor. Archimedes, Santa Lucia, and Caravaggio are a few of the characters that once animated this city, as thriving local artisans do today. With the afternoon free, you’ll wander the backstreets and make wonderful discoveries of local craft and creativity. The evening is free to explore the local dining scene.

Day 6 – October 23
Today we’ll take a day trip to the town of Noto with its stunning Baroque churches. We’ll tour its cathedral and fascinating parish churches, and enjoy a Sicilian granita at a streetside cafe. After free time for lunch and sightseeing, we venture to nearby beaches to taste the Mediterranean. A lively group dinner awaits back in Syracuse.

Day 7 – October 24
We will wave goodbye to idyllic Syracuse and drive north to the port city of Catania where we’ll meet our friends joining the tour for West Sicily. Together, we will visit the city’s main square and famous fish market, and tour the Museum of the Sicilian Landing of World War II. After, we’ll say arrivederci to our departing friends before road tripping through the interior hills toward the southern coastal city of Agrigento, where we’ll settle into rural accommodations and a group dinner together. (Stay near Agrigento 3 nights)

Day 8 – October 25
Today is devoted to Ancient Greek Sicily and the incredible Valley of the Temples at Agrigento. With the benefit of a local guide, we’ll wander past soaring temples, fallen statues, and ancient ruins overlooking the Mediterranean Sea. Then we’ll deep dive through Agrigento’s excellent archaeological museum to discover the amazing treasures unearthed here. This evening we’re back on the farm for dinner on your own at the farm’s restaurant.

Day 9 – October 26
Today is all about rural life in Sicily. We’ll take a tour of the farm, learn about the olive harvest and milling process, then begin a cooking class leading to lunch together. After a proper siesta, in the late afternoon we’ll head to a nearby beach town to dip our toes in the sea, an aperitivo, and dinner on our own. Join us for an optional fish dinner feast at a local seafood restaurant if you like.

Day 10 – October 27
Traveling north across beautiful green landscapes, we arrive in Segesta where we’ll visit one of the most beautiful ancient theaters in the world, still occasionally used today. We’ll continue toward the hilltown of Monreale and its Norman Cathedral above Palermo to experience the multicultural legacy of the Middle Ages in Sicily. We’ll peel back the stories, legends, and personalities that illuminated the church with our local guide, then descend into the bustling chaos of the city and check into our boutique hotel near the famous Ballaro’ Market. A welcome to Palermo group dinner awaits. (Stay 3 nights in Palermo)

Day 11 – October 28
This morning we meet our local guide, a scholar of women in Sicilian history, and tour the artistic treasures of the city, peeling back layers of culture from the Phoenicians, the Arabs, the Normans, and eventually the Italians. Palermo is a lively mix of Mediterranean cultures and the capital of Sicily. The afternoon and evening are yours to explore the many fascinating sights, or sit at a cafe and watch the world go by.

Day 12 – October 29
Palermo’s more recent history is a story of struggle against the mafia. With our local guide, we’ll venture into residential neighborhoods to learn how people have overcome its influence and brought new life and energy to the city. After a few hours of exploring the center in the afternoon, we’ll gather for a fun last night dinner together to celebrate our trip.

Day 13 – October 30
The tour is over after breakfast. We can help arrange private transportation to Palermo’s nearby airport.