Arrival
The closest major airport to Taormina is Catania-Fontanarossa Airport (CTA). It is located about 43 miles south of Taormina, a 1-hour drive or train ride away.

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 at Picciolo Etna Golf Resort & Spa)

Day 2 – October 19
Today we’ll visit Randazzo, the center of the Etna farming 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. We’ll then head to the prestigious I Custodi delle Vigne winery for a cantina tour and tasting lunch. An easy sense of la dolce vita will cap the day. (Free evening for dinner)

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, up to Piano Provenzana base camp and winter ski area. From here we’ll meet a geologist mountain guide and continue in 4×4 vehicles resembling moon rovers for a tour of the upper mountain. Enjoy unforgettable views toward the Mediterranean Sea and the option for a short hike among extinct craters before we settle into a group lunch at a rifugio mountain hut. (Free evening for dinner)

Day 4 – October 21
This morning we head south toward Catania to meet a local guide for a tour of the excellent Museum of the Sicilian Landing of WWII. Then we continue to the city’s main square to experience the local fish market with free time to enjoy a Sicilian street food lunch. We’ll regroup mid-afternoon and drive on 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 at Henry’s House Hotel)

Day 5 – October 22
This morning we’ll begin peeling back the amazing layers of history in Syracuse. Our local guide will take us through ancient temples, little backstreets, and past artisan workshops while telling stories of Archimedes, Santa Lucia, and Caravaggio. We’ll visit Ortygia’s outdoor market and discover its seasonal food and seafood scene. With a free afternoon and evening, you’ll explore the island and make wonderful discoveries of local craft and creativity.

Day 6 – October 23
Today we’ll take a day trip to the nearby town of Noto, famous for its stunning Baroque churches. We’ll tour its cathedral and fascinating parish churches, enjoy a Sicilian granita at a streetside cafe, and have free time for lunch. This afternoon and evening are free back in Syracuse.

Day 7 – October 24
We wave goodbye to idyllic Syracuse and continue our loop around Sicily. We’ll head inland to Ragusa Ibla to see its stunning cathedral, a Sicilian cart workshop, and a private palace, before having free time for lunch. This afternoon we’ll drive along the southeast coast to our next accommodation at an olive farm near the ancient city of Agrigento. We’ll enjoy a dinner together fresh from this season’s harvest. (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 an excellent local guide, we’ll tour the excellent archaeological museum before walking past soaring temples, fallen statues, and ruins overlooking the Mediterranean Sea. We’ll have a Slow Food lunch together in a nearby beach town. This afternoon will be free to relax at the farm and enjoy its restaurant for dinner.

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 in the kitchen learning to make local varieties of pasta. Of course we’ll then have lunch together from the fruits of our labor. After a proper siesta, we’ll explore the local area for an aperitivo and dinner on your own.

Day 10 – October 27
Traveling across rolling countryside animated with fall colors, we’ll arrive in Segesta where we’ll visit one of the most beautiful ancient theaters in the world, still used for performances 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 with an expert local guide. Then we 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. You are free this evening for dinner on your own.

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.

The primary airport serving the city is Palermo Falcone Borsellino Airport (PMO). Also referred to as Punta Raisi Airport, it is located about 22 miles northwest of the city center.