Tour begins in Palermo at tour hotel at 3pm.

Day 1—As you drive into Palermo from the airport it hits you: domes, markets, decorated streets, palm trees, mountains, the sea, ships in the harbor, people and traffic everywhere. There’s something different about Sicily. Once checked into the hotel, we’ll gather for short introductions and head out to meet our local guide, a scholar of Sicilian history and culture, for a backstreets walk of hidden treasures and mystical fascination. Then we’ll celebrate the start of the tour with a group dinner, dining outside and enjoying the view. (Stay in Palermo 3 nights)

Day 2–Today we’ll head to the Monreale Cathedral above Palermo to experience one of the best works of the multicultural Middle Ages in Sicily. We’ll peel back the stories, legends, and personalities that illuminated the church with our local guide, then return to the city for an exhilarating walk through the amazing Ballaró food market, just in time for lunch on your own and a free afternoon. This evening we’ll regroup for an aperitivo and dinner in a private palace with descendants of Sicilian royalty.

Day 3–Palermo has twenty-eight centuries of history but today we’re going to focus on the most recent one, with a guided tour through modern neighborhoods following the fascinating lives of local residents. The afternoon and evening are free on your own to explore further, perhaps catch a show at the Palazzo Massimo opera house, and enjoy the city’s amazing food scene.

Day 4–We travel west today to visit the salt flats of Trapani and the Phoenician archaeological park of Mozia. Then it’s on toward Agrigento, where a countryside estate is our home for the next three nights and a group dinner awaits. (Stay near Agrigento 3 nights)

Day 5–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 olive trees overlooking the Mediterranean Sea. Then we’ll deep dive through Agrigento’s excellent archaeological museum. 

Day 6–With the coast not far, today we’ll relax and enjoy a la dolce vita day at the beach. But there will be drama–we’ll visit the incredible rock formation, the Scala dei Turchi, or Stairs of the Turks. Later this afternoon we’ll get to work with a pasta making cooking class and dinner together.

Day 7–We head inland this morning to the famous Villa Casale Romana. These are some of the best preserved ancient Roman mosaics in the world, featuring images of gods, animals, and the rituals of daily life. The day ends in the ancient Greek city of Siracusa with stroll around the idyllic island of Ortygia and a group dinner together. (Stay in Siracusa 3 nights)

Day 8–This morning we’ll begin peeling back the layers of history that is Siracusa. Our walking tour with a local guide will continue 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 craft and creativity.

Day 9–Today we’ll day trip to the Baroque towns of Southern Sicily. We’ll visit Ragusa and its stunning cathedral of San Giorgio and enjoy a Michelin star tasting lunch. In the afternoon we’ll explore Noto and its elegant streets and cafes. 

Day 10–After checking out of our new favorite hotel, we’ll drive north to Catania for the day. Exploring the center we’ll visit its famous fish market, climb to a rooftop view, and get a street food lunch. Then we’ll head to the old industrial district, repurposed as a cultural center and the excellent Museum of the Sicilian Landing of WWII. This evening we’ll stroll down the elegant main street of Taormina, perched between Mount Etna and the Sea. (Stay in Taormina 3 nights)

Day 11–With a local guide we’ll take a morning walk around Toarmina and make our way to its stunning ancient Greek & Roman theater, then a pizza making demonstration and lunch. With a free afternoon you’ll be able to head to the beach or hike in the hills above town.

Day 12–Mount Etna beckons as our grand finale. We’ll drive to its north slope, through almond, pistachio, and orange groves, and through ancient lava flows. With a geologist and mountain guide we’ll ride a gondola above the treeline to learn about Europe’s most active volcano. An elegant last night dinner awaits us in Taormina to celebrate our adventure through Sicily.

Day 13–The tour is over after breakfast. We can help arrange private transportation to Catania’s nearby airport. Or, continue the adventure on the Aeolian Islands extension. 

Day 13–The adventure continues by ferry to the Aeolian archipelago and the island of Salina, our home for three nights. The dramatic scenery here, of cliffs soaring above electric blue waters, has inspired myths and poets and dreamers alike. After a scenic drive around the island and a golden hour drink on our hotel terrace, we’ll settle into dinner with delicacies from the Sea.

Day 14–In the cool of the morning, we’ll head out early for an easy-breezy adventure around Salina. We’ll make our way to the village of Pollara, of Il Postino fame, with time to take a dip. This afternoon opt to explore the Santa Marina Salina harbor or take a rewarding hike in the hills with spectacular views. The evening is free for dinner on your own.

Day 15–Today we board a private boat and head for the remote islands of Filicudi and Alicudi. We’ll explore rocky coves, sea stacks, hidden grottos, and stunning volcanic geology. With provisions for a picnic, the adventure continues to find the perfect spot. Dinner together tonight will toast this timeless and stunningly beautiful place.

Day 16–Today we depart Salina and return to “mainland” Sicily. Ferry transportation to Milazzo is included. We’ll help you arrange transportation from there (Messina 30mins, Catania airport 2hrs, Palermo airport 2.5hrs). What a trip!

Aeolian Islands Extension
$1600 per traveler
$450 single room supplement

To book the Aeolian Islands, Book the Sicily tour above. We’ll send a special signup link in your Welcome Letter to add the extension.