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SIGNATURE MOMENT
Connecting with ​the​ Lampedusa family over a home-cooked meal
SIGNATURE MOMENT
Creating a traditional Sicilian meal​ yourself​ at our olive-grove inn
SIGNATURE MOMENT
Experiencing Ragusa’s magical evening light
SIGNATURE MOMENT
Seeing Caravaggio’s dramatic Burial of St. Lucy

Sicily: The Key to Italy

Nov 06-17, 2025

15 days | Italy | Literary Adventures

Readings:
  • The Leopard by Giuseppe Tomasi d​i​ Lampedusa
  • Selected poetry from Salvatore Quasimodo
  • Selected short stories from Maria Messina’s Behind Closed Doors: Her Father's House and Other Stories of Sicily
 
Palermo, in the words of journalist and native son Roberto Alajmo, is an onion — una cipolla. This city at the edge of Italy reveals its nature slowly. The same might be said for Sicily as a whole. For more than 10,000 years, layer upon layer has been added to the island’s history and culture by conquering warriors, merchants, sailors, and travellers from across Europe, North Africa, and the Mediterranean basin.

Our tour offers you the chance to explore many geographical regions of Sicily and experience its centuries of multicultural richness. At the same time, our leaders and guides will weave all threads into a coherent whole through carefully chosen readings, and time for discussion and reflection. As you peel back each layer of Alajmo’s onion, revel in the new delights that are uncovered — ancient Greek theatres still in use, golden Byzantine mosaics, sprawling Arab-Norman palazzi, vistas over an impossibly blue sea, the ruby red of a glass of nero d’avola.

You’ll start in Palermo, where the focus will be Giuseppe Tomasi de Lampedusa and his seminal novel The Leopard. You’ll also have time to explore Palermo’s revitalized art scene and taste its famous street food — the crowd-pleasing arancini (fried risotto balls) and pani ca’ meusa, a soft sesame roll filled with spleen, for those who don’t back down from a gustatory challenge.

It’s then time to leave the city behind for a few days at an agriturismo among the olive groves of the south coast. On excursions to nearby Agrigento, stand “with all Olympus before [you]” in the Valley of the Temples, the remains of a 6th-century BCE Greek colony. Zip back into modernity with Luigi Pirandello, whose radical works question the reliability of reality and the self.

More marvels of the ancient, medieval, and Renaissance worlds await at Syracuse. For British novelist Lawrence Durrell, Syracuse was “the whole of science, magic, total time,” where past and present coexist. Highlights are Caravaggio’s depiction of the burial of St. Lucy, housed in the Baroque church of the same name, the 2,500-year-old mikvah (Jewish ritual baths), and the archeological park that houses a Greek theatre where the tragedies of Aeschylus were performed before the playwright.

End your journey with an optional extension in the Mt. Etna area. This formidable volcano is also responsible for some of Sicily’s greatest pleasures, namely its beautiful, fragrant citrus fruit and distinctive wine grapes that grow in the rich soil. Toast your Sicilian adventure with a delicate nerello mesacalese or a savoury, salty carricante.

For the German polymath Johann Wolfgang Goethe, Sicily was the “clue to everything.” We’ll leave that for Italians to decide and instead invite you to join Classical Pursuits on a trip that will unlock Sicily’s boundless treasures. 
Literary Adventures Cultural Explorations Worldwide Explorers Club
Tour Cost (per person):
US$6995  Includes all taxes and gratuities.
Group Size:
12 - 16 participants

What’s included: Airport transfers on tour start and end dates; accommodations based on double occupancy in hotels listed or similar; ground transportation; all activities as described in the detailed itinerary; entrance fees; meals as specified in the detailed itinerary; clean water on the coach; literary discussions; books and readings; audio headsets for tours; gratuities for guides, driver, hotel staff, and included meals; all taxes; services of your Discussion Leader; fully escorted by our local English-speaking Tour Director

"Melanie and Georgio introduced us to a vast amount of historical, cultural, and literary information that this trip truly special." - Mike and Kelly S.
"I really enjoyed the literary tie in and also the breadth of ancient wonders in Sicily". - Classical Pursuits traveller on Sicily tour with Melanie in 2022
"I was impressed by the scope and depth of knowledge that Melanie shared with us as well as her patience and consistent effort to engage each of us in understanding, and appreciating new ideas. Truly unique". - Classical Pursuits traveller on Sicily tour with Melanie in 2022

Itinerary at a Glance

DayActivity
1Arrive Palermo
2Get to know Palermo on a street food tour
3Palermo and Il gattopardo (The Leopard)
4A day in the UNESCO World Heritage Site of Monreale
5Transfer to Mandranova on the Mediterranean coast
6Cooking class in Mandranova and Palma di Montechiaro
7Mandranova and the Valley of the Temples
8Transfer to Ragusa, with visit to Piazza Armerina
9Ragusa and wine tasting 
10The "stone garden" of Noto and Siracusa’s Parco Archeologico della Neapolis
11Walking tour in Siracusa
12Depart for Catania 
Optional Extension Taormina and the Mt. Etna area
Download Itinerary

Your Tour Leader

Melanie Blake is the executive director of Classical Pursuits and organizer of the annual Toronto Pursuits cultural salon. She studied English and French at Fordham University and the Université de Montpellier, and has an MA in literature and linguistics from the University of Nottingham. She loves languages, cocktails, and the unexpected.

Literary Adventures Cultural Explorations Worldwide Explorers Club
Tour Cost (per person):
US$6995  Includes all taxes and gratuities.
Group Size:
12 - 16 participants

What’s included: Airport transfers on tour start and end dates; accommodations based on double occupancy in hotels listed or similar; ground transportation; all activities as described in the detailed itinerary; entrance fees; meals as specified in the detailed itinerary; clean water on the coach; literary discussions; books and readings; audio headsets for tours; gratuities for guides, driver, hotel staff, and included meals; all taxes; services of your Discussion Leader; fully escorted by our local English-speaking Tour Director

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Sicily: The Key to Italy

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