A Remarkable Window into the Past...

With a recorded history that goes back to the Phoenicians in 750 BC, Sicily has been at the crossroads of the western world since antiquity. One after the other, successive empires have fought for and conquered the strategically situated island--the Greeks, the Romans, the Normans, the Lombards--with each successive regime constructing a network of fortresses to subdue the inhabitants and solidify it's hold upon the territory. Sicily is not just a sojourn, it's an adventure that offers a remarkable window into the past...

The Inaugural Departure

Castles at the Crossroads will depart for the first time on May 26, 2023 from Palermo, Sicily, and conclude on June 3 in Catania, Sicily. This panoramic, 9-day itinerary (view the sojourn map) takes you entirely around Sicily to explore over 2,500 years of its fascinating history, with visits to its most significant castles, fortresses, and other stunning historic landmarks, including: 

  • Palazzo Reale 
  • Palazzo della Cuba
  • Arab-Norman Palermo and the Cathedral Churches of Cefalù and Monreale, a UNESCO World Heritage Site
  • The Archaeological Park of Segesta
  • Castello di Venere
  • The mountain-top city of Erice
  • The Archaeological Area of Agrigento, a UNESCO World Heritage Site
  • Lombardia Castle
  • Villa Romana del Casale, a UNESCO World Heritage Site
  • Milazzo Castle
  • Ursino Castle
Travel with a Renowned Expert
Sojourn Leader: Paul Martin Remfry

This fascinating travel program is led by Paul Martin Remfry, one of the greatest castle scholars of our era. A meticulous researcher, Remfry has spent over 30 years studying medieval history, genealogy, and architecture and has authored over 50 books and scholarly papers on medieval castles, abbeys, and battles.

Experience Extraordinary Sicily
Food, Wine, and Stunning Cities...

Along the way, we will immerse ourselves in Sicily's celebrated culinary tradition, enjoying spectacular meals, wine tastings, and even a special sampling of Sicilian pastries. 

You will also enjoy overnight stays in several of Sicily's most coveted and scenic locations, including:

  • Trapani: 2 nights
  • Agrigento: 1 night
  • Enna: 2 nights
  • Cefalù: 1 night
  • Taormina: 2 nights