Enchanting Sicily 2026

Monday, May 19 to Sunday, June 1, 2025

Monday, May 25 to Sunday, June 7, 2026

14 days, 13 nights 

Arrive one or two days early for our optional pre-tour stay in Taormina!

On our signature tour of Sicily, you’ll discover off-the-beaten path towns, interact with locals, and immerse yourself in Sicilian culture and ancient history. You’ll tour intriguing UNESCO World Heritage sites, remote mountain towns, and charming seaside villages. You’ll attend a world-class performance of a classic Greek play in Siracusa’s Ancient Greek theater. You’ll amble through Palermo’s open-air markets and interact with Sicilians in a meaningful way. You’ll stay in 4-star hotels and characteristic inns and relish family-run trattorias as you explore Sicily’s 3,000 years of human history with authentic experiences, vibrant flavors, and sweet melodies that will capture your imagination.

About Our Signature May Tour…

Trip Highlights
  • Pre-stay option in Taormina (see itinerary below)
  • Professional, local guides
  • Siracusa/Ortigia*
  • Interaction with locals
  • Cooking class and market tour
  • Live performances of classic Greek theater and Sicilian folk music
  • Mount Etna*
  • Wine experience on Etna
  • Ragusa Ibla*
  • The Roman Villa of Casale in Piazza Armerina*
  • Valley of the Temples in Agrigento*
  • Hidden mountain towns
  • Palermo’s Arab Norman patrimony*
  • Off-the-beaten path seaside villages
  • Erice and Trapani’s salt flats
  • Coastal boat excursion
  • Outstanding seasonal cuisine
  • The logistics and details managed by our expert guides
  • Private and clean professional transportation

* UNESCO sites

$7,900 per person, double occupancy (Single Supplement $1,225). Land only. 
14 days, 13 nights. Includes everything but ten meals (all breakfasts, ten lunches, and five dinners, all transportation, all entrance fees and tickets, most tips.)

What people are saying…

Mark & Chris

“The trip vastly exceeded our already pretty high expectations. Each day exceeded the one before, with so many memorable experiences.”

Rating: 5 out of 5.

Gloria

“Thank you for those beautiful pictures, they will always hold great memories of the best people to be with.  We talk about this trip all the time.”

Rating: 5 out of 5.

Ed

“Allison, your commitment to give your clients the most for their money is inspiring. Also, your small group format helps create a bond within the group.”

Rating: 5 out of 5.