Fall 2026 Imagine Sicily Tour
October 14-24, 2026
Join us on a Sicilian adventure, full of authentic Sicilian tastes and experiences. Learn about Sicily’s complex history and enjoy unique experiences full of local color and traditions. We will explore some of Sicily’s treasured traditions, culture, and foods and wines, and meet new friends along the way. Come to know what makes the island so magical!
Join La RosaWorks on a Sicilian adventure, full of authentic Sicilian tastes and experiences.
Each year we add new visits and discoveries to this already favorite Sicily tour that visits the southeastern triangle of Sicily from Taormina to Noto and over to Agrigento. We will enjoy a cultural immersion, mixing the highlights along our route with off-the-beaten path excursions and experiences.
Sicily’s simply exceptional food and wine is always the protagonist, and we will sample a wide variety at fine dining establishments and rustic farms. We will meet old friends along the way and make new ones. Our team of expert and exceptional guides will engage us with talk about history, traditions, local culture, and anecdotes to amaze and delight. You will gain an understanding of the Island's evolution, historically one of the most sought-after on Earth.
- Recommended reading: “The Leopard” by Giuseppe Tomasi di Lampedusa
- Recommended listening: Karen La Rosa on the podcast “Exploring Sicily’s Val Di Noto”
- Recommended viewing: Inspector Montalbano written by Andrea Camilleri, on the MhZ Choice Network
Sicily’s southeast is beautiful, bountiful, and Baroque
This tour will fill quickly. Please tap below for reservation information.
Please contact me
with more information
about the Fall 2026 Imagine Sicily Tour.
Participation is limited.
Crystal clear waves lap at a seawall in Ortigia, Siracusa’s historical center.
A fun home-hosted lunch with a local chef!
Pizzolo is a delectable dish unique to the town of Sortino.
Greek drama played a significant role in Siracusa circa 5th century BC.
Beautiful handmade pottery has been important in Sicily for millennia.
Villa Romana del Casale contains some of the worlds most important mosaic floors
Photo credits: Karen La Rosa
Cost & Booking
To see the full itinerary and cost, please contact La RosaWorks for
We can make your arrangements for early tour arrival or late departure, or pre- or post-travel in Sicily at your request.
This itinerary is subject to minor changes and adjustments of equal or greater value..
For further information, please contact:
Karen La Rosa at
or call (646) 397-4175
Space is limited.
Please reserve your spot as soon as possible.
Please contact me
with more information
about the Fall 2026 Imagine Sicily Tour.
Travel Information
Information about passports, travel authorizations, driving in Sicily, and much more can be found on our detailed Sicily Travel Information page.
“But if I were asked to pick one constant, one quality that seems dependable, immutable, endlessly available, I’d say that it was intensity. For nothing in Sicily seems withheld, done half way, restrained or suppressed.”
- , Sicilian Odyssey
Photo credit: Karen La Rosa