Sicily Guided Private Tours

Sicily Private Tours and Experiences Hosted by Local Experts

Sicily Guided Private Tours

Context Travel Sicily Tours

Sicily, an island with a history as rich and diverse as its landscapes, has been a crossroads of civilizations from the Greeks to the Normans, Arabs to the Bourbons. Known for its ancient ruins, intricate mosaics, and the imposing Mount Etna, Sicily's narrative is woven through its architecture, art, and cuisine. For curious travelers eager to delve into this storied land, our Sicily tours offer an unparalleled experience, connecting you with the island's past and present through the eyes of expert local guides, archaeologists, and historians.

If you're staying closer to Syracuse, start your trip with the Introduction to Syracuse Tour, where the Neapolis and the Duomo reveal Syracuse's ancient Greek heritage and its transformation through the centuries.

In Palermo, our Introduction to Palermo Tour uncovers the city's complex history, blending Arab, Norman, and Baroque influences in its architecture and urban layout. For food lovers, our Palermo Food Tour immerses you in Sicily's culinary traditions, showcasing the flavors that define Sicilian gastronomy in its bustling markets.

To explore one of Sicily's most iconic archaeological sites, join our Half-Day Agrigento Archaeology Tour at the Valley of the Temples, where you'll walk among the ruins of ancient Greek civilization.

If you're a fan of the hit HBO show White Lotus or simply love breathtaking vistas, our Introduction to Taormina Tour offers a picturesque journey through one of Sicily's most beautiful towns, with insights into its Greco-Roman past.

Nature enthusiasts can't miss our Full-Day Mount Etna Hiking Day Trip, combined with a Sicilian wine tasting, where you'll not only trek the slopes of Europe's highest active volcano but also savor the local wines shaped by its volcanic soil.

You can also try several of our newer experiences like the Introduction to Cefalù Tour introduces you to this charming coastal town, known for its Norman cathedral and serene beaches. In Catania, our Introduction to Catania blends historical exploration with the city's renowned street food culture. 

For those fascinated by antiquity, the Segesta Archaeological Site Tour and Selinunte Archeological Site Tour offer deep dives into these less-trodden yet significant Doric sites, providing a quiet reflection on Sicily's ancient history.

Our Sicily guided private tours are designed to cater to all levels of curiosity, offering personalized, in-depth experiences that go beyond the typical tourist path. Whether you're a history buff, a food lover, or an adventurer at heart, our expert guides are here to bring Sicily's multifaceted stories to life, ensuring your visit is as enlightening as it is unforgettable.
What Context Sicily Travelers Say
(4.9) 183 Reviews

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My family took a tour with Cetty the very first morning of our vacation in Palermo - an ideal way to set the stage for the days to come. She helped us to notice architecturally how converging cultures contributed robustly to this beautiful city, and adeptly put into context Palermo in its early days, as well as for how it continues to thrive today. Cetty connected with each member of our group of eight and really brought the city to brilliant life. This early experience with her set up our time in Palermo beautifully, and I would highly recommend this tour.
Cetty dug deeply with our small group and illuminated countless interesting facets about the Monreale Cathedral - this was an in-depth custom visit, and it was spectacular. Her depth and breadth of knowledge is staggering. The cathedral itself is dazzling, and she helped us see beyond the breathtaking visuals to understand more deeply how politics, power, religion and influence converge in this incredible space.
A wonderful immersion into markets, specialty shops, and history as we journeyed through Palermo. Cetty is a font of interesting information and personal connections that bring the city to life - for our eyes as well as our tastebuds. She gracefully kept our entire group of 9 engaged - no easy feat with ages of family members spanning 8 decades. She also made wonderful recommendations to visit artisans. I highly recommend this experience.
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