discover Sicily like a local

The Sicilian Encounters Experience

With Sicilian Encounters, discover Sicily like a local as you’re introduced to the historic beauty, food, agriculture, and generous people of Sicily. We bring American friends together with our Sicilian family and friends. Immerse yourself in the rich culture, the delicious food, and the delightful wines.

Meet the Founder: Jen DeJong

A personal approach to travel in Sicily

Jen has 20+ years of travel coordination experience from previous jobs as a youth director, travel coordinator for Ministry Architects, and organizing service trips through churches and Illinois Women In Leadership.

She is the daughter of a Sicilian immigrant and still has many relatives in Sicily, including Uncle Liddu pictured here. Her love for Sicilian culture and international travel now can be shared with others who are ready to explore this beautiful island. Our private group trips include history, architecture, food and wine, leisure, and time with the locals. All-inclusive packages (meals, transfers, lodging, activities) are available as well as lodging and activities only packages.

All photos on this website were taken on a Sicilian Encounter, giving you an idea of the innate beauty that is so easy to capture. Your own Sicilian Encounter awaits.

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  • "Jen is very organized and brings a personal touch to the trip. It's so much more than what you get with a typical travel agency. You will see and experience the authentic Sicilian way of life."

    -Sara, Sicilian Encounters client

  • "I meet a lot of new people when I travel with other organizations. But this is the only trip where I walked away with new lifelong friends."

    -Jeff, Sicilian Encounters client

  • Jen was an amazing tour guide. Every day was planned accordingly with fun and educational. I enjoyed learning how to make ricotta cheese and hanging with the sheep. My all time favorite was hanging with her family and learning the history of their town.

    -Nakesha, Sicilian Encounters Client

  • "Jen is so knowledgeable about Sicily. She has the gift of allowing you to be immersed in the culture while you experience Sicily as more than a tourist. You become part of the Sicilian family."

    -Elaine, Sicilian Encounters client

  • “If you like to be immersed in culture and community, then this is for you. You’ll experience Sicily but more importantly you’ll experience being with the people, too.”

    -Bryant, Sicilian Encounters client

  • Jen will introduce you to the hidden gems of Sicily and some of the greatest food and hospitality you will ever experience. Jen LOVES Sicily, and you will too after being a part of the Sicilian Encounters family!

    -Mark, Sicilian Encounters client

  • Sicily through the efforts of Sicilian Encounters will bring you a sense of belonging, community - connectedness. Pasquale's Coffee Shop has become a happy place in my mind, somewhere I wish I could start the day every day.

    -Stephanie, Sicilian Encounters client

  • Jen shared the real Sicily with us. Each day, we experienced the culture, the people, the food, and the art of Sicily. Each experience exceeded my expectations and she always had extra surprises along the way. We all left with Sicily in our hearts.

    -Annette, Sicilian Encounters client

  • The Sicily trip was absolutely fabulous and so much better than I ever imagined! Jen told us it would be exciting and an “up close” experience with her family and other Sicilian people. The trip was touching and beautiful that resulted in memories to last a lifetime. I am now friends on social media with many of the beautiful people I met on this trip. Jen’s ‘down to the final detail’ trip itinerary was perfect and her Italian is pretty amazing too. I am planning to go back again with Jen soon!

    -Debbie, Sicilian Encounters client

  • A Sicily adventure with Jen is amazing. I've done it twice, and I would do it again. Jen arranges authentic Sicilian experiences that are not the run-of-the-mill tourist fare. Her style allows you to jump in and be part of relationships with Sicilians that she has been cultivating for years. Sicilians are so welcoming, generous, and fun.

    -Mike, Sicilian Encounters client

  • If you want to be immersed in the authentic Sicilian culture Sicilian Encounters is the one to trust. From family run and owned olive groves, local vineyards, so much delicious food to meeting people who treat you like long lost relatives, Jen will create an experience you will talk about for years to come. "

    -Susan, Sicilian Encounters client