Jessica

Travel Advisor

I grew up in the mountains of Central Oregon, but Italy was always part of my story. My great-grandparents emigrated from Puglia and Sicily, and I grew up hearing about my dad’s time living in Florence. I couldn't wait to discovery the country that shaped my family. 

At nineteen, I moved to Florence to work as an Au Pair (nanny). It was my first time in Italy, and it confirmed what I had sensed for years: this was a place I wanted to understand beyond a short visit. In my late twenties, I obtained dual Italian citizenship and returned to live in Florence for a year and a half. Living there gave me a practical understanding of daily Italian life that continues to shape how I approach travel planning today.

As a Travel Advisor with Italy With Bella, I design custom itineraries that are thoughtful, well-paced, and tailored to each client’s goals. I handle hotel selection, private transfers, curated experiences, restaurant reservations, and the many small details that make a trip feel seamless.

I pay close attention to logistics and flow. The spacing between destinations, the timing of transfers, and the balance between guided experiences and free time all matter. I work directly with our trusted partners across Italy to ensure clients feel supported while still having the freedom to explore. My role is to simplify a complex country so clients can enjoy it with confidence.

Having lived in Florence and traveled extensively throughout Italy, I bring both personal familiarity and regional insight to the trips I design. Tuscany is a region I know especially well, from navigating Florence’s historic center to planning stays in the countryside.

I also have strong ties to northern Italy, particularly the Lake Garda region, where I have family in Riva del Garda. The contrast between Italy’s alpine north and its southern regions, including Puglia and Sicily where my family roots are, gives me a broad understanding of the country’s cultural and geographic diversity.

Italy varies significantly from region to region, and understanding those differences helps me guide clients toward destinations and experiences that truly fit their interests.

I’m always drawn back to the Tuscan countryside for its quiet pace and sense of space. Also, growing up in the Oregon mountains, I also love the areas where Italy meets the mountains, especially around Lake Garda.

One of my favorite simple rituals is the evening passeggiata. It reflects something I appreciate about Italian culture: taking time at the end of the day to slow down and be present.

Italy rewards thoughtful planning. When a trip is designed well, clients experience more than major landmarks. They understand the rhythm of the place and feel comfortable navigating it.

Helping someone experience Italy in a way that feels natural, organized, and meaningful is what motivates me. My goal is always for clients to return home feeling both enriched and at ease.