Jessica
Senior Travel Advisor
Jess grew up in the mountains of Central Oregon, but Italy was always part of her story. Her great-grandparents emigrated from Puglia and Sicily, and family conversations often included stories of her father’s time living in Florence. Those early influences shaped a lasting connection to the country.
At nineteen, she moved to Florence to work as a nanny. It was her first time in Italy, and it confirmed what she had long suspected: this was a place she wanted to understand beyond a short visit. In her late twenties, she obtained dual Italian citizenship and returned to live in Florence for a year and a half. Living there gave her a practical understanding of daily Italian life that continues to inform the way she designs travel experiences today.
As a Travel Advisor with Italy With Bella, she designs custom itineraries that are thoughtful, well-paced, and tailored to each client’s goals. She oversees every detail, from boutique hotel selection and private transfers to curated experiences and restaurant reservations, ensuring each element works together seamlessly.
She is especially attentive to logistics and flow. The spacing between destinations, the timing of transfers, and the balance between guided experiences and independent time all play a role in the overall success of a trip. By working closely with Italy With Bella’s trusted partners throughout Italy, she ensures clients feel supported while maintaining the freedom to explore comfortably.
Having lived in Florence and traveled extensively throughout Italy, she brings both personal familiarity and regional insight to the itineraries she creates. Tuscany is a region she knows particularly well, from navigating Florence’s historic center to planning stays in the countryside.
She also has strong ties to northern Italy, especially the Lake Garda region, where she has family in Riva del Garda. With family roots in Puglia and Sicily, she appreciates the distinct cultural differences between northern and southern Italy. This broad understanding allows her to guide clients toward destinations and experiences that align naturally with their interests and travel style.
She is consistently drawn to the Tuscan countryside for its quiet pace and open landscapes. The areas where Italy meets the mountains, particularly around Lake Garda, remain personal favorites.
One ritual she always appreciates is the evening passeggiata, a simple tradition that reflects Italy’s emphasis on slowing down and enjoying the everyday.
She believes Italy rewards thoughtful planning. When designed well, a trip offers more than a checklist of landmarks; it provides a sense of ease and connection to place.
Her goal is for clients to return home feeling confident, enriched, and deeply satisfied with how they experienced Italy.
