HOW TO MOVE TO ITALY: Lessons from ViaMonde Founder Jennifer Sontag

In this episode of The Armchair Expat Podcast, Shannon sits down with Jennifer Sontag — serial entrepreneur, expat, and founder of ViaMonde, a bespoke agency that simplifies relocations to Spain and Italy. Jennifer’s story is one of bold reinvention, deep resilience, and the transformative power of starting over in a new country.

Jennifer shares her journey from growing up in St. Louis to living in China, and eventually rebuilding her life on the island of Sicily. After a major personal and professional crossroads, she spent five years redefining everything — her career, her purpose, and ultimately her sense of home. That path led her to found ViaMonde, where she now guides others through the complex, emotional, and deeply personal process of moving abroad.

Together, Shannon and Jennifer dive into:

• How Jennifer rebuilt her life from scratch and found clarity on a hillside in Sicily
• Her experience living in China and how it shaped her worldview
• The surprising challenges of obtaining Italian citizenship
• The cultural contrasts between Italy and Spain — and why one may suit you better than the other
• The unique pressures women face during midlife transitions
• Why asking for help during a relocation isn’t a weakness — it’s essential
• The emotional, logistical, and identity-level layers of moving abroad
• How ViaMonde was created from Jennifer’s own hard-won lessons
• Encouragement for anyone dreaming of a slower, more intentional life abroad

Jennifer reminds listeners that reinvention is possible at any stage of life — and that building a new chapter overseas isn’t just a fantasy reserved for the brave few. It's a tangible, navigable path with the right support.

Connect with Jennifer

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