Insiders

Getting to Know Italy (Starting in Umbria)

Before you commit to a major move, you need more than pretty photos and influencer reels. You need to feel actual streets under your feet, talk to real people, and sense: “Could I live here?”

That’s what these experiences are for.

We design high-quality, custom days in Umbria that balance sightseeing with real-life texture—markets, conversations, small discoveries. Experiences are private or very small-group, designed around you.

Project OverviewSee the full report.

Day 1 – Perugia & Lake Trasimeno

Morning: Stroll Perugia’s historic center with a local—piazzas, neighborhoods, everyday spots you’d actually use if you lived here. Coffee, people-watching, and a simple explanation of how life works in a hill town.
Lunch: Family-run trattoria with local dishes and a chat about food culture, shopping, and seasonal rhythms.
Afternoon: Drive out to Lake Trasimeno—visit a lakeside village, walk along the water, and talk through what lakeside living is actually like in terms of seasons, crowds, and cost of living.

Day 2 – Hill Towns & Everyday Life

Choose a combination like Gubbio, Assisi, Todi, or Orvieto depending on what you’re curious about.

Walk the town with Matteo or Loredana: housing types, neighborhoods, “this is where people actually buy groceries,” local festivals.
Stop for wine, chocolate, or olive oil along the way, depending on your interests.
End with a casual debrief over aperitivo: How did each town feel? Could you imagine yourself here?

If food and wine are a big part of your dream, we build days around your taste:

Chocolate – Visit the Perugina/Bacio story, plus smaller artisanal producers if you like.
Wine – Explore Sagrantino and other local wines, meet winemakers, and do tastings that include real conversations about seasons, production, and community—not just “sip and go.”
Extra Virgin Olive Oil – Visit mills, taste different oils, learn how locals actually use them, and (in season) see or participate in harvest.
Truffles – Join a truffle hunt, a cooking lesson, and a tasting that ties it all together.
Norcinery (cured meats) – Learn about Umbrian salumi, salami, and sausages—the everyday food culture behind the menus.

You can combine a couple of these themes into one day, or spread them out over several.

For many people, the draw of Umbria isn’t just food—it’s something deeper.

We create days that follow your soul:

Spiritual Umbria – Visit key sites tied to saints, rebels, and the people (and stories) that shaped this region’s spiritual identity.
History through the ages – Trace a line from Etruscans and Romans through the Middle Ages to today, using towns, monuments, and small details as your “textbook.”
Art lovers’ day – From church wall paintings and frescoes to contemporary art spaces.
Nature & quiet – Lakes, rivers, waterfalls, and hill walks timed for sunrise or sunset.
Small unknown villages – Charming, unspoiled places where life is still very local and tourism is a side note, not the main story.

When timing lines up, we can also design around:

International events like Umbria Jazz (Perugia) or Festival dei Due Mondi (Spoleto).
Traditional festivals & Palios like the Ceri in Gubbio or the Quintana in Foligno.

How these experiences work

In plain terms:

You tell us your timeline, interests, and energy level.
We suggest 1–3+ days of experiences tailored to where you’re at—whether you’re very early in the process or much closer to a decision.
Matteo and Loredana handle local logistics and guiding; Craig and Cindi help connect what you’re seeing back to your larger decision about Italy.

Experiences are designed as high-quality, private or very small-group days with a mix of:

Town/countryside time
Real conversations with locals
Space to simply look, feel, and imagine

Learn More

One,
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Talk with us about a custom day in Umbria

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