About Authentic Umbria

So...what is Authentic Umbria actually about?

If you’re a U.S. citizen approaching retirement (or already there), you might be feeling a mix of:

  • “We could really do this, right?”
  • “Are we crazy?”
  • “Where on earth do we even start?”

Authentic Umbria exists to sit in that space with you—between daydream and decision—and give you honest, grounded support.

Who this is for

We’re a good fit if you are:

  • A U.S. citizen or couple with some financial flexibility—looking for smart decisions, not the cheapest path.
  • Thinking about part-time or full-time life in Italy in the next 6–24 months.
  • Wanting to avoid painful surprises around culture, logistics, and “we didn’t know what we didn’t know.”

You don’t need everything figured out. You just need to be genuinely curious and open.

What makes us different

Most relocation help falls into one of two buckets:

  • Big agencies that handle logistics but feel impersonal and transactional.
  • Influencers who show the lifestyle, but not the real decision-making or trade-offs.

We’re neither.

We’re a boutique advisory made up of:

  • Craig & Cindi – Americans who’ve actually walked the road you’re considering: visas, choices, doubts, logistics, and the emotional side of leaving and arriving.
  • Matteo & Loredana – Umbrians with local expertise, bilingual skills, and deep roots in the region. They know the culture, the systems, and the places that actually work for real life.

Our whole model is built on staying small and high-touch—about 5–10 clients a year, not hundreds.

What we actually help you with

You can think of our work in four buckets:

1. Big-picture clarity

We help you answer questions like:

    • Part-time or full-time?
    • City, university town, lake, or quiet hilltop village?
    • What’s a realistic budget and lifestyle for us?

You leave with a clearer sense of whether this is a “yes,” a “not yet,” or a “beautiful dream we’ll enjoy as travelers instead.”

2. Cultural orientation & lifestyle planning

We talk through:

    • How daily life actually works here (shopping, driving, healthcare, seasons, social life).
    • What might surprise you coming from the U.S.
    • How to set expectations so Italy feels like a great fit, not a constant frustration.

3. On-the-ground experiences in Umbria

If it makes sense, we move from Zoom to real life.

Together with Matteo and Loredana, we design custom days in Umbria where you:

    • Visit towns like Perugia, Assisi, Gubbio, Todi, Orvieto, Spello, Foligno, Spoleto, and Lake Trasimeno.
    • Follow your taste—wine, chocolate, olive oil, truffles, cured meats, markets, family-run trattorias.
    • Follow your soul—spiritual sites, art, history, nature, festivals, and lesser-known villages.

You’re not “doing a tour.” You’re trying on a possible life.

4. Connections and a realistic roadmap

We don’t pretend to be everything. Instead, we:

    • Introduce you to vetted professionals—real estate agents, notaries, attorneys, tax specialists, and more.
    • Help you understand who does what and in what order.
    • Keep our role clear: we advise, translate (literally and figuratively), and walk alongside you—you make the final calls.

What we don’t do (on purpose)

To keep everyone sane and clear, we don’t:

  • File your visa or residency paperwork.
  • Act as your real estate agent or long-term property manager.
  • Manage construction or renovation projects.

We’ll help you understand these pieces and connect you with the right people—but we stay in our lane so you always know who’s doing what.

How working together usually flows

You don’t have to follow this exactly, but most clients move through:

  1. Curiosity Call – A relaxed video call to hear your story, answer initial questions, and see whether we’re a fit for each other.
  2. Clarity & Options – A deeper session where we map your goals, timeline, budget, and constraints into realistic options and next steps.
  3. On-the-Ground Time in Umbria – Custom experiences (1–3+ days) to help you get a felt sense of whether this region—and certain towns—are “yours.”
  4. Decision & Roadmap – If Italy still feels like a yes, we help you outline a phased plan for the next 6–24 months and connect you with the right people.

Schedule a Curiosity Call


We'd love to answer your questions!


Let's Connect
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Talk with us about a custom day in Umbria


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