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.

Not ready to commit—just ready to explore?

We’ll help you sort the dream from the doable.
Start the Conversation

Is this you?Who This Is For

We’re a great fit if you want smart decisions, real context, and fewer surprises.

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Beyond the Dream

You’re exploring part-time or full-time life in Italy as a real next phase—not just a fantasy.

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Thoughtful Timeline

You’re thinking in the next 6–24 months, not trying to move overnight.

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A Smart Approach

You have financial flexibility and want the smartest approach, not the cheapest.

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Honest Guidance

You’re excited, but you also want clarity about tradeoffs, logistics, and what daily life really feels like.

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

What Makes Us Different

Most help falls into two buckets. We’re neither...

Big agencies (not us!)

  • Strong on logistics
  • Can feel impersonal
  • Often transactional

Influencers (not us!)

  • Inspiring lifestyle glimpses
  • Less of the real tradeoffs
  • Hard to turn into a plan

Authentic Umbria

  • Boutique, high-touch advisory
  • Two Americans + two Umbrians
  • Grounded, honest, local, human
  • Designed to stay small

We intentionally work with about 5–10 clients a year so this stays personal and carefully guided.

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.  [Meet Craig & Cindi]
  • 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.  [Meet Matteo & Loredana]

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

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.

Tailor-Made for YouHow We Help

Explore More

From Curiosity to ConfidenceYour Italy Decision, Made Clearer

We guide you through four grounded, high-touch focus areas.

  • 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?

    Outcome: 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.”

  • 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.

    Outcome: Italy feels exciting and doable—not confusing and frustrating.

  • On-the-ground experiences in Umbria

    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.

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

  • Connections + 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.

    Outcome: You move forward with confidence and the right people around you.

Schedule a Curiosity Call

A relaxed Zoom conversation to answer your questions.

Let's Connect
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Four-Step PathwayHow Working Together Usally Flows

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Curiosity Call

A relaxed conversation to hear your story and answer early questions.
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Clarity & Options

We map your goals, timeline, budget, and ideal lifestyle into real choices.
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On-the-Ground Time in Umbria

Custom experiences (1–3+ days) to see what feels right.
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Decision & Roadmap

If Italy still feels like a yes, we outline next steps and connect you with trusted experts.

Talk with us about a custom day in Umbria

Let's Connect

Who This Is For

We’re a great fit if you want smart decisions, real context, and fewer surprises.

A realistic life chapter

You’re exploring part-time or full-time life in Italy as a real next phase—not just a fantasy.

A sensible timeline

You’re thinking in the next 6–24 months, not trying to move overnight.

Thoughtful investment

You have financial flexibility and want the smartest approach, not the cheapest.

You want the honest version

You’re excited, but you also want clarity about tradeoffs, logistics, and what daily life really feels like.

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

Tailor-Made for YouHow We Help

How We Help

Tailot-Made for YouHow We Help

  • 1. Big-picture clarity

    We help you answer the essential questions: Part-time or full-time? What kind of town fits you? What’s a realistic lifestyle and budget? Outcome: You leave with a clearer sense of whether this is a yes, a not yet, or a beautiful dream you’ll enjoy differently.

  • 2. Cultural orientation & lifestyle planning

    We talk through what real life looks like here— daily rhythms, expectations, and the differences that matter most for Americans. Outcome: Italy feels exciting and doable—not confusing and frustrating.

  • 3. On-the-ground experiences in Umbria

    We design custom days where you: Explore towns and villages at a livable pace Follow your taste (food, wine, olive oil, markets) Follow your soul (history, art, nature, festivals) Outcome: You’re not “doing a tour.” You’re trying on a possible life.

  • 4. Connections + a realistic roadmap

    We don’t pretend to be everything. We: Introduce you to vetted professionals Help you understand who does what—and when Keep the plan phased and clear Outcome: You move forward with confidence and the right people around you.