OCTOBER 13-17, 2026 · TUSCANY, ITALY · LIMITED TO 16 GUESTS
Stop Dreaming
About Italy.
Come Find Out If You
Belong Here.
A 5-day immersive retreat in the heart of Tuscany - exploring properties, understanding the buying process, and deciding whether owning a piece of Italy is actually within reach for you.
October 13-17, 2026 · Val di Chiana, Tuscany · Limited to 16 guests
Property Viewings €70k-€1M+
·
Expat Panel Discussion
·
Wine Tasting with Producers
·
Cooking Class at the Villa
·
Personal Roadmap Session
·
Visa & Residency Guidance
·
Property Viewings €70k-€1M+ · Expat Panel Discussion · Wine Tasting with Producers · Cooking Class at the Villa · Personal Roadmap Session · Visa & Residency Guidance ·
IS BUYING PROPERTY IN ITALY ACTUALLY POSSIBLE?
You've been thinking about this for a long time.
You've read the articles. You've bookmarked the properties. You've had the conversation over dinner a hundred times: "Wouldn't it be incredible to have a place in Italy?"
But there's always a reason to wait. You don't know where to start. The buying process feels complicated for foreigners. You don't know if the numbers really work, or whether you'd actually use it enough to justify it.
Here's what we know after working with hundreds of international buyers across Spain, Italy, Portugal, and France: the process is more straightforward than you think - once you understand how it works.
That's why we built this retreat.
"Could I actually live here?"
27,000+
AFFORDIHOME SUBSCRIBERS ASKING THE SAME QUESTION WEEKLY
This retreat was built to answer that question in an honest and practical way.
WHAT THIS IS
An Exploration,
Not a Sales Pitch.
The Italian Real Estate Retreat combines authentic Tuscan experiences with practical, jargon-free education and curated property viewings - across price ranges from €70k to €1M+.
You leave with real clarity about whether buying property in Italy makes sense for you, and a personal roadmap for what to do next. Whether that means moving forward in three months or three years.
Three things happen over five days:
Live It First
Experience authentic Italian daily life - not the tourist version. Slow mornings, long lunches, village aperitivos, and real conversations with locals and expats who made the move.
Understand the Path
Expert sessions on Italian visas, residency options, taxes, and the property buying process - including how Italy's flat tax regime works for foreign residents, and what the elective residence visa actually requires. Practical, accessible, zero jargon. You leave with a written personal roadmap.
See Real Properties
4-5 curated property viewings across price ranges, from affordable renovation projects to turn-key Tuscan estates. Private. No pressure. Just honest looks at what's actually available in today's market - and what things really cost.
WHERE YOU’LL STAY
Agritusimo
Sant’Angelo
VAL DI CHIANA · TUSCANY
Set in the rolling hills of Val di Chiana - between the great art towns of Tuscany and Umbria - Sant'Angelo is a working estate surrounded by olive groves, vineyards, and open countryside.
This is the Italy you've been imagining. And it's where we'll spend four nights together.
The estate offers private rooms across 10 elegant apartments, a large outdoor pool, gym, and generous shared spaces - ideal for the unhurried conversations this retreat is built around.
THE EXPERIENCE
Five Days That Could Change Your Direction.
We've designed every hour to feel unhurried and natural - like you've been living in Tuscany for years, not ticking boxes on a tour.
You arrive at Sant'Angelo and settle into your private room overlooking the Tuscan valley. The evening starts with a welcome aperitivo - good wine, no agenda, just the beginning of what will feel like a very natural conversation with people who share your exact curiosity.
After morning yoga and breakfast, we head into Val di Chiana for a wine lunch with local producers. The afternoon is yours - dolce far niente. In the evening, a candid expat and expert panel: honest stories, real numbers, and the things they wish they'd known before buying property in Italy.
Morning opens with "Your Path to Italian Property" - a practical session on the buying process, residency pathways, and how ownership works as a foreigner. Then we head out for four curated property viewings across price ranges, with a long lunch at a local osteria in between. Individual consultations in the evening.
A lawyer session in the morning demystifies the legal and tax side - what you actually need to know as a foreign buyer, including how Italy's property taxes work and what the flat tax regime means for new residents. Then the afternoon belongs to the kitchen: a hands-on cooking class at the villa with a professional chef. The evening ends with drinks, an open bar, and the kind of conversations that only happen on the last full night.
A final breakfast, then your Personal Roadmap session: where do you go from here? You leave with a written action plan, a curated list of vetted expert contacts (lawyers, surveyors, mortgage advisors), and access to the alumni community. Farewell lunch at the villa before departure.
INVESTMENT
All-Inclusive.
No Surprises.
Everything from the moment you arrive to the moment you leave - accommodation, all meals, expert sessions, and property viewings.
- 4 nights in a private room at the villa
- All meals, breakfast to dinner, with wine
- All experiences & expert sessions
- 4–5 curated property viewings
- Personal roadmap session
- Alumni community access
Reserve your spot with €900 today. Balance of €2,099 due 60 days before arrival.
- Shared private room for 2 at the villa
- All meals, breakfast to dinner, with wine
- All experiences & expert sessions
- 4–5 curated property viewings
- Personal roadmap session
- Alumni community access
Reserve both spots with €1,470 today. Balance of €3,428 due 60 days before arrival.
THIS RETREAT IS FOR YOU IF…
You'll love this if…
- You've seriously considered buying property in Italy but don't know where to start
- You want to understand the process - visas, taxes, buying steps - without wading through conflicting information online
- You're financially ready to explore, even if you're not ready to commit yet
- You want honest answers about what the Italian property market actually looks like in 2026
- You'd love to meet other people who are in exactly the same place
This isn't for you if…
- You're looking for a passive villa vacation with no depth
- You want a high-pressure investment seminar environment
- You're not open to the possibility of actually making a move
QUESTIONS
We've Heard Them All.
If your question isn't here, get in touch - we're happy to chat through anything before you decide.
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Not at all. Most guests come with genuine curiosity but no firm commitment. The whole point of the retreat is to help you work out whether buying in Italy makes sense for you - and what it would actually look like. Plenty of people leave ready to move forward. Others leave with a clearer sense of what they need to figure out first. Both are valuable outcomes.
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We curate 4–5 viewings across a broad range - from renovation projects under €150k to fully restored Tuscan estates closer to €1M. The goal is to give you a realistic picture of what's available in today's Tuscan market, not a cherry-picked highlight reel. Property types will include farmhouses, village homes, and countryside estates.
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No. AffordiHome operates exclusively on the buy side - we represent international buyers, not sellers. We don't earn commissions from the properties you view. Our interest is in giving you an honest, well-informed picture of what buying property in Italy actually involves.
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A qualified Italian property lawyer walks you through what foreign buyers actually need to know: the purchase process, the role of the notaio, what due diligence involves, property taxes, and - for those interested - an overview of Italy's residency pathways and the flat tax regime for new residents. Accessible, no jargon.
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Not at all. The group is deliberately small (16 guests maximum), and the format is designed around conversation and connection. Many guests come solo. You will leave knowing people who share your exact situation.
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Early Bird bookings come with a free cancellation until April 30. After that, the following applies to all bookings:
Before June 1: Full payment guests receive a 75% refund; deposit guests receive 50% of their deposit back.
Between June 1 and July 1: Full payment guests receive a 50% refund; deposit guests receive 25% of their deposit back.
After July 1: All bookings are non-refundable. Remaining balances for deposit guests are due by August 1.
At any point, you can transfer your spot to someone else at no extra cost - just let us know at least 14 days before the Retreat.
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Everything: accommodation for 4 nights, all meals from arrival dinner to farewell lunch, wine included, all experience activities (wine tasting, cooking class), all expert sessions, property viewings, individual consultation time, personal roadmap session, and access to the alumni community. Flights and transfers to and from the property are not included (options will be provided).
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Yes. The programme is designed so that even guests who aren't focused on the property side will have a genuinely enjoyable and enriching experience - the food, the region, and the company are the draw for everyone.
FROM OUR COMMUNITY
People Who've Been
Where You Are.
Working with Anastasia and Tim was such a gift. From day one, their professionalism and thoughtful communication put us at ease. They listened closely to our feedback, tailored her property reports to fit our style, and when the time came, went the extra mile to arrange multiple showings in Italy. We can’t recommend them enough.
We had a wonderful stay at Agriturismo S. Angelo. The property is beautifully located in the Tuscan countryside, offering a quiet and relaxing atmosphere. The rooms are clean, comfortable, and well maintained, with a charming rustic style that fits perfectly with the surroundings.
Beautiful location! Everything was perfect! Good air conditioning, fantastic pool, and we had a wonderful event! Keep up the good work! The food was also fantastic! We'll definitely be back!
THE ORGANIZERS
Meet the People Behind the Scenes.
Between us, we bring 15 years of Italian hospitality operations, a real estate community of 27,000+ people, and a shared belief: the only way to know if Italy is for you is to come and see for yourself. That's why we built this retreat.
A decade living and investing in Mediterranean Europe, working exclusively for buyers.
Serial entrepreneur turned property advisor, working directly with buyers across the mediterranean
Co-founder of SI Retreats and hospitality operator in Italy with hands-on experience across properties in the Italian countryside.
Only 16 Spots.
October Goes Fast.
OCTOBER 13–17, 2026 · TUSCANY
16 guests. 5 days. One question worth answering - Is buying property in Italy actually for you? This retreat was built to answer that question - honestly, practically, and in the best possible setting.
Early bird pricing ends May 1, 2026 · Secure checkout via Stripe