A 5-Day Italian Real Estate Retreat

Invest, understand, and access the Italian property market from the inside.

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*Limited to 14 participants

What You’ll Experience

An intimate real estate retreat in Tuscany for international investors and entrepreneurs.

Designed to provide clarity on how the Italian property market really works, direct access to opportunities, and informed decision-making.

Four men standing on a grassy lawn, talking and drinking wine, with hills and trees in the background and a bush with flowers on the right side.

  • Private Tuscan estate, exclusively for the group

  • Curated group of up to 14 investors and operators

  • Private property viewings, including residential and hospitality assets

  • Educational sessions on Italian real estate, tax structures, and legal frameworks for foreign buyers

  • Time intentionally built in for discussion, analysis, and networking

  • Cultural and gastronomic experiences in the Tuscan countryside

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The 5-day Itinerary

A clear structure that balances private viewings, investment education, and the Tuscan lifestyle.

A group of people gathered outdoors at a social event, listening to a man speaking, with drinks in hand, under a shaded area during sunset.

Day 1: Arrival & Welcome

  • Guest arrivals and check-in

  • Welcome aperitivo

  • Opening dinner and introductions

Man with dark hair tied in a bun opening a bottle of red wine while a man with curly light hair watches. They are sitting at a table with several glasses of red wine and water, set with plates and utensils, in a rustic restaurant with wood beams and warm lighting.

Day 2: Market & Deal Flow

  • Morning session: Italian market overview

  • Property viewings

  • Wine tour + lunch at a local agriturismo

  • Afternoon debrief: numbers, renovation assumptions, red flags

  • Evening group dinner

Aerial view of a large estate with multiple buildings, a swimming pool, outdoor seating, and surrounding trees and greenery.

Day 3: Legal, Tax & Due Diligence

  • Morning session: buying process, due diligence checklist, common traps

  • Guest expert Q&A: tax basics, structuring, residency and compliance angles

  • Property viewings

  • Afternoon cultural experience (local town visit)

  • Evening dinner and informal deal discussion

A scenic view of a countryside property with a white two-story building with a red tiled roof, a swimming pool, and surrounding greenery, fields, and mountains in the distance.

Day 4: Hospitality Business Models

  • Morning session: turning real estate into yield (STR & boutique hospitality)

  • Property viewings

  • Afternoon cooking class

  • Closing reflections and takeaways

  • Farewell dinner

A scenic view of rolling hills in Tuscany, Italy, with a winding dirt road lined with tall cypress trees, and a farmhouse in the distance under a vibrant sunset sky.

Day 5: Departure

  • Breakfast and departures

Guest Speakers & Contributors

Throughout the retreat, you’ll have direct access to professionals actively operating in the Italian real estate and hospitality space.

Tom

Property advisor for international buyers in Italy, Spain, Portugal and France.

A man with dark brown hair, a trimmed beard, smiling, wearing a white shirt and dark blazer, in a room with a framed photo on the wall.

Paulo

Co-Founder of Si Retreats and operator within the Italian hospitality industry.

A young woman with long, wavy brown hair, wearing a black blazer and white blouse, smiling with arms crossed, standing against a plain light background.

Francesca

Lawyer and Italian tax expert with over 15 years of experience.

A man with dark hair, glasses, and a serious expression, dressed in a dark blazer and white shirt, standing in a bright indoor setting.

Marco

Real estate agent with over 10 years of experience in the italian market.

Pricing

This retreat is designed as a fully immersive, all-inclusive experience, allowing participants to focus entirely on learning, analysis, and connection.

Sunset over a rural countryside with a large brick estate with an outdoor pool, surrounded by fields, trees, and vineyards.

  • Participants will stay in private apartments within the estate, each with its own bathroom and independent access. Guests also have access to the estate’s private swimming pool, gym, and outdoor areas throughout the retreat.

    • 5 days, 4 nights accommodation at a private Tuscan estate

    • Daily breakfast and all meals

    • All educational sessions, workshops, and guided discussions

    • Private property viewings and on-the-ground market access

    • Sessions with real estate, tax, legal, and hospitality professionals

    • Group transportation during scheduled activities and viewings

    • Cultural and gastronomic experiences during the retreat

  • €3,500 - Double Occupancy
    €4,000 - Single Occupancy

    All prices are per person and include the full retreat experience as outlined above.

Limited to 14 participants to maintain depth of conversation and a high-quality group experience.

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FAQ

  • The retreat is hosted at Agriturismo S. Angelo, a private estate located in Brolio, in the Val di Chiana area of Tuscany. The estate is set in the countryside and exclusively reserved for the group during the retreat.

  • The nearest airports are Florence (FLR) and Perugia (PEG),. Detailed arrival instructions and recommended transfer options will be shared after confirmation. Group transportation is provided during scheduled retreat activities.

  • Yes. Single occupancy includes a private apartment with a private bathroom. Double occupancy is intended for participants attending together who choose to share an apartment.

  • Guests have access to the estate’s private swimming pool, gym, outdoor areas, and common spaces throughout the retreat.

  • The price includes accommodation, daily breakfast, group meals, all educational sessions, property viewings, group transportation during scheduled activities, cultural experiences, and full on-site coordination by SI Retreats.

  • Flights to and from Italy, travel insurance, and any personal expenses outside the official program are not included.

  • Property viewings may include residential homes, villas, countryside estates, and hospitality assets such as agriturismi or boutique hotels.

  • The retreat is designed for participants who are seriously considering investing or operating in Italy. While no prior ownership is required, discussions assume a genuine interest in real estate investment rather than casual exploration.

  • Sessions will cover general frameworks, structures, and considerations related to Italian real estate, taxation, and legal processes. The retreat does not provide personalized legal or tax advice. Participants should consult their own advisors before making decisions.

  • Participation is limited to 14 participants to ensure depth of discussion, access to speakers, and a high-quality group dynamic.

  • The retreat is conducted in English.

  • Yes. Participants may attend together and choose double occupancy if they wish to share accommodation.

    • Full refund within 30 days of purchase

    • 50% refund if cancellation is made up to 30 days before the retreat start date

    • No refunds for cancellations made within 7 days of the retreat start date

    All refunds are processed to the original payment method.

An aerial view of a large estate with a main brick house, a separate gazebo structure, and extensive landscaped gardens, surrounded by rolling fields and farmland in the countryside.