Summer is already over and after a couple trips back to Italy since the last update, we have some possibilities to share from our search.

But first some news. Dan and Roxanne, who it seems like just moved to North Carolina (they are okay), have agreed to move to Italy to manage the renovation in person. They actually agreed to move before visiting Italy, but luckily Italy delivered and they locked in their decision. They are moving abroad in a few months. No they don’t speak Italian, no they don’t have a resident permit, yes they have a 2 year old. This all makes sense.

So the pressure is on to find a place where they can live…

For the first trip, I went solo. It was great to reconnect with our Italian collaborators - wine Andrea, sports Andrea, Massimo our Architect, Giorgio our attorney, Stephano the commercialista and our ever patient Italian tutor and famous podcaster, Vera. Dan and I love our language lessons because we are experts at avoiding any actual language learning and distract Vera by discussing Italian culture instead.

We’ve found a number of interesting properties in Tuscany about an hour south of Florence close to Siena in the 2-3M euro price range. They are all “updated”, which means 20-30 years ago some minimal work was done to create a few guest rooms, and likely it was all done without permits. For an actual modern update, the properties need a lot of renovation including full interior updates with new bathrooms, new doors and windows, new HVAC systems, new plumbing, new electrical, roof repairs, insulation, foundation work, landscaping and on and on and on.

Oh, and some actual architectural permits.

Our first candidate is near Castellina in Chianti and sits on top of a hill. Building began in the 1400’s and in the 1780 the property was converted into an olive oil mill. In the 90’s it was turned into a rustic agriturismo. The property is 130 acres with olive trees, a few potential vineyards and 270 degree views of the surrounding valley.

Standing at the pool watching the sunset in totally quiet on a peaceful Tuscan hilltop, it was difficult to not just buy this property on the spot and sort out the details later. But since it was potentially Dan and Roxanne’s home for the next few years, I thought maybe I would show them a picture or two first.

There are two buildings - a farmhouse with multiple connecting apartments and a converted barn that has a few more rooms and common areas. It was updated in the 90’s so in okay condition but still needs to be fully renovated. There are about 20 bedrooms with tiny bathrooms and some reconfiguration would be needed - but a nice base layout to start with.

The land is very walkable and we could envision hiking trails through the olive groves and forest, an improved pool complex looking out across the valley and turning the renovated stable into a restaurant.

The downsides are the interior space is a little small for our project at 1,000 square meters (10,763 square feet) and the other two properties offer more than three times the square feet at approximately the same price. But more space drives up the renovation cost so this smaller property seems more manageable (and affordable).

The property has a long private gravel driveway which is nice but it’s also accessed from a rural service road that runs through the forest for a few miles off the paved highway. The first time I arrived, I thought I might be lost and any moment ambushed by friendly Chianti farmers aggressively selling wine and Finocchiona. The property is remote which is nice for privacy, but might be a little far off the main road.

Speaking of gravel roads…Italy, and Chianti in particular, love their white gravel roads called strade bianche. This is also the name of a famous bike race, Strade Bianche and Bobby and Andrea’s wine business, Strade Bianche Wines.

You can check out the listing here.

This property is perfect for wine enthusiasts as the Chianti “recipe” was created next door at Castello di Brolio by Italy’s second prime minister and winemaker, Bettino Ricasolie.

This property is enormous and overwhelming at first. It’s over 160 acres, has 9 buildings including a villa, restaurant, yoga center, wine cellar and even a dedicated jam-making room. It has a beautiful view looking out at the Castello di Brolio, but really the biggest selling point is the jam-making room.

When I read that this property had a thermal springs I immediately pictured a swimming pool with steam rising in the winter and soaking hot tubs amongst the vineyards, a steam power plant providing electricity and unlimited hot water for free heating! We were ready to purchase without even visiting.

But then we learned that thermal springs aren’t that hot, more like 80 to 85 degrees. And they emit toxic gas including carbon dioxide and hydrogen sulfide that requires special equipment to remove so you don’t kill your guests. It also doesn’t smell great.

This property is a little further south, near Asciano in the Sienese, made famous by being the home of Maximus the gladiator in the movie Gladiator. In the second scene of what is surely a documentary, filmed in the Valle d’Orcia, Maximus stands alone in one of these wheat fields, feeling the wind-blown grains brush against his hands, and this symbolizes the afterlife. If we bought this place, we could become famous filmmakers, write scripts in the sun and host our celebrity friends. Dan and I are filmmakers and did develop an Oscar worthy script while driving across country, so if this hospitality gig doesn’t work out, we’ll likely move to Hollywood and dust off “White Sands”.

This is a large property with an agriturismo building with guest apartments, an old hotel that has been closed for a century and a villa that overlooks the pool. A standout killer feature is there are underground tunnels that connect the buildings with the pool.

We need to think more about the thermal springs and how that fits with our concept, the maintenance efforts and what this project would cost to renovate. You can see more photos at the listing.

So those are a few of the possibilities we’re considering. Do we pick the place where Chianti was born, the place with views that feel heavenly, or the place with underground tunnels that seem like a great place for hospitality hijinks? Unfortunately, we will need another trip to Italy to find out.