THE PERFECT TUSCAN VILLA FOR YOU AND 20 OF YOUR CLOSEST FRIENDS

NOTE: THESE ARE LOUSY SCANS OF LOUSY PICTURES FROM A LONG TIME AGO, CLICK HERE TO SEE PRETTY PICTURES FROM THEIR SITE IT’S NOW ON AIRBNB — ALL THE TREES HAVE GROWN AND EVERYTHING IS EVEN BETTER. I’VE INFILLED A FEW PHOTOS FROM THEIR AIRBNB SITE.

[MONTAIONE, TUSCANY] — Let the hoards of English, Germans and Americans crowd the overly popular Under The Tuscan Sun areas south of Florence and the tourist-choked villages of Montepulciano. “Chiantishire”.

To me, I loved staying on the western edges of Tuscany centered around the cool and undiscovered town of Montaione — which Architectural Digest called “one of the prettiest towns in Italy you’ve never heard of“. The geography of this area is more farmland than grapes and a prime hunting ground. And Villa Cerretello is the perfect villa. Part of a larger private farm that includes other agriturismo villas, hunting grounds, the massive Villa Cerretello is the perfect base for entertaining lots of your friends.

Villa Cerretello

While it’s big, when you divide up the place — with individual fully outfitted mini-apartments with their own kitchens and sitting areas — it comes out waaaay cheaper than getting a hotel room in Florence. The fit and finish of each apartment is on the standards of a first class hotel. It has 10 bedrooms, with 6 double apartments and two suites.

Villa Cerretello
With its sturdy structure as a working farm building, even with 25 people you barely hear others rummage about. Everyone gets their own private space.

We had my wedding here, we had 100 friends come over for the week, spread out all over the nearby farms, so there are lots of accommodations to fit any size. At the time, in June 2000, this was part of a larger estate and this was the first building they redid. Looks like they’ve since sold them off, but you can still rent them on Airbnb and VRBO. I put links at the bottom.

Villa Cerretello pool reading
Villa Cerretello terrace party
The best part about Cerretello is the the expansive eating (partying) area by the pool, overlooking the farmland and hunting grounds on the rolling mountains below.

After day-trips exploring all the surrounding Tuscan towns, one of the best things to do is to hire a local chef (we paid $12/hour) who shop and come in and do all the cooking for you. They can even arrange a pig roast or larger catered affair. It’s incredible to come “home” each night, eat an incredible meal al fresco and share stories from everyone’s adventures. Highly recommended dispensing with bottles of wine. Just get one of the ubiquitous large vats of perfect local red and white for the week. Can’t beat it.

Fattoria Santo Stefano
If Cerretello isn’t big enough, it is part of a larger complex of agritourism villas by the same owner. Like the view of Vignola, the newer property you can see on the hill across the valley. Vignola can sleep an equal amount of people, but also can accommodate smaller groups with independent apartments in the main building — sleeping any combinations of 2-4 people. It has an equally awesome pool and outdoor dining area.

Villa Vignola

Fattoria Santo Stefano Villa Vignola

Here’s a shot from another of the villas in Fattoria Santo Stefano that we rented, called Vignola. Also a very groovy big converted farmhouse and highly recommend it as well. It was just a short walk down the road, on its own hilltop. I think it could fit up to 27 people or so, with little apartments carved out of a big old farm building, furnished perfectly.

(Photo from the Vignola VRBO page)
(Photo from their VRBO site)

What makes both of these villas great is each has its own private pool and their own covered outdoor kitchens and dining areas like over there on the right. Killer views over the surrounding rolling hills, overlooking a fenced hunting preserve with wild boar and pheasants running all over the place. Views for miles… Bring a lot of friends. Google their website for tons of better pictures and other villas on the property.

Fattoria Santo Stefano Villa Vignola pool view
It also sits on its own hilltop, so you can have amazing views for miles.
Villa Cerretello hilltop
And because it’s Tuscany, every villa gets their own hill.
Tuscany postcard carsick
You can imagine having a hundred friends in Tuscany for a week. Parties will happen. Every night. I think we went through four or five 70 litre vats of wine or something like that…do the math. I was younger then. “No sulfites!”, we said. This is my oldest and wiser brother, the life of the party, every night. I think this was around Day Five, on what I hear was a disastrous trip trying to find a Tuscan winery, which isn’t really that hard to do.

Last visited June 2000 —

More Information

Here’s a link to the Cerretello Airbnb site. And here is the link to the Vignola VRBO site. Here is the Montaione official tourism site.

Fattoria Santo Stefano map
Here’s a general map of the area, showing the villas and also others that our friends stayed in and would recommend if you’re looking for smaller places.

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