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.

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.

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.

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.

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.

— 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.