Agriturismo in Tuscany

It does not hit everything on your wish list, but I stayed at Agriturismo Marciano just outside of Siena (but certainly with a countryside feeling). It's the #1 "Specialty Lodging" in Siena on Trip Advisor.

The agriturismo produces organic wines and olive oils. It is surrounded by vineyards. It is a rustic but comfortable farmhouse with an appearance and furnishings that line up with what most people think of when they think of Tuscany (rooms can be viewed on their website). It has a nice courtyard/garden for relaxing and enjoying a glass of wine at the end of the day. Rooms do not have balconies, but have a nice view out the window. I found the hosts warm and inviting. They offer a cooking class. They offer a class on vine growing and wine making (with a tasting). They provide a short early evening tour of the farm and explain what it makes. There is a large open kitchen with a large table where guests enjoy breakfast AND where the hosts serve wonderful, wonderful 4-course dinners (with each course paired with one of the agriturismo's wines). The dinners there were easily the best food we had in Italy (dinners are offered based on interest level of the guests). There were around 10-12 people at the 2 dinners we had there. We enjoyed our interaction with other guests around the dinner table and in the common areas. Other guests over our 4 nights there included a newlywed couple from the US, an adult mother/daughter pair from the US, a middle-age couple from the US that we later encountered in Florence, a retired couple from Michigan, a young couple from Poland (interesting to get their take on Russia and its politics), a small family from Germany, and a middle-age couple from Italy. Location is right outside Siena. The agriturismo offers bikes for guest use (I don't think there is a rental charge). There are several friendly cats that hang out around the property and in the common areas. Unfortunately, there is no pool.

Virtually every farm in Tuscany has apartments and rooms for rent for secondary income. They just average 20 acres.
I like the area outside of Certaldo and San Gimignano which is west of Poggibonsi. There are many other fine hilltowns in the region with agriturismoa in the countryside.
Go to Google Maps online. Pick a town, or area outside the town. Expand (zoom) the map and little icons of a bed wil! show.. Click on the bed icons and up pops the info on the agritiurismo. It often gives their direct email address.

Many such properties can also be found on Booking.com.

Not sure if this ticks all the boxes....but our family of 4 stayed in Apt. Ginestra at agriturismo IL Rosolaccio which is just outside of San Gimignano. www.rosolaccio.com We had a lovely 2 bedroom/1 bathroom apt. located on the first floor (2nd floor in the U.S.) with beautiful views of the Tuscan countryside. No Balconies here but there is a lovely pool and I do remember seeing some
cats:) You can check out their website for breakfast, dinner and cooking class info. We did not have any meals here so can't speak to that. It is also very close to the village of Certaldo where you can take a funicular to the Medieval upper area called Certaldo Alto. Besides Certaldo, we visited San G. several times esp. in the evenings when the many daytrippers are gone, Volterra, Siena, Monteriggioni and several villages of Chianti region--Castellina, Radda & Gaiole in Chianti, etc. One day we drove to Pisa as our boys really wanted to climb the tower. Have also stayed at several other agriturismi in Tuscany but they would not check as many boxes. We were here in summer and there is no A/C and it was HOT!! One of our memories we laugh about is me pointing to a fan in a small gift shop in Monteriggioni. The elderly lady did not speak English but she knew what I was asking. She said Mercatone Uno and we stopped there on the way back to our apt. and bought a fan. Even the evenings did not cool off much and that fan was a lifesaver!! We left it there as our final destination was Rome and our accommodatioin had A/C. Wasn't the last time we have purchased a fan on travels in Europe:) Buon Viaggio!!

Thanks all for the information. I was dubious that I could get most on my wish list but you have definitely given me at least 90%. Started to get excited even if it isn't until May 2019.

Thanks again,
Patti

Patti,
Look at Sant’ Antonio country resort near Montepulciano. We have stayed there twice and will be there in October. Great location, near other small towns that are easy to visit/see. They offer wonderful accommodations and are very helpful with anything you might need or have questions about.
Dana

santantonio.it is their website.

Look into IL Greppo, in the Province of Montepulciano. It is a working winery with many amenities. It is just minutes from the town of Montelulciano.

http://www.ilgreppo.com/index.php

That looks amazing, Charlie.

We stayed there in 2003, before they did a lot of enhancements to it. And it was wonderful then.

And here is another one ...
http://www.agriturismo-casanova.it/

Seems to cover what you want. We stayed in their apartment for 7 nights. We had dinners there maybe half the time ... theirs is a chiana (sp?) cattle farm so you’ll want to like beef!

Nice central location for southern Tuscany.

So many choices. So little time!

Thanks Daniel,
Casanova looks amazing.