Tuscany is a wildly misunderstood region. You hear about it. You read about it. You finally decide to go. But unless you plan carefully, you may just miss it. Its large, very diverse, and it includes some of the most photogenic corners in Europe. But finding these corners requires time, patience, and a Fiat.
Fattoria Poggio Alloro (San Gimignano) – Even if you remove the San Gimignano towers from the horizon, this would have been on the list. Its a bustling working farm that welcomes visitors to shop, and stay for a meal on their terrace overlooking this..
Castello di Brolio (Chianti) – Its a castle that is a bit out of the way, but very much worth the drive. Fair entrance fee, easy to park, and splendid views of the estate from the castle. Drinks are on them! Seriously you get a free glass with your ticket
Siena to Asciano Drive– The Crete Senesi is more of a feast for the eyes than the camera due to its depth. Its like gentle rolling hills meets a desert meets Mars. As a result dont be surprised to see people stop in the middle of the road, like in a zoo. You will want to do the same.
Agriturismo Baccoleno (Crete Senesi) – You park by the gate, and walk on the path to the left until you see it. Thats the view you saw on paintings in every art gallery you’ve visited so far. Although the cypresses by the gate are photogenic on their own.
Capanna Winery (Montalcino) – Just outside Brunello Disney Montalcino is one of the Brunello founding fathers. Its worth checking it out just for the views from the back of the farm, but the farm itself is striking.
Cugusi Silvana (Montepulciano) – And you thought there wont be any mention of food in this post. Oh how silly you must feel right now. This is a Pecorino producer that sets you up with a picnic basket, and some of the best cheese and salumi in the area. All to be enjoyed in their picnic facilities just outside the store. Glorious views of Montepulciano and the country side is a major bonus. Nice alternative to the picturesque but super popular Podere Il Casale.
Genna Borborini Maria Eva (San Quirico d’Orcia) – One of the Gladiator locations. This farm is a bit overlooked when compared to the other hits on Via Cipressi (Montalcino to Pienza). You park at these coordinates, 43°03’55.8″N 11°36’43.6″E and view the villa from the gate, while humming the Gladiator theme song.
Cipressi di San Quirico d’Orcia (San Quirico d’Orcia) – Aka Cypresses Valdorcia or Circle of Cypresses. Its not just about a bunch cypresses bunched together in the middle of nowhere, but the entire most scenic middle of nowhere surrounding that middle of nowhere. Makes sense? Just go, and look around at both sides of the road.
Chapel Vitaleta (San Quirico d’Orcia) – The most photogenic little chapel in the world is a very easy drive and a short hike. But do it in the afternoon when the light is in your favor. Enjoy it while humming the Gladiator theme song because you cant get it out of your head at this point. Dont leave any luggage or anything important in the car
Le Foce (Chianciano Terme) – This is the classic zigzaging cypresses that is part of the Le Foce estate. But in order to see it, you need to take a tour of the estate. Otherwise its close to impossible to find a good view (we tried, and tried again. Gladiator humming just made it worse)