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)

There’s a common belief in the travel community that vacations should be all about you, and what you like to do. Stay in the type of accommodations you like. Do the things that interest you. Eat the things you enjoy the most in the setting you feel most comfortable in. “What type of food do you like?” is a common response to someone seeking dining advice on the travel boards. It rarely makes sense to me. But knowing exactly what you want and getting it when you want it, doesnt sound so wrong. Some may argue its living life to the fullest. In fact I’m often jealous of people who travel with their favorite cigars, coffee, rum, prunes. Yes, prunes. Prunes give people comfort.
You start this adventure before you even enter the place. About 15-30 minutes before in fact. To ensure a table its recommended to come before they open, otherwise you get an approx time slot, or risk missing out. If its lunch time, and they run out of space and time, they can put you on a list for dinner. Once they open (may not be on time), everyone surrounds the list reader like he is about to read the chosen names in a high school play, and about to give them free Focaccia. Then he goes “Prego” and bam, a mad rush inside. You are shown to your table or table that you’ll share with others.
July 20, 2019 Update:
I tell ya. There are some beautiful places on this planet. Some of which look like belong to another planet. I can think of some parts in south Utah like Lake Powell, and Horseshoe Bend in Arizona that look like something you may see in science fiction movies. The common theme is usually color. And if you come at the right time to this part of Umbria you might just see every color imaginable. If you come at the wrong time as we did, its spectacular, still.



Wind Sand Chicken at Pinch Chinese (Soho)– A tasty rendition of a Hong Kong classic. The whole bird is cooked like Peking duck. Two days of Marinating (cinnamon, star anise, other herbs and spices), drying, spanking, repeating. The skin gets thin and crispy, and the flesh redefines moist. Garnished with the sand like fried garlic which gives it the name. Update: Just made resvs for 4 this Saturday night to have this again
Pollo alla Diavola at Maialino (Gramercy) – In the sea of Roman pastas and other Italian classics, this is possibly the unsung hero. Heck, after all those years, I needed some help from a reliable insider to discover this gem. The peppery ultra moist beauty comes with a tangy sauce you’ll want to scarpetta the heck out of.
I get cranky when a meal doesnt go my way back at home. I tend to get very quiet, and everyone at the table usually knows it at some point no matter how hard I try to hide it. But when it happens o
What is the perfect base? Its not rocket science. Put your destination stars on the map, and pick something in the middle. The only decision is whether it will be a city, a town, village, or something in the countryside like a villa or Agriturismo. You’ll find many advantages and disadvantages with all options. Thats why mixing it up a little works for many.


Caterina Campodonico was a peasant that worked hard selling necklaces made of nuts and loafs of breads. Before she died in 1882, she was determined to show her legacy by hiring the most expensive sculptor around, Lorenzo Orengo, and a poet to build her monument. In order to do that she had to sell a lot of nut necklaces and save all her profits. So its easy to see why the “Peanut Seller” in the magnificent Staglieno cemetery in Genoa, became a symbol for the hard working people of Genoa. In the pictures below you can see her proudly wearing one of her necklaces.
