There are two ways to spend a day in Cortona. The first way is efficient. You arrive mid-morning, walk Via Nazionale, visit the MAEC museum, take photographs from the main viewpoints, eat lunch at a restaurant near the piazza, browse a few shops, and leave in the late afternoon. You have seen Cortona. You have…
Something has gone wrong with the way most people experience Tuscany. It is not the beauty — the beauty is real, and the region delivers on every expectation in that regard. It is not the food or the wine or the accommodation or the quality of the light in the late afternoon. All of these…
Most visitors to Cortona look up. They climb to the historic center, walk the Etruscan walls on the upper ridge, look out over the Val di Chiana from the height of the hill. The view is extraordinary. The history is visible in every direction. What almost nobody does is look down. Just below the hill…
Florence is not the problem. Florence is extraordinary — one of the densest concentrations of human artistic achievement in the world, a city that justifies every superlative applied to it and earns every visit it receives. The problem is what Florence does to a Tuscany trip when it becomes the entire Tuscany trip. Most visitors…
One day in Cortona is not enough. I want to say that clearly before giving you an itinerary for one day, because the honest version of this guide begins with an acknowledgment that the town rewards more time than most visitors give it. That said — one day, done properly, is enough to understand why…
There are roads in Tuscany that exist in travel photography and roads that exist in real life. Most of the famous ones — the cypress-lined avenue at San Quirico d’Orcia, the Gladiator road in Val d’Orcia — are both. They are genuinely beautiful and they are genuinely crowded, particularly in the hours when the light…
Montepulciano is one of the great wine towns of Italy. Not great in the way that Barolo is great — remote, specialized, requiring pilgrimage. Great in the way that a hilltop town can be when everything about it — the architecture, the people, the landscape, the thing it produces — has been organized around a…
There is a specific moment that happens on group tours that most people recognize but rarely articulate. You are standing somewhere beautiful — a vineyard, a hilltop viewpoint, a medieval piazza — and you are surrounded by twenty other people who are also standing there, also looking, also photographing. The guide is speaking into a…
There is a specific problem with corporate gifting that nobody in the corporate gifting industry wants to acknowledge. The gifts do not work. Not because they are low quality — many are not. Not because the recipients are ungrateful — most are perfectly polite about it. But because a gift that could have been given…
In 1996, an American professor named Frances Mayes published a memoir about buying and restoring a derelict farmhouse on a hillside above Cortona, a small Etruscan hilltop town in southern Tuscany that most people outside Italy had never heard of. The book was called Under the Tuscan Sun. It sold millions of copies. It was…