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Most people planning a trip to Tuscany start with a single image in mind: a cypress-lined road, a glass of red wine, a stone farmhouse on a hill somewhere between Florence and Siena. That image isn’t wrong, but it’s incomplete.
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Every wine-focused corner of Tuscany seems to get slotted into a hierarchy sooner or later, and Montepulciano has spent decades sitting just below Montalcino in that pecking order — “the other big red town,” the one people visit second, after Brunello.
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Of all the hill towns scattered across Tuscany’s wine country, Montalcino occupies a category of its own.
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Ask a wine-focused traveler about Chianti and nine times out of ten they mean Chianti Classico, the famous black-rooster zone stretching between Florence and Siena. Fair enough — it earns the attention.
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Say the word “Chianti” to most travelers and you’ll get a vague image: a straw-wrapped bottle on a red-checkered tablecloth, maybe a rooster logo they half-remember from a wine list.
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Long before wellness retreats and fitness influencers made “movement” a lifestyle buzzword, Lake Como’s elite were already living it.
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Sicily does not do luxury the way the rest of Italy does. There is no single postcard address here, no one town that carries the island’s entire reputation for beautiful stays, the way Positano does for the Amalfi Coast or Portofino does for Liguria.
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Staying Connected Abroad: The Ultimate eSIM Guide for the Modern Luxury Traveler There is a particular kind of frustration reserved for the traveler who has just landed somewhere extraordinary, whether…
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Sicily’s coastline runs for over 1,000 kilometres, and almost none of it looks the same twice.
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June 2026 · Charlotte Hill Why Taormina is the most compelling town in Sicily – and why the most discerning travellers, wine lovers, yacht crews, and property investors keep coming back.