Anders Overgaard
Ferenc Máté

The biggest drawback to traveling is that you can’t take your cozy home with you. Tuscany’s boutique hotels have changed that. Welcoming, comfy, small (almost always less than 20 rooms), they spoil and coddle you. The ones I listed are of superb quality and have meticulously thought out, yet elegantly understated décor. The locations, whether in town or country, are simply the best. In the country, the views are usually breathtaking, the silence deafening. In towns, the settings as charming as can be. Their public spaces are welcoming, their art and architecture mostly minimal, but unforgettable. The service? Like you wish your mother’s had been at her spoiling best. Each hotel reflects the passion and vision of its owner. Admittedly, boutique hotels are pricey but then you’re only staying a few nights, not the rest of your life, although you’ll wish you could. Their biggest drawback: you’ll be tempted to hang out in their lounges, pools, and gardens day and night, and may never actually get to see Tuscany. But then there’s always the next time.

JK Place, Florence

This is in a dream location—the now all-pedestrian and flower-strewn Piazza Santa Maria Novella, right across from the magnificent church whose interior walls are covered with Ghirlandaio frescos and monastery, the fascinating twelfth-century pharmacy. The nineteen-room hotel is in a completely redone fifteenth-century palazzo. Its reception area is a book-filled drawing room. You don’t feel like you’re checking in: you think you just arrived at a friend’s for a drink.  The lounges are intimate, as is the bar and the restaurant, part of which is a covered terrace jutting  into the piazza. Breakfast is served in an atrium full of fresh flowers. The rooms have marble baths and sheets of linen. The quality of everything is superb. And there is a romantic rooftop lounge for starry nights.  Claudio Meli, the hotel’s director has a well-articulated approach: “I have two children. The hotel is my third.“

La Bandita, Pienza

This is the ultimate two-fer offering nine rooms in a hilltop villa in utter isolation, and just a few miles away, eleven rooms in a converted monastery in the heart of a medieval town where you can experience the village life of Tuscany. The Villa, set on its own hill, is in the middle of the UNESCO World Heritage Valley of the Orcia River. Each room has one of the best views in Tuscany. There is a stunning, double-infinity pool, friendly outdoor spaces, and silence. There are very social indoor and outdoor dining rooms. Gorgeous baths. The Townhouse has a tranquil garden and its own excellent restaurant. The architect has respected the ancient building—one room has the original marble altar of the prayer room—but added minimalist modern touches. Medieval Zen Modern. And the town, Pienza, is the idyllic medieval town. 

Villa Bordoni, Chianti

For centuries the world has been in love with the Chianti Hills. Close to Florence and not far from Siena is the region’s most famous town, Greve. High in its silent pine and cypress-covered hills, is a thoughtfully restored fifteenth-century villa. It has nine rooms, each named after the distant castle it faces. It has classic furnishings, ultra-modern baths, and charming common spaces. The lush gardens—one part formal Italian, the rest olive-filled rustic hillside—has many private corners on various levels, where you can dream away the hours. There is a hidden, tranquil pool, and a rare, romantic restaurant with excellent food, a wonderful wine cellar and perfect service. Not only do they offer classes in Tuscan cooking, but they even take you on truffle hunts (autumn). Then the chef prepares the truffles for you. Heaven.

Monteverdi

In a world of its own. You literally and uniquely insert yourself into the life of the living twelfth-century stone hamlet of Castiglioncello del Trinoro. High in the fresh-air of summer nights—at 2,400 feet— a twenty-room hotel dots the streets, alive with 14 full time inhabitants—many of whom seem from central casting—with their welcoming Tuscan faces and comfortable Tuscan pace. The hotel is spread though the town: some rooms in various houses, the restaurant dug into the rock of the hill, the enoteca and bar perched over the valley. All rooms have spectacular interior design: Elegant Monastic. There is a hilltop pool set in a garden, with eagles-only views. Every detail is quality plus. Bedrooms and baths of your dreams. Vast range of accommodations from single to six-bedroom villas. The restaurant run by the irresistible Giancarla Bordoni uses “the best, freshest and most savory ingredients in the world.” The dishes she turns them into are amazing.

They also have cooking classes and artists in residence. Does more exist?

Il Pellicano

Truly legendary, having hosted the likes of Jackie Onassis, Il Pellicano boasts one of the most spectacular locations on the Mediterranean Sea. A few miles from the ancient and charming old fishing port of Porto Ercole on the Argentario Peninsula, it has the crystal-clear sea below and a Spanish fortress above. Its thirty-nine rooms are dispersed in various cottages and villas. There’s a heated saltwater pool carved from the rock, privacy, views, and absolute discretion. And sunrises to die for, storms even better. Perched in a cove with a private beach below, it was started as a love nest that expanded into an unforgettable hotel with one of Italy’s best restaurants—two Michelin stars—with dishes that astonish the eye and the palate. Splurge: you only live once.  

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