Boutique Hotels in Tuscany

Tuscany is bigger and more varied than the postcard implies. Picking the right sub-region is the most important decision in planning a Tuscan trip.

Chianti is what most first-time visitors picture — the rolling hills between Florence and Siena, vineyards, cypress alleys, hilltop villages. The most photographed Tuscany; also the busiest.

The Val d'Orcia runs south of Siena into the crete senesi — the chalky white-clay badlands that frame the abbeys of Sant'Antimo and Monte Oliveto Maggiore. Brunello di Montalcino country. Quieter than Chianti, with the strongest light.

The Maremma is the southern Tuscan coast and its inland hills — wilder, less postcard, with the Tyrrhenian Sea visible from the higher properties and an agricultural rhythm that's run unchanged for a thousand years. Argentario beaches, Pitigliano's Etruscan tufa cliffs, Montalcino at the inland edge.

The Mugello sits in the Apennine foothills directly north of Florence — proper Tuscan countryside an hour from the city, with the original Medici villas (the family was from here before moving south), the Mugello motor-racing circuit, and a slower register than the famous wine country south.

The hills south-west of Siena run through pilgrim country. The medieval Via Francigena from Canterbury to Rome cuts diagonally through here, with the Cistercian Abbey of San Galgano — the roofless Gothic church with the sword in the stone — as the area's pulled-from-legend centrepiece. Quieter than Chianti, less photographed than the Val d'Orcia.

Relais Borgo Santo Pietro is the most ambitious property in our Tuscany collection — a 13th-century estate that the Danish couple Jeanette and Claus Thottrup bought in 2001, restored over seven years, and opened in 2008. Twenty-two rooms, hand-frescoed, antique-furnished, no two alike. The 300 acres are a working organic farm: vegetables from the kitchen garden, cheese made each morning at the on-site dairy from the estate's sheep, honey from the estate's bees. Ariel Hagen runs the Michelin-starred Saporium kitchen; the second restaurant, Trattoria Sull'Albero, is built around the spreading boughs of an ancient oak. The estate served as a lazzaretto — medieval pilgrim hospice — for travellers on the Via Francigena heading to San Galgano in the thirteenth century.

The southern Tuscan coast and its inland hills carry a different register from the more famous wine country to the north — wilder, less Chianti-postcard, with the Tyrrhenian Sea visible from the higher properties and a pace that's run more or less unchanged for centuries. Montalcino and Pitigliano are the wine and Etruscan anchors inland; the Argentario promontory the beach destination.

Castello di Vicarello sits on a Maremma hilltop near Poggi del Sasso, midway between Rome and Florence — a 12th-century castle that Aurora and Carlo Baccheschi Berti restored across eighteen years from the 1980s. The forty-hectare estate produces the family's own organic red wine and olive oil. Seven rooms and suites, hand-curated with art and antiques the family collected over decades of global travel. The infinity pool faces the open countryside; rooftop dinners run by candlelight under the Tuscan stars. Fifty minutes to Siena, an hour to Montalcino, an hour to the coast.

The Apennine foothills directly north of Florence are the agricultural Tuscany the wine-country travellers miss. The Medici family's original villa di villeggiatura estates are here. The hills are gentler than the Val d'Orcia, the towns smaller and less filtered, the food traditions closer to the source.

Tenuta Le Tre Virtù occupies a Mugello hamlet found abandoned in 2010 by Valentina and Christian, who restored the original Casaccia farmhouse and its outbuildings — the original barn, cottage, and pigsty — into a seven-suite intimate retreat. The kitchen is Antonello Sardi's Virtuosino Bistrot, with both a Michelin star and a Michelin Green Star for sustainability. The estate runs e-bike tours of the surrounding hills, truffle hunting in season, and a vineyard wine programme. An hour from Florence.

The Val di Cecina south-west of Florence is the lesser-photographed Tuscan wine zone, running into the Maremma coastal hills. The medieval village of Castelfalfi sits at its heart — continuously inhabited since the eighth century, now restored from its medieval bones as a working agricultural estate.

Toscana Resort Castelfalfi is the larger-scale option in our Tuscany collection — the restored village itself, with two hotels (Il Castelfalfi and Hotel La Tabaccaia), private villas, two restaurants, an eighteen-hole golf course, and the estate's own wine production. The editorial point is the integration with a continuously inhabited medieval village rather than the more typical single-restored-country-house model. Suits travellers who want estate-scale facilities (the golf, the spa, the multiple dining options) alongside the rural Tuscan setting.