Boutique Hotels in Tuscany

Tuscany is bigger and more varied than the postcard implies, and picking the right corner is the most important decision in planning a trip here.

Chianti is what most first-timers picture — the rolling hills between Florence and Siena, vineyards, cypress alleys, hilltop villages. The most photographed Tuscany, and the busiest. The Val d'Orcia runs south of Siena into the crete senesi, the chalky clay badlands that frame the abbeys of Sant'Antimo and Monte Oliveto Maggiore; this is Brunello di Montalcino country, quieter than Chianti and with the strongest light.

The Maremma is the southern coast and its inland hills — wilder, less postcard, the Tyrrhenian visible from the higher ground and an agricultural rhythm largely unchanged for centuries. The Mugello sits in the Apennine foothills directly north of Florence, proper countryside an hour from the city, the Medici family's original home ground. And the Versilia is the north-western coast below the marble Apuan Alps — beaches, the sculptors' town of Pietrasanta, and hills that look down to the sea. Pick one, stay put, and let it unfold.

The hills south-west of Siena run through pilgrim country. The medieval Via Francigena from Canterbury to Rome cuts diagonally through, with the Cistercian abbey of San Galgano — the roofless Gothic church with the sword in the stone — as its 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 medieval estate that the Danish couple Jeanette and Claus Thottrup bought as a ruin in 2001, restored over seven years, and opened in 2008. Around twenty rooms, hand-frescoed and antique-furnished, no two alike, sit within a 300-acre working organic farm — vegetables from the kitchen garden, cheese made each morning at the dairy from the estate's own sheep, honey from its bees. Chef Ariel Hagen runs the starred Saporium kitchen, while the second restaurant, Trattoria Sull'Albero, is built around the boughs of an ancient oak. The estate served as a lazzaretto, a pilgrim hospice, for travellers bound for San Galgano eight hundred years ago — and something of that restorative purpose persists.

The southern coast and its inland hills carry a different feel from the famous wine country to the north — wilder, less Chianti-postcard, with the sea visible from the higher properties and a pace barely changed in centuries. Montalcino and the Etruscan tufa town of Pitigliano are the inland landmarks; the Argentario promontory is the beach.

Castello di Vicarello sits on a Maremma hilltop near Poggi del Sasso, midway between Rome and Florence — a 12th-century castle, once a fortress of the Republic of Siena, that Carlo and Aurora Baccheschi Berti found as a ruin in the 1980s and restored over more than a decade, opening in 2003. The forty-hectare estate produces the family's own organic wine and olive oil. There are ten individually designed suites and a two-bedroom villa, furnished with the art and antiques the family gathered over decades of travel, and two marble pools — a travertine infinity pool over the valley and a green-marble wellness pool in the olive grove. Rooftop dinners run by candlelight. Fifty minutes to Siena, an hour to Montalcino, an hour to the coast.

The Apennine foothills directly north of Florence are the agricultural Tuscany that wine-country travellers miss. This was Medici home ground — Cosimo the Elder bought land here in 1420, and the family's earliest castles, Cafaggiolo and Trebbio, stand nearby. The hills are gentler than the Val d'Orcia, the towns smaller and less filtered, the food closer to the source.

Tenuta Le Tre Virtù occupies a farmhouse, the Casaccia, found as a ruin in 2010 by Valentina and Christian, who restored it and reopened it as a small relais in 2016. Seven individually styled rooms, each with its own colour and scent and handcrafted majolica, sit within a certified-organic farm of around six hectares — fruit trees, young olives, a kitchen garden and a vineyard planted in 2020. The kitchen, under chef Antonello Sardi, holds a Michelin star and a green star for sustainable cooking. The whole estate can be booked entire, and the Convento di Bosco ai Frati, among the oldest in Tuscany, is a short walk away. An hour from Florence.

The Versilia is Tuscany's north-western shore, where the marble Apuan Alps drop towards the sea. It is two things at once: the beach clubs of Forte dei Marmi and Viareggio along the coast, and behind them the sculptors' town of Pietrasanta, a centre for marble and bronze since the nineteenth century, with the Carrara quarries — where Michelangelo chose the stone for the Pietà — rising beyond.

Locanda al Colle sits on a hill above Camaiore, five kilometres back from the coast, with the sea on one side and the marble mountains on the other. The owner, Riccardo Barsottelli, spent two decades in fashion before turning this farmhouse into a guesthouse that pointedly refuses the word hotel — no reception desk, no counter, just twelve individually styled rooms, vintage and Art Deco finds gathered across Paris, London and Buenos Aires, and a rotating collection of contemporary art and Pietrasanta sculpture throughout. A salt-water pool sits among the olives; the chef cooks dinner for resident guests a few nights a week; a private beach club is arranged at Marina di Pietrasanta. Open late March to early November.

The hills south-west of Florence, running towards Volterra and the Maremma, are a lesser-photographed Tuscan wine zone. The medieval village of Castelfalfi sits at their heart, near Montaione — an entire borgo, gathered around a castle and a 13th-century church, restored from its medieval bones as a working estate.

Toscana Resort Castelfalfi is the larger-scale option in our Tuscany collection: the restored village itself, reopened in 2024, with around 140 rooms across a main hotel and the historic Tabaccaia, private villas, several restaurants, a 27-hole golf course and the estate's own organic winery and oil. The point of it is the integration with a living medieval village rather than the single-restored-country-house model that defines most of the region. It suits travellers who want estate-scale facilities — the golf, the RAKxa spa, the choice of kitchens — alongside the rural Tuscan setting, and it makes a natural base for Florence, Pisa, Siena, Volterra and San Gimignano alike.