10 Best Hotels
Florence’s Renaissance galleries, Siena’s striped cathedral and the hill towns of the Val d’Orcia give Tuscany much of its familiar beauty. Beyond them lie Chianti vineyards, Lucca’s broad city walls and the quieter landscapes of the Maremma. The region also reaches the sea at Argentario and across to Elba, where Portoferraio preserves traces of Napoleon’s exile. Distances matter here: a countryside base near Montalcino serves a different trip from a stay on the coast.
Castiglion del Bosco, A Rosewood Hotel
Montalcino, Italy
Castiglion del Bosco makes the Tuscan estate itself the focus of a stay. Suites occupy the historic borgo, while private villas offer a more secluded rhythm across the surrounding landscape. Wine, dining and wellness give the property depth beyond its views, with Campo del Drago adding a particularly ambitious culinary dimension. Choose it when you want time to settle into one place, combining carefully arranged experiences with long intervals that require no itinerary at all.
A complete estate stay near Montalcino
Castello di Casole, A Belmond Hotel
Casole d’Elsa, Italy
Castello di Casole gives Tuscan country living a polished, expansive setting. The former castle and surrounding estate combine historic stone, carefully chosen furnishings and a variety of suite styles, with an infinity pool and Essere Spa adding to the pleasure of staying put. Dining draws on regional ingredients and the landscape around it. Choose it for a countryside retreat that offers substantial hotel services while preserving a clear sense of the buildings and terrain that shaped it.
Historic country-house character at generous scale
Il Pellicano
Porto Ercole, Italy
Il Pellicano expresses a coastal version of Tuscany, where the rhythm comes from the sea rather than vineyard visits. Above a cove near Porto Ercole, rooms and cottages combine understated Italian style with garden or water outlooks, while the pool and seafront terrace encourage long days on site. Dining and attentive hospitality complete the experience. Choose it for a stay built around swimming, reading and unhurried meals, with the Argentario landscape always close at hand.
Relaxed Mediterranean glamour on Argentario
Borgo Santo Pietro
Chiusdino, Italy
Borgo Santo Pietro makes the relationship between garden, kitchen and hospitality unusually visible. Around a historic villa near Chiusdino, richly furnished rooms and suites open onto an estate of ornamental and productive spaces, with a spa and inviting places to pause throughout. Saporium gives the culinary gardens a refined expression at the table. Choose it for a romantic countryside stay where atmosphere and detail matter, and allow enough time to appreciate the grounds rather than merely pass through them.
A richly detailed garden estate
COMO Castello Del Nero
Barberino Tavarnelle, Italy
COMO Castello Del Nero balances the weight of a historic Chianti castle with Paola Navone’s restrained contemporary interiors. Preserved frescoes and architectural details remain visible, while cool tones and considered furnishings create a calmer atmosphere than a heavily decorated country house. COMO Shambhala adds a substantial wellness dimension, and the estate invites time outdoors. Choose it when you want Tuscan history and landscape with a particularly clear modern design sensibility and an unhurried pace.
Contemporary calm in a Chianti castle
Monteverdi Tuscany
Castiglioncello del Trinoro, Italy
Monteverdi Tuscany turns a stay in Castiglioncello del Trinoro into an encounter with a living hilltop village. Rooms, suites and private houses use local materials and carefully composed contemporary design, allowing stone, light and landscape to shape the atmosphere. Spa facilities and cultural activity add depth to the retreat. Choose it for a quieter, more reflective Tuscan stay, where the pleasure comes from inhabiting the place rather than moving rapidly between famous towns.
Design, culture and village life above the valleys
Il Borro
San Giustino Valdarno, Italy
Il Borro offers several ways to inhabit a Tuscan estate, from suites within the restored medieval village to separate villas and farmhouses. The setting near San Giustino Valdarno gives the stay a strong architectural identity, while wine visits, craft activities and dining introduce different aspects of estate life. Choose the accommodation carefully: the experience can feel intimate and village-centred or more private and independent, depending on where you stay and how you plan to explore.
A restored village with varied estate experiences
Lupaia
Torrita di Siena, Italy
Lupaia keeps the Tuscan countryside experience on an intimate scale. Its rooms and suites occupy restored farmhouse buildings, each with an individual layout and private outdoor space, while the hillside infinity pool creates a natural place to pause. Views extend across the surrounding valleys, with selected suites facing Montepulciano. Choose it for quiet mornings and a strong sense of the landscape, especially when you prefer a personal country-house atmosphere to the breadth of a large resort.
An intimate farmhouse retreat with wide views
Castello Banfi Il Borgo
Montalcino, Italy
Castello Banfi Il Borgo gives wine lovers a particularly coherent base in the Montalcino countryside. Individually designed rooms and suites combine traditional Tuscan materials with polished comforts, while the surrounding vineyards make the estate’s purpose tangible. A pool and inviting shared spaces add time for relaxation between dining and wine experiences. Choose it for a stay that follows the rhythm of one estate, taking the opportunity to understand the landscape rather than simply collect tasting appointments.
A wine-estate stay in Brunello country
La Roqqa
Porto Ercole, Italy
La Roqqa offers a contemporary interpretation of the Tuscan coast. Its rooms use colour drawn from Porto Ercole’s buildings, surrounding vegetation and the sea, while the hotel’s position above the harbour gives the stay a strong sense of place. Rooftop dining and the separate Isolotto Beach Club add different ways to enjoy the setting. Choose it for a design-conscious coastal break that combines town life with time by the water, rather than a remote country-estate experience.
Contemporary design above Porto Ercole