The best luxury hotels in Tuscany - our personal selection
Published 03 June 2026
Our best hotels in Tuscany and reasons why we have selected them
Ask anyone who has been to Tuscany what they remember most, and they will not usually begin with a museum or a wine list. They begin with a place: a hotel that felt exactly right for where it was, a room with a view that made the landscape feel personal, a terrace where the evening light on the hills changed everything. The hotel is the lens through which Tuscany is experienced.
At Expressions Holidays we have been designing tailor-made holidays to Italy for over 35 years. Our Tuscany portfolio is not a list compiled from aggregator ratings. These are hotels we know personally — properties our consultants have visited, whose owners and managers we have met, whose food and service and position in the landscape we can speak to with confidence. This is our honest selection.
Marcelle Hoff, owner and joint managing director says 'The question we always ask ourselves is whether we would book a client into this hotel without hesitation. Every hotel in this selection passes that test'.
COMO Castello del Nero, Chianti — a 12th-century castle between Florence and Siena
Castello del Nero is among the most complete expressions of Tuscan luxury currently available. The 12th-century castle sits at the centre of a 740-acre estate of olive groves and vineyards in the Chianti hills, precisely equidistant between Florence and Siena — thirty minutes from each by car. The 50 rooms and suites are individually furnished, many with original 18th-century frescoes, and the estate's sense of accumulated history is present throughout without tipping into museum-like formality. The Michelin-starred restaurant La Torre draws on the kitchen garden and estate produce; there is also a more casual trattoria and al fresco pavilion dining for warmer months. The Asian-inspired spa, heated outdoor pool and several kilometres of marked walking routes around the estate mean that clients rarely feel the need to leave. For those who do, wine and olive oil tastings in the 12th-century cellar are among the more memorable food experiences we offer in Tuscany.
L'Andana, Maremma — a grand duke's estate reimagined
L'Andana began as the summer residence of Grand Duke Leopold II of Tuscany. The setting — extensive grounds of umbrella pines and olive trees a couple of miles from the southern Tuscan coast — still carries the unhurried grandeur that the original occupant presumably intended. The 33 rooms are finished in the earthy colours of the Maremma: terracotta, ochre, warm linen. The main restaurant, La Trattoria Enrico Bartolini, holds a Michelin star and focuses on the produce of the coastal hinterland. Activities — golf, cycling, wine tastings, fitness classes — are woven into the estate rather than bolted on. L'Andana is ideally positioned for clients who want a fixed base in southern Tuscany: the coast, the Etruscan sites, the hill towns of Pitigliano and Sorano, and the thermal springs of Saturnia are all within reach.
Borgo Scopeto, near Siena — a 14th-century estate with Siena on the horizon
Borgo Scopeto occupies a restored 14th-century stone hamlet in the Chianti Senese hills, with a view across vineyards and rolling countryside to the Mangia Tower and Siena's cathedral visible in the distance. It is a five-star property with 58 rooms and suites, all different, many with the original wooden-beamed ceilings and terracotta floors of the historic buildings. The La Tinaia restaurant is set in the old estate cellars and serves Tuscan dishes alongside wine and olive oil produced on the Borgo's own estate. Three pools — including a saltwater and a heated option — and a full spa give the property strong appeal for clients who want to divide time between the landscape and the resort. Siena is twenty minutes away; the Chianti wine zone surrounds it. Borgo Scopeto suits clients who want the character of a genuine historic settlement without sacrificing the facilities of a well-run modern hotel.
Castello di Velona, Montalcino — hilltop thermal spa and Brunello on the doorstep
The Castello di Velona occupies a medieval fortified hilltop above the Val d'Orcia, with views across olive groves and forests to the distant profile of Monte Amiata. It is a five-star property built from the ruins of a historic settlement, with 45 rooms and suites furnished in Tuscan country style — stone, dark wood, warm textile. What distinguishes it in the Tuscan luxury market is the combination of spa and wine. The thermal spring water at Velona flows at 50 degrees, the hottest in Tuscany, supplying five indoor and outdoor pools and running directly from the bath taps in the suites. The hotel also produces its own Brunello di Montalcino and Rosso di Montalcino from estate vineyards. For clients whose primary interest is the wines of southern Tuscany, the position — directly above the Montalcino wine zone — is unmatched.
Castel Monastero, Chianti Senese — a medieval village resort with serious ambition
Castel Monastero is built around the piazza of a genuine medieval village in the Chianti Senese hills south of Siena. The 74 rooms and suites are furnished in the local idiom — stone, barrel vault, dark beams — and the estate covers four hectares of vineyard and woodland. At the centre of it all is the Contrada restaurant, opening onto the village piazza in a way that makes the resort feel lived-in rather than constructed. Activities range across wine tastings, truffle hunting, cooking courses, tennis and golf, and the spa is among the most comprehensive in the Chianti area. Castel Monastero works particularly well for clients who want to base themselves in a single property and absorb southern Tuscany gradually: Siena is thirty minutes away, the pilgrimage road of the Via Francigena passes nearby, and the hill towns of the Crete Senesi — Asciano, Buonconvento, San Quirico d'Orcia — are within easy reach.
How to choose the right hotel for your Tuscany holiday
The hotels above serve different purposes and suit different clients, and we never recommend one over another without understanding what a holiday in Tuscany is actually for. A client who wants to walk into the vineyards before breakfast needs a different property from one who wants a coastal retreat. A couple celebrating an anniversary on the Argentario has different requirements from a family with older children looking for a base near Cortona. These are conversations worth having before a hotel is booked. The difference between the right property and a merely good one is often the difference between a holiday that feels accidental and one that was made for you. Speak to us as you plan your Tuscan holiday.
Every Tuscany holiday we design is built around the specific brief — the region you want to focus on, the hotel that fits the occasion, the itinerary that connects the places in the right sequence. The sample itineraries on our Tuscany page are a starting point for a conversation rather than a fixed product.
To begin planning, call us on 01392 441245 Monday to Friday 9am to 5.30pm, Saturday 10am to 2pm, or email info@expressionsholidays.co.uk.
