With its rolling vineyards, ochre hills and medieval towns, Tuscany embodies that picture-perfect vision of Italy that keeps on seducing the world. In recent years, the region has seen a rise in wine resorts: elegant estates that combine immersive hospitality, bold architecture and sustainable viticulture. Think biodynamic vineyards at your doorstep, cypress trees framing infinity pools and dinners under vaulted stone ceilings — your courses paired with Super Tuscans or chianti classico. From historic castles to sleek eco-retreats, these estates offer a full-bodied experience of the Tuscan dolce vita — with a generous pour of terroir, tradition and taste. Cin cin.
Editors’ choice
Best for value Castello di Fonterutoli
Best for luxury Rosewood Castiglion del Bosco
Best for green credentials Borgo Pignano
Best for couples Castello di Vicarello
Best for foodies L’Andana
Best for families Castello di Meleto
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1. Casa Newton, Pienza
Mr & Mrs Smith
££ | POOL | Best for design-savvy escapists
Originally built by Gervasio Newton, said to be a descendant of Isaac, this country house in the Val d’Orcia has been transformed by the Bertherat family into a nine-room boutique retreat with serious style. Expect rosemary-blanketed gardens with stunning views over Pienza, rattan lounges, candy-striped pool floats and blush-pink scalloped parasols straight out of a Slim Aarons frame. Inside, it’s all mid-century flair and vintage charm: velvet armchairs, wood-beamed ceilings, and a tactile richness that makes every corner feel considered and sensuous. The two restaurants — Il Cervo, on site, and Ortus, just a stroll away — embrace a strong farm-to-table ethos with the vegetable garden just beyond your table. Don’t miss Fabbrica, the estate’s cool, design-forward winery crafting standout organic wines.
2. Castelfalfi, Montaione
£££ | SPA | POOL | Best for family stays and warm hospitality
This once-abandoned medieval borgo turned 146-key wine resort sits at the heart of a 1,090ha estate of organic vineyards, olive groves and wild woodlands, about 90 minutes southwest of Florence. Acquired by India-born Indonesian tycoon Sri Prakash Lohia and revived with local expertise, it blends global vision and Tuscan soul. The property features two restaurants, a high-end spa and an adventure park to keep children happy. Wine lovers can indulge in the estate’s seven distinct labels, in addition to dozens of activities — from in-house tastings of wine, honey and olive oil to truffle hunts and lake fishing — all offering a full-scale immersion into the Tuscan good life.
3. Conti di San Bonifacio, Gavorrano
kim captein photography
£££ | POOL | Best for organic luxe
When Sarah di San Bonifacio left Goldman Sachs in London to plant seven hectares of organic vines in the Tuscan Maremma, her intention was not to create a wine resort with her husband, Manfredo, but rather a place she and her family could “spiritually detox”. Twenty-odd years later, they have a couple of award-winning Super Tuscans — Docet and Sustinet IGT — to their name, a seven-suite hilltop retreat of impeccable chic (vintage leather chairs, four-poster beds and Asian antiques predominate), and an array of activities to calm even frazzled City types. Private yoga, meditation, ayurvedic massage, mountain biking and truffle hunting are all on the (ethical, sustainable) menu.
4. Villa Bordoni, Greve
££ | POOL | Best for local flavour
This 16th-century patrician villa — the rural residence of a Florentine merchant — deep in Chianti country has lately become not just a culinary destination, but also the progenitor of an excellent cooking school. David Gardner and Catherine Storrar were restaurateurs before deciding to restore the derelict Villa Bordoni and create a boutique hotel (the vineyard, Tenuta di Monte-Ficali, came later). Rustic in style, the cosy bedrooms are big on texture — Baldacchino bed canopies, velvet drapes — as well as charm: ask for the sweet Cappella, in the former chapel. The restaurant, in the original villa kitchens, is gourmet without the fuss: seasonal standouts include an epic bistecca alla Fiorentina and a fine chitarra with a Tuscan ragu.
5. Dievole, Vagliagli
££ | POOL | Best for the light touch
Dievole has been making wine since the year 1090, on and off; today, it has 16 working vineyards across 80 hectares north of Siena. Its latest project, the transformation of an 18th-century hamlet into a luxe wine estate, is, in design terms, an unqualified success. Architect Carlos Hartmann has reimagined Dievole as a creamy dreamscape: ceilings are whitewashed, floors are stone, bathrooms marble, and furnishings and linens the lightest shades of pale. Pops of colour come from the Medici-style still-lifes on the wall. Ristorante Novecento is already making waves, with a menu that majors on seasonal fruit and veg, local cheeses and meats — and, of course, Dievole’s award-winning olive oil.
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6. Rosewood Castiglion del Bosco, Val d’Orcia
£££ | SPA | POOL | Best for all-out luxury
In the heart of the Unesco world heritage site of Val d’Orcia, Castiglion del Bosco may be a 2,023ha working estate producing Tuscan wines of note but, more importantly, it’s also a drop-dead-gorgeous luxury resort. This 900-year-old borgo has been tweaked to World of Interiors standards while retaining a deep sense of place: the 42 suites and 11 villas in restored farm buildings are a model of rustic opulence. Its executive chef creates delicious menus with a focus on terroir, the spa has a luxe line in treatments — and the vines yield 250,000 bottles of Brunello di Montalcino each year.
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7. Castello di Fonterutoli, Castellina in Chianti
£ | POOL | Best for living like a local
There’s a lovely, low-key feel to this medieval village at the heart of the Mazzeis’ chianti classico estate, with 16 simple rooms and suites, plus four traditional apartments, renovated for guests, with vaulted ceilings, terracotta floors, family antiques and spectacular views. They’ve been making wine here for 24 generations — now they’re turning their attention to hospitality, allowing you to live like a local with the added perks of tours and tastings, cooking classes and horse riding on offer. The Osteria offers heritage dishes made with seasonal local produce, focusing on wild game from the estate.
8. L’Andana, Castiglione della Pescaia
££ | SPA | POOL | Best for a summer residence
The Tuscan Maremma is still one of the best-kept seaside secrets outside Italy. Just a ten-minute drive to the coast, rural L’Andana is perfectly placed to enjoy the yacht-club glamour — but run for the hills when the heat is on. La Villa, a former Medici residence where Grand Duke Leopold II summered with his court, has 33 rooms in the main villa, 14 in La Casa, ten at Il Granaio, which can be converted into five two-bedroom apartments, and a four-bedroom private villa with its own swimming pool. They have been reimagined by starchitect Ettore Mocchetti, former editor of AD Italy, to create the kind of refined boho style loved by the cool international crowd. Acquagiusta wines, an Espa spa and the Michelin-starred Trattoria Enrico Bartolini all add up to a super Tuscan experience.
Read our full review of L’Andana
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9. Badia a Coltibuono, Gaiole in Chianti
£ | POOL | Best for blessed peace
This ancient Benedictine abbey has a long history of viticulture: a recent archaeological dig unearthed Romano-Etruscan grape seeds more than 2,000 years old. Today Badia a Coltibuono has four simple apartments and a handful of rooms (formerly the monks’ quarters) in perfect isolation in the Chianti hills. Up here, time stands still — and you can, too. Rest in the shady cloisters, picnic among the vines, and explore the ancient cantinas. Tasting highlights in the wine library include a mellow vin santo; and don’t miss the excellent organic olive oil.
10. Il Borro, San Giustino Valdarno
££ | SPA | POOL | Best for total immersion
When Ferruccio Ferragamo, one-time chairman of the Ferragamo fashion house, took over Il Borro, he described it as a “timeless act of faith”. There’s a sense of total immersion when you pass through the gates of this restored medieval village, a 12th-century stronghold in the upper Valdarno that maintains a strong sense of historical authenticity — albeit sprinkled with Ferragamo fairydust. The style is country chic — natural materials, neutral tones and solid antiques — throughout the 58 suites and three villas. Along with wine tasting, Il Borro offers courses in shoe making and jewellery making; the Vino & Arte gallery has a collection that includes Picasso, Rembrandt and Warhol.
11. Capannelle, Gaiole in Chianti
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£ | POOL | Best for boutique bacchanalia
With just five rooms, this has to be one of Tuscany’s tiniest wine resorts, but three metres beneath the 16th-century villa is a vast nerve centre: a labyrinth of cantinas, tasting rooms and wine libraries carved into the rock. Since 1975, when the estate produced its first label, Capannelle’s ascent has been stratospheric. Above ground, all is peaceful in the elegant gardens, sprawling vineyards and patchwork olive groves. The four bedrooms and one suite are solidly trad — oak-beamed ceilings, tile floors, chintzy furnishings and wrought-iron chandeliers — while the farmhouse breakfasts of home-cured prosciutto, salami, cheese and pastries are epic.
12. Borgo Scopeto, Vagliagli
££ | SPA | POOL | Best for soaking up nature
Borgo Scopeto is a world unto itself. There’s pretty much nothing this wine relais in a pristine 14th-century village north of Siena does not do. Its own line of cosmetics? Check. Beekeeping? Check. Organic vegetables? Check. And of course a range that includes chianti classico, vin santo, grappa and olive oil. Fifty or so rooms are scattered between neatly restored buildings, surrounded by manicured lawns, tennis courts, swimming pools and a spa. Staff can organise not just the usual biking, hiking and riding but go-karting, Nordic walking and vintage car hire too.
13. Castello di Vicarello, Sasso d’Ombrone
£££ | SPA | POOL | Best for Tuscany and beyond
Lost in the Maremma, Castello di Vicarello is an extraordinary place: a 12th-century stronghold that may look like it has leapt from the pages of a fairytale, but inside is a contemporary tastemaker’s dream. Carlo and Aurora Baccheschi Berti worked in fashion, textiles and furniture before bringing their style to bear on what was a crumbling wreck. The ten gorgeous suites are a mix of Indonesian day beds, 1920s Florentine club chairs, eastern art and Persian carpets. Suite Chiesina, with its shaded pergola, is our favourite. The wines of Carlo and his son Brando are gently making waves, while spa treatments showcase the garden’s herbs and flowers.
14. Borgo del Cabreo, Greve
Booking.com
££ | POOL | Best for female forces
Though the Folonari wine estates bear the name of father and son Ambrogio and Giovanni, it’s the women who are the driving force behind this Greve relais de charme. Mamma Giovanna, with the help of daughters Francesca and Angelica, has transformed the borgo’s golden-stone farm buildings into a contemporary 11-room retreat with a rustic edge. Rooms are large and light: whitewashed beams and ivory linens add a sense of refinement, while furniture and artworks are sourced from Tuscan brocantes. This is an oenophile’s dream: spend lazy days tasting eight generations of winemaking experience across the family’s six estates.
15. Poggio Piglia, Chiusi
Booking.com
££ | POOL | Best for style surprises
It may look like a typical Tuscan farmhouse from the outside, but step through the door of the splendidly named Poggio Piglia, midway between Siena and Assisi, for sophisticated surprises. Traditional wooden beams and exposed stone are offset by Philippe Starck furniture, funky lights and contemporary art installations, with whirlpool tubs and four-poster beds in the best of the nine rooms — the result of seven years of work by the Marzeglia family and architect Barbara Spanò. Sample the estate sangiovese and olive oil in the on-site restaurant.
16. Borgo Pignano, Pignano
£££ | SPA | POOL | Best for super-sustainability
An organic oasis 45 minutes from Siena, the Borgo Pignano estate was brought back to life over 20 careful years by Welsh philanthropist Michael Moritz and his wife, Harriet Heyman. It has flourished, becoming a boutique hotel with a collection of simply furnished rooms and apartments — family antiques, faded frescoes, traditional textiles and canopy beds prevail — a pair of restaurants (including the Michelin green-starred Villa Pignano), and two swimming pools. But it is the 303ha of sustainably farmed land of which they are perhaps proudest — and the vines that are now bearing fruit, producing new wines including an excellent Rosso del Guardia red.
Read our full review of Borgo Pignano
17. Castello di Meleto, Gaiole in Chianti
£ | POOL | Best for family fun
Choose from family-sized apartments in the borgo or one of the romantic rooms in this fairytale castle with its roots in the 13th century. It’s a laid-back kind of place with a storybook feel. Child-friendly activities on offer include visits to the bee park and guided cycle rides around Gaiole. Adults can tour the estate in a 4×4 with the resident agronomist, learn to blend their own wine or take yoga classes in the open air. Life feels very simple here: enjoy it.
18. Castello di Ama, Gaiole in Chianti
Alessandro Moggi, courtesy Castello di Ama
£££ | Best for world-class art
Art can be an afterthought even in Italy’s finest hotels. At Lorenza Sebasti’s Castello di Ama, a hilltop hamlet outside Gaiole, installations by some of the greatest contemporary practitioners — Anish Kapoor, Louise Bourgeois, Daniel Buren — are front and centre, along with a world-class chianti classico by winemaker Marco Pallanti. Stay in one of five antique-filled suites in the 18th-century Villa Ricucci, eat on the balcony of the neighbouring Villa Pianigiani and follow the extraordinary art trail, masterminded by San Gimignano’s Galleria Continua, winding in and out of the estate’s 80ha vineyard, down to the wine cellars and into the ancient church.
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