Alluring Tuscany: where to stay to get the most from the region’s vineyards, ancient towns and wild coast
With its gently rolling hills, slender cypress trees and centuries-old villages, Tuscany is one of the world’s most beloved destinations. But beyond the postcard image lies a region of contrasts, from the vineyards of Chianti and wild coastal stretches to ancient spa towns still steaming with mineral springs. A region that has long inspired artists and dreamers, Tuscany has a way of pulling you in gradually, inviting you to savour a glass of wine, wander through olive groves or browse local markets at leisure, a gelato slowly dripping down your hand. Enjoy each destination as a standalone stay, or combine into a glorious itinerary for making unhurried tracks under the Tuscan sun.
Photographs by Kira Turnbull
Lupaia, Torrita di Siena
Of all Tuscany’s scenic landscapes, the Val d’Orcia valley just might be the loveliest. With its sunflower fields, stone farmhouses and hillsides stitched together like a patchwork quilt, this part of the region feels wide open and sublimely serene. Even better, Lupaia, a restored 17th-century farmhouse perched between Montepulciano and Pienza, is one of the most romantic places to bed down in these parts.
The property feels like a tiny hamlet, with suites scattered across old stables and cottages, each one filled with painted beams, velvet armchairs and antique details. With hammocks strung between trees and rosemary brushing the paths, this is a place made for slow afternoons by the pool and long dinners under the stars. In the cooler months, Lupaia’s rustic dining room glows with candlelight and a crackling fire.
Villa di Piazzano, Cortona
A stone’s throw from Cortona — a town that’s long inspired painters, poets and at least one bestselling writer — Villa di Piazzano is a 500-year-old estate that once served as a hunting lodge for a cardinal favoured by the Medicis. Today, it has been reimagined as a country-chic hideaway, with terracotta floors, wood-beamed ceilings and arched windows that let Tuscany’s golden light flood in. With bright rooms spread across former stables, the historic Limonaia building (previously used to store lemons during winter) and an old tobacco tower, you’ll fall asleep immersed in centuries of history. Set within a protected natural reserve, Villa di Piazzano is surrounded by ivy-draped courtyards and terraced gardens planted with thousands of flowers and herbs, with sun-dappled greenery in every direction. You can truly get away from it all here.
La Roqqa, Porto Ercole
A lush, hilly peninsula with echoes of the French Riviera, Porto Ercole remains one of southern Tuscany’s best-kept secrets. Elegant and woodsy, with a smattering of shaded pines and hidden coves, it offers a relaxed kind of coastal glamour beloved by in-the-know Italians who flock here every summer. Perched just above the harbour, La Roqqa is a retro-styled refuge that pays homage to the Italy of the 1960s and 1970s, all sculpted silhouettes, vintage-inspired furniture and bold colour pairings that pop against the aquamarine sea. Spend the day at the hotel beach club, twirling spaghetti alle vongole and sipping a spritz, or hop on a boat to explore nearby islands in the Tuscan archipelago. With the Maremma region on your doorstep, you can also visit local vineyards or go horseback riding with Maremma’s butteri cowboys.
Hotel Lungarno, Florence
Like a refined yacht moored on the banks of the Arno, Hotel Lungarno feels part residence, part floating gallery. It’s the only hotel in Florence built directly over the river, placing you at eye level with the Ponte Vecchio, just steps from the artisan-filled streets of Oltrarno. Owned by the Ferragamo family, the hotel resounds with sartorial flair, reflecting the brand’s roots in exquisite Italian design. Crisp whites and navy blues set a nautical tone, while leather accents keep the atmosphere warm and lived in. With over 400 original artworks lining the walls, including pieces by Picasso and Cocteau, the hotel is also a haven for design and art enthusiasts. In the evening, enjoy a Negroni at Picteau Bistrot & Bar, a riverside cocktail spot with front-row views of the Ponte Vecchio, before enjoying creative dishes at Borgo San Jacopo, the hotel’s Michelin-starred restaurant.
Palazzo Vecchietti, Florence
Tucked just behind Piazza della Repubblica, Palazzo Vecchietti is easy to miss — which is part of its charm. Originally built for a family of wealthy merchants and art patrons, this 16th-century residence still feels more like a private home than a hotel. Step inside and you’ll find countless reminders of the building’s Renaissance past, from sculpted cornices and old fireplaces to an aged stone staircase.
An ideal choice for longer stays, Palazzo Vecchietti’s spacious suites and studios feature hideaway kitchenettes for a little more independence. Breakfast is served daily in an elegant wood-panelled salon or delivered straight to your room. The hotel’s central location — just minutes from the Duomo and Uffizi — means that the city’s best art, culture and trattorias are just a short stroll away.
The James Suite Hotel Firenze 1564, Florence
Intricate woodwork, original stone archways and hand-painted frescoed ceilings coexist with custom-made furniture and muted earth-toned interiors at this noble 16th-century residence turned hotel on Via di Mezzo. Each suite features king-size beds, rare fabrics, curated artworks and views over Florence’s terracotta rooftops.
Villa Petriolo, Florence
Just outside Florence, this honey-hued Tuscan haven can be reached via a 35-minute train ride from Santa Maria Novella to San Miniato-Fucecchio. Villa Petriolo sits on an estate which immerses city breakers in countryside-rooted experiences, including truffle hunting and yoga amid olive groves.
Hotel Regency, Florence
On Piazza Massimo D’Azeglio, this 19th-century villa is brimming with Renaissance paintings, antique mirrors and the scent of lemon trees from its ‘Secret Garden’ oasis. Within minutes, you can stroll to the Duomo, the Uffizi or the Accademia, returning to aperitivi in the garden and nights beneath ornately decorated ceilings of the hotel.
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