Best hotels in Tuscany, Italy | A Curated Visual Guide to Top Stays

Welcome to PressBeyond, the ultimate curated visual guide for design-driven hotels! My name is Will Miller and these are my recommendations for the best boutique and luxury hotels in Tuscany, Italy.

I am the founder of PressBeyond and I am an ultra-meticulous hotel curator who loves clean visuals. I have individually analyzed and tiered each hotel included in this guide based on a variety of criteria (architecture & design, location, brand & brand affiliation, existing reviews, and my own personal experiences), and importantly, I have hand-selected the leading imagery for each hotel to provide you with easily-digestible, yet detailed and complete, like-for-like, high-level visual profiles. I felt this summarization step was a critical missing piece across existing guides, blogs, and booking platforms. My aim is to make it easier for people to identify hotel environments that resonate with them, along with enabling them to visualize the types of social experiences that those environments help foster. My brain doesn't work when exposed to cluttered content, so my goal was to create the opposite.

Underneath this, we are also a full booking engine offering 5% Venmo cash back along with other exclusive perks. For all of you design-obsessed hotel enthusiasts out there, I hope this guide helps get you to where you see yourself!

An Overview of the Boutique & Luxury Hotel Landscape in Tuscany, Italy

The most clarifying thing you can learn about Tuscany's accommodation geography is that it has almost nothing to do with cities. Siena matters, certainly — the Grand Hotel Continental, installed in a 17th-century palazzo on the Banchi di Sopra, offers a kind of gilded civic experience that the countryside cannot replicate — but the real argument here is made in stone farmhouses, medieval borghi, and converted estates strung across the hills. The question is not which town to base yourself in but which landscape, and that choice carries substantial aesthetic and experiential consequences. Val d'Orcia sets the highest formal standard in the portfolio. Rosewood Castiglion del Bosco, a restored Brunello estate with interiors shaped by an editorial eye for Tuscan materiality — terracotta, rough linen, reserve-aged oak — occupies nearly 4,000 acres and operates as though hospitality were incidental to the farming. Monteverdi, in the nearly abandoned hilltop village of Castiglioncello del Trinoro, took a different approach: architect Edoardo Milesi worked with a collection of derelict medieval structures and turned them, with deliberate restraint, into something closer to a contemporary arts residency than a resort. The contrast between these two defines a genuine tension running through the whole region — conservation-as-luxury versus intervention-as-design statement. Castello di Vicarello in the Maremma pushes furthest toward the latter, its remote location and singular aesthetic making it the choice least legible to hotel conventions of any property in this group. The Chianti corridor and its fringes provide a middle register between those extremes. COMO Castello del Nero, a 12th-century castle above the Pesa Valley, has the bones of a great architectural property and the COMO group's reliable calibration of calm. Borgo San Felice, a self-contained medieval hamlet near Castelnuovo Berardenga, sustains an agricultural integrity that larger operations often sacrifice for amenity. For travelers willing to cross into Umbria, Castello di Reschio — restored under the vision of Count Benedikt Bolza, who trained as an architect and oversaw an obsessive decades-long reconstruction — is arguably the finest single act of rural estate design in central Italy, and worth the conceptual border crossing from Tuscany proper. The range across all of these properties is enormous in price and philosophy, but the through line is constant: here, the building is always the story.

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Villa Petriolo

Tuscany, Italy • Cerreto Guidi • OPTIMIZE

avg. $253 / night

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Hilton Honors™ property

Villa Petriolo Design Editorial

Somewhere between Empoli and Cerreto Guidi, where the Arno valley flattens into vine rows and silver-leaved olives before the hills rise again toward San Miniato, a seventeenth-century Tuscan farmstead complex was converted into Villa Petriolo with the particular conviction that the building's agricultural bones — its lime-washed walls, terracotta floors, and barrel-vaulted cellars — deserved to survive the renovation rather than be smoothed away. From the air, the compound arrangement of the main villa and flanking cascine is immediately legible: the pale ochre render of the central building, the cypress sentinels marking the entrance court, the vineyards pressing in from three sides. The infinty pool, positioned to frame an unbroken prospect across undulating wheat fields toward a hilltop town on the horizon, makes that agricultural landscape the property's primary amenity. Inside, the interiors calibrate carefully between restoration and invention. Bedroom ceilings expose their original chestnut beams, the plasterwork left deliberately rough and mineral in tone — the grey-green marmorino finish giving walls an aged patina that no decorator could convincingly fake. Against this, the furnishings introduce a considered modernity: forged iron four-poster beds with brass finials, upholstered bench seats in dove-grey linen, freestanding roll-top baths positioned as room centerpieces rather than hidden behind doors. The restaurant, fitted into a vaulted cantina, pairs exposed Roman brick arches with copper pendant lighting and polished steel bar joinery — a combination that honors the bones of the agricultural building without pretending the twenty-first century hasn't arrived.

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L'Andana Resort

Tuscany, Italy • Grosseto • SPLURGE

avg. $509 / night

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LHW Leaders Club property

L'Andana Resort Design Editorial

Napoleon Bonaparte's brother-in-law, Félix Baciocchi, built the estate at Tenuta La Badiola in the early nineteenth century as an imperial hunting retreat, and the terracotta-roofed villa that anchors L'Andana today carries that provenance with considerable ease. Seen from above, the salmon-pink palazzo rises from the flat agricultural plain of the Maremma near Grosseto — vineyards pressing close on three sides, stone pines and Italian cypresses drawing a formal perimeter — with the authority of a building that was always meant to command its landscape rather than defer to it. Alain Ducasse brought the estate back to life in 2004 when he converted it into a relais with around thirty rooms, and the restaurant La Trattoria Enrico Bartolini has since become the gastronomic anchor for the whole southern Tuscan coast. Inside, the interiors lean into the character of the original fabric rather than smoothing it away. Rooms are dressed in Venetian-plaster walls washed to a warm amber, wide-plank oak floors, and carved baroque headboards upholstered in deep red or lacquered in silver-leaf white — furniture that draws on Italian eighteenth-century decorative traditions without tipping into pastiche. The restaurant preserves exposed handmade brick columns and barrel-vaulted ceilings finished in the same terracotta tile visible across the roofline, a glazed wine library set flush between the columns as an unabashedly contemporary intervention. The pool terrace, framed by stone-paved lounging decks and garden borders thick with Mediterranean planting, pulls the building's warm ochre facade into easy conversation with the Maremman sky.

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Il Borro

Tuscany, Italy • Arezzo • OVER THE TOP

avg. $730 / night

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Il Borro Design Editorial

A medieval hamlet in the Valdarno hills above Arezzo, rescued from near-ruin by Ferruccio Ferragamo in the 1990s, gave Il Borro its defining character before a single design decision was made. The Ferragamo family acquired the entire borgo — stone houses, church, mill, and surrounding vineyards — and embarked on a restoration that preserved the settlement's agrarian bones while threading in the quiet comforts of a luxury relais. The result is a property spread across multiple structures rather than concentrated in a single building: ochre-rendered farmhouses sit beside ancient stone walls, terracotta roof tiles weather identically whether they date from the fourteenth century or were laid thirty years ago. The interiors across the guest rooms honour that layering without forcing it. Exposed timber ceiling beams, some painted white and others left in their raw honey-coloured state, anchor rooms furnished with striped upholstered armchairs, botanical prints in dark frames, and walnut writing desks — the atmosphere closer to an inherited country house than a curated hotel. Working fireplaces appear in several rooms, and terracotta floors run through much of the older accommodation. Where contemporary additions were necessary — most visibly in the spa pavilion and restaurant, where full-height steel-framed glazing opens onto views over the valley — the intervention is deliberate and confident, exposed brick piers and polished concrete floors placed in direct conversation with the landscape beyond.

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Villa di Piazzano

Tuscany, Italy • Cortona • OVER THE TOP

avg. $830 / night

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Villa di Piazzano Design Editorial

A fifteenth-century Medici villa set among cypress allées in the Valdichiana hills between Cortona and Lake Trasimeno, Villa di Piazzano carries its age with the kind of unforced confidence that centuries of continuous habitation tend to produce. The property — a manor house flanked by stone-roofed agricultural outbuildings arranged around terraced gardens — was converted into a small hotel by the Cotarella family, who brought the same careful stewardship they apply to their winemaking across central Italy. The aerial view confirms the logic of its layout: the villa at centre, symmetry enforced by flanking cypresses, the rectangular pool cut into the lower terrace in a way that feels like an extension of the formal garden rather than a modern intrusion. Inside, the rooms divide clearly between two registers. The grander suites in the main villa feature arched pietra serena window surrounds, linen curtains with pom-pom trim in duck-egg blue, Persian rugs over wide-plank oak floors, and painted panelling — the atmosphere closer to a Florentine patrician house than a converted farmhouse. The restaurant gathers around a monumental stone fireplace dated 1402, its heraldic fire screen anchoring walls finished in pale intonaco plaster with shallow corniced panels. The converted outbuilding rooms are quieter in register, with limewashed beams, cherry-wood credenzas, and linen drapes admitting the particular greenish Umbrian light that floods the valley all summer.

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Borgo San Felice

Tuscany, Italy • Siena • OVER THE TOP

avg. $921 / night

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Borgo San Felice Design Editorial

Scattered across a hilltop in the Chianti Classico wine country between Siena and Florence, a genuine medieval hamlet — complete with its own Romanesque chapel, stone farmhouses, and ancient olive press — was converted into Borgo San Felice rather than merely restored to one. The distinction matters: the property functions as a small village of 57 rooms and suites distributed across multiple buildings, their exteriors left in the weathered pietra serena and rough-cut travertine that centuries of Tuscan agriculture deposited there. Stone archways, terracotta roof tiles, and the fourteenth-century chapel of Sant'Appiano anchor the arrival courtyard, visible in the images at dusk with Italian stone pines casting long shadows across the gravel piazza. Inside, the rooms move between two registers. The grander suites reveal exposed chestnut roof beams over wide-plank oak floors, walnut headboards set into arched brick recesses, and upholstered armchairs in houndstooth — a quietly contemporary intervention that honours the structural fabric without dressing it in period costume. Simpler rooms take a fresher approach: painted horizontal stripe walls in dove and cream, velvet tub chairs in dusty blue, curtains banded with embroidered trim in cardinal red. The restaurant terrace, framed by old brick piers and shaded by cream canvas parasols, looks out over the cypress-lined garden toward the Chianti hills — a view so composed it seems almost arranged, though the landscape arrived long before the hotel did.

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Monteverdi Tuscany

Tuscany, Italy • Val d'Orcia • OVER THE TOP

avg. $1,002 / night

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Monteverdi Tuscany Design Editorial

Perched above the Val d'Orcia on a hillside outside Castiglioncello del Trinoro, a medieval hamlet that had stood largely abandoned for decades became, under the direction of American collector and cultural entrepreneur Michael Cioffi, one of the more quietly influential small hotels in Tuscany. Monteverdi Tuscany opened in 2013 after a painstaking restoration of the village's stone farmhouses and agricultural buildings, with New York-based designer Ilaria Miani guiding the interiors toward something closer to an inhabited village than a conventional hotel. The 18 rooms and suites distributed across multiple structures draw their character directly from the bones of the buildings: original chestnut ceiling beams left exposed overhead, rough-hewn stone walls sealed rather than plastered over, and antique terracotta and wide-plank oak floors preserved wherever possible. What distinguishes Miani's approach is the deliberate tension between the ancient and the frankly contemporary. One room deploys a bed frame mounted on industrial castors beneath those age-darkened beams, paired with woven armchairs in grey wool and terracotta-red poured resin floors; another settles deeper into the vernacular, with linen the colour of pale wheat, jute kilim runners, and a blackened steel fireplace as the room's sole modern note. The dining room cuts into the living rock face of the hillside, its rough stone wall left entirely bare. Outside, a flagstone terrace furnished with Jorge Ferrari-Hardoy butterfly chairs surveys the Val d'Orcia rolling south toward Monte Amiata — the view as elemental as anything inside.

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Castello Di Casole, A Belmond Hotel, Tuscany - Image 1

Castello Di Casole, A Belmond Hotel, Tuscany - Image 2

Castello Di Casole, A Belmond Hotel, Tuscany - Image 3

Castello Di Casole, A Belmond Hotel, Tuscany

Tuscany, Italy • Siena • OVER THE TOP

avg. $1,399 / night

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Castello Di Casole, A Belmond Hotel, Tuscany Design Editorial

Among the oldest inhabited estates in Tuscany, the castello at Casole d'Elsa traces its documented history to the tenth century, when the fortified complex served as a seat of Sienese ecclesiastical power. Castello di Casole, A Belmond Hotel, was carved from that accumulated fabric — medieval watchtowers, a Romanesque chapel, and a later Renaissance villa ranged across a 4,200-acre estate — and converted into a 39-suite property that opened in 2012. The aerial view confirms how little the conversion imposed on the compound: the honey-coloured pietra serena walls and terracotta-tiled rooflines remain exactly as centuries of Tuscan agriculture shaped them, Italian cypress punctuating the forecourt in the manner unchanged since at least the eighteenth century. Inside, the interiors maintain the same discipline of restraint. Bedroom floors are original terracotta cotto laid in herringbone patterns, their warm russet tones grounding baroque-scroll walnut headboards and wrought-iron candle sconces that carry the feeling of a private Sienese palazzo rather than a managed hotel room. Exposed rubble-stone walls in some accommodations push the medieval substrate to the surface. The restaurant unfolds beneath a sequence of brick barrel arches washed in deep burnt sienna, with polychrome encaustic tile floors and cascading Murano glass chandeliers introducing a deliberate note of theatricality. From the infinity pool, the Val d'Elsa rolls away toward Monteriggioni in a view that the estate's original builders understood perfectly well.

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COMO Castello Del Nero

Tuscany, Italy • Chianti • OVER THE TOP

avg. $1,429 / night

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COMO Castello Del Nero Design Editorial

Across a hilltop in the Chianti Classico between Florence and Siena, a twelfth-century castle and its constellation of farm buildings have been drawn into one of Tuscany's most carefully calibrated conversions. COMO Castello Del Nero — forty-one rooms and suites distributed across the original medieval structures — holds to the ridge with the self-assurance of a building that has already survived eight centuries of Tuscan weather and political upheaval, and sees no reason to announce itself differently now. The interiors manage a particular tension with considerable skill: ancient fabric kept visibly intact, contemporary comfort slipped in without apology. Barrel-vaulted stone cellars, their rough-hewn walls and herringbone terracotta floors left entirely undisturbed, are furnished with cobalt and grey velvet chairs and an oversized convex mirror that presses the medieval space into a conversation with something more knowing. Guest rooms sit beneath whitewashed timber beam ceilings or Tuscan plaster vaults, terracotta tile running continuously underfoot, while the furniture — upholstered benches, textured headboards in silvered grey linen, slim iron curtain rods — introduces a deliberately cool, almost Milanese restraint against the warmth of the building. Outside, a long lap pool is edged with clipped hedging and terracotta urns, the Chianti hills opening beyond in every direction, cypress punctuating the view precisely where they always have.

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Borgo Pignano

Tuscany, Italy • Volterra • OVER THE TOP

avg. $1,511 / night

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Borgo Pignano Design Editorial

Two distinct structures collide in the exterior of Borgo Pignano — a medieval fortified tower with Guelph merlons and Gothic biforate windows in rough pietra serena, pressing hard against a later Renaissance villa in warm ochre render, its shuttered windows and terracotta-tiled roofline carrying the proportions of early Cinquecento Tuscan domestic architecture. The tension between them is the estate's whole story: centuries of accumulation on a hilltop above Volterra, converted into a thirty-room retreat set within five hundred acres of organic farmland, gardens, and woodland that the property cultivates as working agricultural land rather than decorative backdrop. Inside, the approach is one of careful restraint — frescoed cornices in soft blue and cream survive intact in the bedrooms, their delicate floral borders left unrestored to preserve the patina of age rather than simulate freshness. Terracotta floors, walnut cassettone chests, iron canopy beds draped in unlined white linen, and checked armchairs in muted wool give the rooms the settled atmosphere of a family house that has been quietly edited rather than designed from scratch. The restaurant, housed in a barrel-vaulted room with climbing-vine frescoes extending across the ceiling plaster, brings Mario Cipriani saddle-leather chairs to tables set beneath a brass chandelier, a large arched window framing the garden beyond. The pool is cut into the ancient stone retaining walls below the villa, its terrace opening directly onto a panorama of the Val di Cecina rolling south toward the coast.

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Borgo Santo Pietro

Tuscany, Italy • Palazzetto • OVER THE TOP

avg. $1,631 / night

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LHW Leaders Club property

Borgo Santo Pietro Design Editorial

Strung across a hillside in the Val d'Orcia near Chiusdino, a thirteenth-century hamlet of stone farmhouses, olive groves, and cypress-lined drives was quietly transformed into one of Tuscany's most romantic retreats by Jeanette and Claus Thottrup, who acquired the estate in 2005 and spent years restoring it by hand. Borgo Santo Pietro now spreads across some fifty hectares of working land — vineyards, kitchen gardens, beehives — with the main villa, a neoclassical palazzetto built around 1800, anchoring a constellation of converted agricultural buildings whose terracotta-tiled roofs are visible from above as warm interruptions in the surrounding green. The interiors carry the feeling of a privately assembled Italian country house rather than a designed hotel, each room furnished differently with antique four-poster beds in carved walnut, crystal chandeliers suspended from exposed timber trusses, gilded Baroque headboards set against hand-painted botanical murals, and aged stone fireplaces framed by lace curtains in cream and ivory. Distressed plaster walls finished in chalky Tuscan tones run through the suites, grounded by worn travertine floors and patterned rugs. The restaurant, with its wide plank floors, rusted steel-framed windows opening onto rolling countryside, and hanging ironwork chandelier, achieves a particular atmosphere — sophisticated without formality. Outside, a curved natural stone pool terrace edged in terracotta amphorae and flowering Mediterranean planting completes the picture of an estate that has always looked exactly like this, even though it hasn't.

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Reschio

Tuscany, Italy • Umbria • OVER THE TOP

avg. $1,699 / night

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Reschio Design Editorial

A medieval fortress rising from the wooded hills of Umbria's Niccone Valley, its rubble-stone walls and watchtower intact after nearly a thousand years, became the unlikely canvas for one of Italy's most quietly obsessive restoration projects. Hotel Castello di Reschio took shape over two decades under the direction of Count Benedikt Bolza, who trained as an architect and treated the eleventh-century castello not as a ruin to be sanitized but as a living document to be read carefully and extended with equal care. The aerial images reveal the full complexity of the compound — terracotta rooflines stepping down the hillside, a medieval tower crowned with a contemporary glass pavilion, cypresses and umbrella pines threading between the structures in arrangements that feel entirely uncontrived. Inside, the thirty-six rooms carry the atmosphere of a cultured private house assembled across generations rather than conceived in a single decorating pass. Exposed chestnut beams, antique terracotta floors, and lime-plastered walls in warm grey and ochre provide the architectural ground; against these, the furnishings layer iron four-poster beds lacquered in deep red, cast-iron clawfoot baths positioned beside arched alcoves, and an eclectic mix of vintage Italian mid-century chairs alongside worn leather club seating. The outdoor pool — a perfect dark ellipse set into a lawn framed by stone pines — mirrors the castello at dusk with the stillness of a Flemish painting. The terrace restaurant extends the same logic outward, copper-shaded table lamps and green rattan chairs arranged against ancient parapet walls, the folded Umbrian hills dissolving into late light beyond.

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Rosewood Castiglion del Bosco

Tuscany, Italy • Val d'Orcia • OVER THE TOP

avg. $2,339 / night

Includes $123 / night in cash back

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Rosewood Castiglion del Bosco Design Editorial

One of the oldest continuously farmed estates in the Val d'Orcia, the medieval borgo at the heart of Castiglion del Bosco dates to the twelfth century, its stone towers and honey-coloured farmhouses arranged across a hilltop in the manner of a self-contained village rather than a single grand house. Rosewood Castiglion del Bosco, which opened in 2012 after an extensive restoration led by the Ferragamo family, preserves that settlement logic — 39 suites distributed across the original borgo buildings, so that guests move between cypress allées and kitchen gardens rather than along hotel corridors. The interiors carry a confident aristocratic ease. Rooms in the main villa show coffered ceilings in pale painted timber, herringbone parquet floors, and curtains in pooled silk falling from iron rods — a layering of textures that suggests an inherited house furnished over generations rather than a decorator's brief executed in one pass. Striped fabric headboards in muted gold and taupe anchor the larger suites, with upholstered chaises positioned toward the French doors that open onto stone terraces with views across the Orcia valley. The restaurant terrace, shaded by a retractable burgundy canopy, frames Montalcino on the opposite hillside as a kind of living backdrop to dinner. Below the borgo, a travertine-edged infinity pool cut into the terraced hillside dissolves into the olive groves and rolling wheat fields that have defined this landscape since the Sienese Renaissance.

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Castello di Vicarello

Tuscany, Italy • Maremma • OVER THE TOP

avg. $2,640 / night

Includes $139 / night in cash back

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Castello di Vicarello Design Editorial

Perched on a hilltop in the Maremma, that wilder, less-visited corner of Tuscany where the landscape rolls toward the Tyrrhenian coast in waves of oak forest and vineyard, a medieval castle that had stood largely untouched for centuries became, under the stewardship of Carlo and Aurora Baccheschi Berti, one of Italy's most quietly compelling small hotels. Castello di Vicarello was not converted so much as tenderly inhabited — the couple spent years restoring the twelfth-century structure by hand, sourcing antiques, salvaged stone floors, and worn kilims rather than commissioning a design studio to impose a coherent vision from outside. The results are visible in every corner: rough-hewn pietra serena walls left exposed in the ground-floor rooms, Moroccan Beni Ourain rugs laid over ancient terracotta, four-poster beds with painted wood frames set against unplastered stone, leather wing chairs clustered around ceramic-based lamps with raffia shades. Upstairs, where the walls are lime-washed to a pale blue-white, parquet flooring in a small-block chevron pattern and carved walnut window surrounds carry a more refined register, plaster busts and framed topographical prints arranged with the ease of a well-loved private house. The infinity pool, lined in deep green marble with a geometric basketweave pattern, draws the eye across a valley of olive groves toward Monte Amiata. Eight suites in total mean the scale never tips into the institutional — the castello functions, at all times, like a home that happens to welcome guests.

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Villa Sassolini

Tuscany, Italy • Arezzo • OPTIMIZE

avg. $198 / night

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Villa Sassolini Design Editorial

Perched above the Val di Chiana on the edge of the medieval hilltop village of Montecarlo Aretino, a centuries-old Tuscan palazzo was converted into Villa Sassolini with a design sensibility that resists both rustic nostalgia and corporate minimalism. The formal garden visible from the property — box-hedged parterres planted with white roses, tall cypresses, and improbable Canary palms — establishes that productive tension immediately: southern exuberance grafted onto a structure of distinctly Umbro-Tuscan austerity, its lime-washed walls carrying centuries of weathering as a decorative finish rather than a flaw to be corrected. Inside, the interiors navigate the same negotiation with considerable skill. Bedrooms are furnished around slender steel four-poster frames — closer to contemporary Italian craft than period reproduction — set against walls in warm venetian plaster tones of ochre, taupe, and amber. Bleached oak floorboards and exposed timber beam ceilings in the upper rooms ground the palette without tipping into farmhouse pastiche, while the restaurant uses oversized wicker-shade pendants and generous slip-covered dining chairs to achieve a softness that flatters the imperfect plaster walls behind them. The pool terrace, cantilevered against the hillside with bronze-canopied parasols and a view across the Chiana valley that reaches toward Cortona, is where the property makes its clearest argument: that a small Tuscan hotel of perhaps fifteen rooms can carry more atmosphere per square metre than properties ten times its size.

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Grand Universe Lucca, Autograph Collection - Image 1

Grand Universe Lucca, Autograph Collection - Image 2

Grand Universe Lucca, Autograph Collection - Image 3

Grand Universe Lucca, Autograph Collection

Tuscany, Italy • Lucca • OPTIMIZE

avg. $249 / night

Includes $13 / night in cash back

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Marriott Bonvoy® property

Grand Universe Lucca, Autograph Collection Design Editorial

Facing Lucca's Piazza Napoleone — the grand civic stage that Napoleon's sister Elisa Baciocchi remodelled in the early nineteenth century — a neoclassical palazzo with ochre-washed render and deep green shutters has been converted into Grand Universe Lucca, part of Marriott's Autograph Collection. The building's four-storey facade, articulated with rusticated stone at street level and arched fanlight windows above, holds its formal composure against one of Tuscany's most ceremonially proportioned squares, where a merry-go-round still turns beneath the plane trees in winter. The interiors navigate the palazzo's bones — vaulted plaster ceilings, exposed timber beams in the upper rooms — with a contemporary palette that avoids the usual period-costume approach to Italian historic conversions. The bar and restaurant spaces preserve their original groin vaults, washed in warm limewash plaster and animated by clustered globe pendants and a sculptural starburst chandelier that hangs low over the dining room's terrazzo floor. Velvet seating shifts between deep plum, forest green, and dusty rose across the public areas, the upholstery choices bold enough to register against the muted stone tones without competing with them. Guest rooms layer saffron-yellow velvet headboards and patterned herringbone parquet with blue-grey abstract rugs and damask curtains, while the upper suites reveal their full ceiling height through the exposed beams — a reminder that the building was always meant to impress, long before it became a hotel.

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Fonteverde Lifestyle & Thermal Retreat - Image 1

Fonteverde Lifestyle & Thermal Retreat - Image 2

Fonteverde Lifestyle & Thermal Retreat - Image 3

Fonteverde Lifestyle & Thermal Retreat

Tuscany, Italy • San Casciano dei Bagni • SPLURGE

avg. $313 / night

Includes $16 / night in cash back

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LHW Leaders Club property

Fonteverde Lifestyle & Thermal Retreat Design Editorial

A seventeenth-century Medici villa perched above the thermal springs of San Casciano dei Bagni, in the southernmost fold of Tuscany where the Val d'Orcia gives way to rolling hill country approaching Lazio — this is the architectural foundation from which Fonteverde Lifestyle & Thermal Retreat derives its entire identity. The main palace building, with its creamy rendered facade, regularised window bays, and wrought-iron balcony railings lined with terracotta urns, carries the measured authority of grand ducal architecture; the Latin inscription running beneath the piano nobile cornice confirms its centuries-old commission. The property expanded considerably in its life as a hotel, the main colonnaded wing housing the restaurant terrace where white parasols and topiary balls now fill the courtyard in a composition that remains faithful to the building's formal geometry. Interiors across the property's roughly 78 rooms and suites settle into a considered monochrome register — cream panelled walls with black-edged curtains, upholstered headboards outlined in dark trim, pale ash floors, and darkened stone accent walls carrying a botanical fresco quality in the villa rooms. Antique prints and warm walnut writing desks ground the scheme without tipping into period pastiche. The infinity pool, edged in pale travertine, frames Monte Amiata directly across the valley — a view that no amount of interior refinement could match, and wisely, none attempts to compete with it.

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Castello di Spaltenna

Tuscany, Italy • Gaiole in Chianti • SPLURGE

avg. $323 / night

Includes $17 / night in cash back

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Castello di Spaltenna Design Editorial

Somewhere between Radda and Castelnuovo Berardenga, on a hilltop that has organized the surrounding Chianti Classico landscape since the eleventh century, a Romanesque parish church and its attached monastery were gradually transformed into one of Tuscany's most quietly serious rural hotels. Castello di Spaltenna carries the full weight of that medieval fabric — rough-hewn pietra serena walls, a bell tower still visible against the skyline, and a cortile whose stone paving and wrought-iron lanterns set the terms for every design decision that followed. The conversion preserved the ecclesiastical bones entirely: the cloister courtyard, now laid with white-clothed dining tables at dusk, retains its brick-arched loggia and the slightly uneven grammar of a building that was never designed to be symmetrical. Inside the 38 rooms and suites, the approach favors absorption over intervention. Exposed chestnut ceiling beams and terracotta floors carry the structural logic of the original building; decorative headboards in damask-patterned fabric, antique carved cassettoni, and Persian kilims layer in a register that suggests a well-inherited country house rather than a designed hotel. The four-poster iron beds visible in the images are spare enough not to compete with the brick-arched openings framing the doorways behind them. The infinity pool, terraced into the hillside with travertine surrounds, pulls the eye across vineyards toward the rolling Chianti ridgeline — a view the medieval monks who built this place would have recognized completely.

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La Bandita Townhouse

Tuscany, Italy • Pienza • SPLURGE

avg. $408 / night

Includes $21 / night in cash back

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Marriott Bonvoy® property

La Bandita Townhouse Design Editorial

Pienza was Pius II's dream of a perfect Renaissance city, built to order in the 1460s and barely altered since — which makes it an exacting host for any contemporary intervention. La Bandita Townhouse, set within a three-storey medieval stone palazzo on the town's main corso, was converted by American owners John Voigtmann and Carlo Scamozzi into a ten-room hotel that holds this tension between historical fabric and deliberate modernity with considerable intelligence. The exterior presents exactly as found: warm travertine and pietra serena, brick-arched openings at ground level, terracotta roof tiles unchanged. Inside the building, the conversation shifts register entirely. The rooms place slim powder-coated steel four-poster beds and pale sage joinery with lacquered orange niches directly against exposed rubble-stone walls — a contrast that reads not as provocation but as honesty about the building's two lives. White-painted timber ceiling beams and wide-plank oak floors ground the palette in natural material while vintage tan leather club chairs and precise task lighting keep the atmosphere closer to a well-edited private apartment than a restored historic inn. The restaurant carries a sharper urban energy: deep burgundy ceramic tiles line the open kitchen behind a raw timber counter, industrial orange Tolix-style stools pulled up to the pass. Beyond the arched openings, the courtyard terrace is furnished with teak benches, canvas directors' chairs, and hanging lanterns, herbs spilling from the surrounding stone walls.

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Borgo Scopeto Relais

Tuscany, Italy • Siena • SPLURGE

avg. $413 / night

Includes $22 / night in cash back

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I Prefer property

Borgo Scopeto Relais Design Editorial

Spread across a working Chianti Classico wine estate between Siena and Castelnuovo Berardenga, the cluster of honey-coloured pietra serena farmhouses and a medieval watchtower that form Borgo Scopeto Relais have been agricultural land since at least the fifteenth century. The conversion to a hotel preserved the hamlet's essential character — rough-cut stone walls, terracotta roof tiles weathered to the colour of dried earth, Tuscan cypress sentinels framing the central cortile — while the interior treatment introduced a restrained country-house register without attempting to disguise its hospitality function. The 49 rooms and suites distributed across the borgo's various buildings share herringbone-laid terracotta floors throughout, a grounding material that connects every category of accommodation to the same agricultural past. Colour does the differentiating work: some rooms carry the cobalt blue of the shutters visible on the estate's exterior, with full-length drapes and accent bedding echoing that signal hue against plastered walls trimmed in red; others warm toward saffron and burnt orange, with white-painted exposed beam ceilings arching over sitting areas that face directly onto the vineyard rows below. The outdoor dining terrace, set against the estate's original stone walls with wrought-iron café furniture shaded by large cantilever parasols, and the rectangular pool terrace edged in reclaimed brick and box hedging, both maintain the same deliberate restraint — nothing competes with the Sienese hills dissolving into the distance.

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Viesca Toscana

Tuscany, Italy • Reggello • SPLURGE

avg. $441 / night

Includes $23 / night in cash back

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Viesca Toscana Design Editorial

Scattered across a shallow valley in the Reggello hills southeast of Florence, a cluster of whitewashed Tuscan farmhouses — their terracotta roofs and shuttered arched loggias unchanged in their essential geometry for centuries — was converted into Viesca Toscana, a small relais that holds its agricultural origins close rather than smoothing them away. The main villa and its dependencies are arranged around clipped lawns and cypress allées in the manner of a working fattoria, the pool terrace framed by stone-edged borders planted with terracotta urns, the whole composition sitting against a backdrop of vineyards and Apennine foothills that makes the aerial view feel almost implausibly complete. Inside, the approach is one of careful restoration rather than reinvention. Original terracotta floor tiles run through every room — worn smooth in the corridors, more rustic in the dining room where white-painted cross-back chairs and dusty-rose upholstered tables sit beneath exposed timber beams and limewashed plaster walls. Guest rooms carry the same material logic: barrelled plaster ceilings, arched casement windows opening onto the countryside, headboards in deep rose or woven fabric, silk drape curtains in sage and gold pooling to stone floors. The furniture throughout draws on a restrained provincial Italian idiom — barley-twist occasional tables, brass-armed bedside sconces, upholstered armchairs in pale celadon — keeping the atmosphere closer to a privately inhabited villa than to a formatted hotel product.

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Castel Monastero

Tuscany, Italy • Siena • SPLURGE

avg. $498 / night

Includes $26 / night in cash back

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LHW Leaders Club property

Castel Monastero Design Editorial

A medieval hamlet in the Chianti Senese, its stone tower and cluster of farm buildings dating to the eleventh century, was transformed into Castel Monastero over a multi-year restoration that preserved the settlement's agricultural character while threading in the infrastructure of a forty-room luxury hotel. The conversion retained the original pietra serena masonry and terracotta roof tiles, and the ensemble — main manor, chapel, outbuildings, and terraced grounds — still carries the silhouette of a working podere rather than a destination resort. A contemporary pavilion housing the pool deck and restaurant loggia sits lower on the hillside, its clean concrete columns in deliberate contrast to the rougher stonework above. Inside, the interiors draw on a vocabulary of aged materials layered with restraint: exposed chestnut beam ceilings, terracotta brick floors worn smooth by centuries of use, dark-stained wood headboards set against limewashed plaster walls. Guest rooms mix antique carved writing tables and button-tufted leather Chesterfield sofas with angular Artemide task lamps, the combination avoiding the dressed-up-farmhouse trap that many Tuscan conversions fall into. The wine cellar restaurant, set within a barrel-vaulted brick undercroft lit almost entirely by candlelight and wrought-iron lanterns, is among the most atmospheric dining rooms in the region — a space where the architecture does most of the work and the decoration wisely steps aside.

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Pieve Aldina

Tuscany, Italy • Radda in Chianti • SPLURGE

avg. $502 / night

Includes $26 / night in cash back

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Pieve Aldina Design Editorial

Ringed by autumn vineyards and silver-green olive groves on a hillside above Radda in Chianti, a twelfth-century Romanesque pieve — a rural parish church with a campanile and adjoining farmstead — was converted into Pieve Aldina, one of the quieter and more considered small hotels in the Chianti Classico zone. The aerial view confirms what the landscape around Radda promises: this is agricultural Tuscany largely undisturbed, the stone complex sitting within its own walled estate as it has for centuries, cypress sentinels marking the boundary between tended garden and open countryside. The interiors navigate the conversion with genuine restraint. Bedrooms retain their original arched plasterwork and terracotta brick floors laid in a herringbone pattern, while the design intervention keeps its voice low — walls washed in sage green and warm white, linen curtains pooling at arched windows, Calder-style wire mobiles suspended from beamed ceilings in a gesture that reads as playful rather than decorative. The restaurant holds its own register: a long upholstered banquette in ribbed oatmeal linen runs the length of a high whitewashed wall hung with an informal arrangement of antique engravings, bentwood café chairs pulled up to dark-stained timber tables. Outdoors, a stone-edged pool framed by umbrella pines and mature olives completes the picture — a property whose considerable atmosphere derives almost entirely from what has been left alone rather than what has been added.

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Lupaia

Tuscany, Italy • Siena • SPLURGE

avg. $603 / night

Includes $32 / night in cash back

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Lupaia Design Editorial

Perched on a hillside between Montepulciano and Torrita di Siena, a cluster of medieval stone farm buildings that had stood largely untouched for centuries was converted into Lupaia, a ten-room relais that treats its age not as a problem to be solved but as the entire point. The exterior stonework — rough-coursed tufa and brick, terracotta roof tiles, a wrought-iron pergola threaded with climbing vines — was left to carry its centuries of weather and repair, lit at dusk with ground-level uplights that turn the facade the color of warm embers. The pool terrace, edged in pale travertine, sits at the property's edge where the land drops away into rolling pasture and cypress-lined ridgelines, the geometry of the water the only thing about the composition that feels deliberately designed. Inside, each room arrives at a slightly different character while sharing the same vocabulary: whitewashed timber beam ceilings, antique gilt mirrors, floors alternating between aged terracotta tile and bleached wide-plank oak. One room pairs a tartan-upholstered headboard with blue-lacquered bedside lamps and a partially open bathroom dressed in navy-and-white chequerboard tile; another layers floral cushions and striped linen curtains beneath vaulted plaster ceilings. The restaurant, framed by a full brick arch and gathered around a massive stone fireplace with a rough-hewn timber lintel, hangs oil portraits alongside gilded mirrors and sets its tables on worn oak boards over a crimson rug — the atmosphere closer to a Sienese family home than a country hotel.

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Toscana Resort Castelfalfi

Tuscany, Italy • Castelfalfi • OVER THE TOP

avg. $1,283 / night

Includes $68 / night in cash back

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I Prefer property

Toscana Resort Castelfalfi Design Editorial

Perched on a hilltop in the Tuscan municipality of Montaione, a medieval village and its surrounding agricultural estate form the physical backbone of Toscana Resort Castelfalfi — a property that TUI Group spent over a decade and hundreds of millions of euros restoring from near-ruin into a working resort of around 120 rooms and suites spread across a borgo that dates to the eleventh century. The aerial view confirms the scale of the intervention: terracotta-roofed wings extend from the historic core in a configuration that respects the settlement's original grain, while a contemporary spa pavilion with a dark cantilevered roof sits tucked into the hillside below. The infinity pool, framed by Italian stone pines and plumbago in full flower, opens onto a Val d'Elsa panorama of folded wheat-and-cypress landscape that no amount of deliberate composition could improve. Inside, two distinct registers operate across the property. The main hotel building carries a polished, urban confidence — warm oak floors, cognac leather bench ends, brass drum pendants, and large-format landscape panels above the beds that echo the view outside in an almost painterly key. The bar works a darker palette of forest-green velvet tub chairs, an onyx-fronted counter, and brass bottle display, closer in mood to a Milanese private club than an agrarian retreat. The casale accommodations take the opposite approach: limewashed beam ceilings, rattan headboards, raw plaster walls, and sienna wool throws that wear the landscape's own colours without affectation.

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Castello Banfi - Il Borgo

Tuscany, Italy • Siena • OVER THE TOP

avg. $1,397 / night

Includes $74 / night in cash back

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Castello Banfi - Il Borgo Design Editorial

Perched on a hilltop above the Brunello vineyards of Montalcino, the medieval fortress that houses Castello Banfi Il Borgo traces its origins to the eleventh century, when the Marchesi Marini built the original fortification overlooking what is now some of the most coveted agricultural land in Italy. The Mariani family — American wine importers who acquired the surrounding Banfi estate in 1978 and transformed it into one of Tuscany's great wine operations — converted the castle and its borgo into a small, deliberately unhurried hotel of fourteen rooms and suites. The castellated watchtower, stone ramparts, and terracotta-roofed outbuildings visible in the aerial view have been left architecturally intact, the conversion working within the existing fabric rather than imposing any contemporary gesture upon it. Inside, the interiors carry the atmosphere of a well-appointed private residence rather than a managed hospitality product. Rooms are dressed in herringbone terracotta floors, exposed chestnut beam ceilings, canopied beds with floral toile hangings in duck-egg blue or raspberry plaid, and case pieces in warm walnut and fruitwood that suggest careful accumulation rather than specification. The restaurant, lined with hand-painted grapevine murals framed in gilded trellis, opens through an arched doorway to a terrace above the valley. The pool terrace below, edged in travertine and flanked by Italian cypresses, frames a panorama across the Val d'Orcia that makes the surrounding Brunello vines feel less like scenery than context.

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Grand Hotel Continental Siena - Starhotels Collezione - Image 1

Grand Hotel Continental Siena - Starhotels Collezione - Image 2

Grand Hotel Continental Siena - Starhotels Collezione - Image 3

Grand Hotel Continental Siena - Starhotels Collezione

Tuscany, Italy • Siena • SPLURGE

avg. $286 / night

Includes $15 / night in cash back

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LHW Leaders Club property

Grand Hotel Continental Siena - Starhotels Collezione Design Editorial

Directly on the Banchi di Sotto, one of Siena's principal medieval thoroughfares and mere steps from the Piazza del Campo, a seventeenth-century palazzo that once belonged to the noble Gori Pannilini family carries the Grand Hotel Continental Siena as naturally as it carries its own stone. The building was converted by the Sienese Chigi Saracini banking family in the early twentieth century and has operated under Starhotels Collezione since 2002, its 51 rooms distributed across four floors of a structure whose street facade — rusticated pietra serena columns framing a barrel-vaulted entrance loggia, an iron lantern suspended above the threshold — has changed little since the palazzo's construction. Inside, the palazzo asserts itself at every turn. Frescoed ceilings with Greek key borders and trompe l'oeil architectural panels establish the decorative register of the grander suites, where canopied beds in gold-and-ivory damask and Venetian carved-glass mirrors sit alongside walnut commodes and powder-blue upholstered armchairs in a way that feels accumulated rather than assembled. The bar occupies a double-height former chapel or ceremonial hall, its most arresting element a monumental antique clock face mounted above the counter, its Roman numerals picked out in gilt against a patinated dark ground. The dining room wraps its terracotta-tiled floors and stucco arabesque ceilings in venetian-red plasterwork hung with Palio equestrian prints, a palette that makes no apology for its Sienese allegiances.