Situated in the Montalcino region of Tuscany, this luxury resort spanning 5 acres sits within an 800 year old estate comprised of ancient castle ruins, a medieval church, a historic village, a world-class vineyard, a private members' golf club and sprawling grounds

What’s the secret sauce at Castiglion del bosco? (And no, it’s not Chef Matteo Temperini’s famous ragù di manzo…. Though you’d be forgiven for thinking so!) It's the all-inclusive nature of this luxury Tuscan retreat (sans mediocrity). Not only can most, if not all, of your wedding guests be accommodated on-site thanks to the 42 spacious suites and 11 luxury farmhouse villas, this 800-year-old hilltop village turned gold standard rendezvous boasts a dynamic array of event spaces with varying levels of formality, styles and views which make for a seamless, multi-faceted weekend of events. The outstanding level of service appeals to even the most demanding clientele, and the handsome aesthetics that marry old world Italian heritage with sophisticated modern comforts make for a well-tailored sanctuary for groups of all sizes. 

Rural chic with olive, corn-gold and russet hues

Luxury farmhouse with modern sophistication + tailor-made style


 360-degree views of UNESCO-protected Val d’Orcia Natural Park

The tiny hilltop town of Montalcino


Ancient Village Turned Luxury Resort, Winery, Spa & Golf Course

Partial Use & Full Buyout Options


A luxury wedding venue in the Tuscan countryside with a holistic approach to wellness + sustainability, spanning 300 acres of gardens, orchards, forests, vineyards and a restored 13th c borgo

Photos by Matteo Carassale + Courtsey of Rosewood Castiglion del Bosco


Culture breeds beauty, and this fixture of Etruscan Tuscany offers infinite allure. The vibe is elegant, polished and refined - both tailor-made interiors and lovingly tended exteriors boasting the level of style + design you'd expect from the Ferragamo family... fitting when you consider it was this very Italian fashion mogul who created the Tuscan Utopia we're talking about today. A harmonious blend of natural earth tones fraternizes with luxurious leather textures from the handsome lounge areas to the cobblestone-studded piazza connecting the stables-turned-guest suites to rustic chic osteria. As for the land? Expect truffle-rich woods, grapevines in rippling succession, a coterie of olive trees, seasonal vegetables in their glorious adolescence, and budding roses opposite beds of lavender and rosemary. What's more, the medieval ruins are preserved in effortless allegiance with the resort's most cutting-edge features - lookin' at you, panoramic pool! If you've ever wanted to feel like Frances in Under the Tuscan Sun, this is your chance.

Photos courtesy of Rosewood Castiglion del Bosco


You've seen the immaculate views. The ones overlooking the expansive and mountainous terroir below. The ones brought to global prominence the moment Kate Upton & Justin Verlander's wedding hit the front pages. Mist-shrouded forests, emerald green vineyards and sloping fields of gold are all visible from this hilltop perch with natural event spaces tiered like layers of a cake.

There's the Garden of the Castle Ruins - a highly coveted spot for Ceremonies at the tippy-top of a winding grand stone staircase. Then there's the intimate 12th-century church, which maintains bragging rights for housing 14th c Lorenzetti frescoes reminiscent of Giotto and the ability to perform a ceremony with a Catholic rite. After making things official, mingling + noshing can be enjoyed in picturesque spaces like the Pool Terrace, Terrazza Quadrata, Belvedere Garden, Kitchen Garden, the Capanna Vineyard and/or the resort's central and signature piazza. For larger guest counts, Rosewood Castiglion del Bosco can pitch the prettiest greenhouse marquee you ever did see - and right next to the medieval castle ruins to boot!

 It goes without saying that the resort is well-equipped to host auxiliary events like pizza parties, vineyard tours, spa days, golf outings, pool parties as well. That's the magic of keeping everything on-site! There are layers upon layers of paradise to be discovered. 


Within the heart of the estate lies the Borgo, hosting 42 suites and 3 of the 11 villas within walking distance of both on-site restaurants, the spa, the kid's club, the gardens and the fitness room. The other 8 villas have established permanent residency amidst the breathtaking Tuscan landscape. Wherever you sleep, the views of the morning mist rising and sweeping across the Val d'Orcia are magical.

Stately, traditional and unequivocally homey, these temporary habitats for up to 172 guests are endearingly comfortable. Souped-up country interiors attract lovers of modern rustic style. There's no shortage of four-poster beds, thick curtains and artfully placed antiques here! Styled by Chiara Ferragamo herself, the rooms burst with character and artisan craft. 

Don't even get us started on the villas - tranquil countryside havens with their own private Edens, kitchens and 3-6 bedrooms each. The Parmigiano on top is the promise of one private pool per villa, each equipped with BBQs and/or wood-fired ovens for low-key pizza nights. Ladies and gentlemen, we have reached the Promised Land. 

Photos courtesy of Rosewood Castiglion del Bosco


If Italian rustic hygge was a thing, the cozy al fresco Osteria Canonica would embody it. On the other hand, the Ristorante Campo del Drago appeals to those of more gourmet persuasions. Bottom line, you can expect atmospheres of genuine serenity from both on-site restaurants and a promise of spirited collaboration for all wedding weekend event menus. Endeavoring to whisk together an approachable, creative yet utterly nostalgic menu, the Chef finds his stride in dishes like hare pappardelle, Tuscan pigeon punctuated by pomegranate glaze and perfectly crisp wood-fired pizzas with fresh veg + cured meat toppings. 

Old-style cooking with seasonal ingredients plucked from the Vatican-landscaper-designed organic kitchen garden on-site can be expected for the food - simple, yet powerful flavors that give Tuscany its Italian comfort food reputation. Of course, Chef Matteo Temperini doesn't discriminate when it comes to superb ingredients. He'll often call upon his trusted network of like-minded locals to supply the top billings for his most innovative and crowd-pleasing dishes. Truffles of the Senese Crete, porcini mushrooms from the Amiata... even his pasta pomodoro is made from 6 different types of locally grown tomatoes. That's amore commitment.

As for the wine, this region is most famous for its Brunello di Montalcino, and the Rosewood is the 5th largest producer of this lush red that's continually praised by seasoned sommeliers and amateur wine enthusiasts alike. The wine list simply exceeds expectations, representing nearly all of the region's 240 producers - a noble effort indeed. One tasting in the winery's 
"barricaia" - an oenological sanctuary where the finest wines age for 6 to 36 months within French oak barrels - and you'll be begging to revisit this hibernation station every single day. From the silky top cuvées to the rich, berry-forward Brunellos to the earthy Sangiovese verticals, it's easy to see why the Rosewood Castiglion del Bosco has become a destination to sip, stay and play.  


Resting on 5,000 picturesque acres within the Val d'Orcia Natural Park, you can't help but feel like you've stumbled into a golden-plained version of C.S. Lewis' Narnia as you enter this verdant reserve. Teeming with life and natural beauty, the resort stretches across the famed Via Francigena, an ancient route historically traversed by merchants and pilgrims. You'll feel secluded, but never stranded, in these rather aristocratic digs that take, more or less, 15 minutes to drive across. The views are enough to make time stand still, as are the offerings of aged Pecorino and Brunello di Montalcino waiting for you upon arrival.

Should you get cabin fever - you won't - Siena is only a 45 min drive from the estate. Buonconvento and Montalcino are each about 15 minutes by car. So if you're itching to embrace your thrill-seeking side and cycle the iconic L'Eroica bike track in Chianti or wind through the hills + woods of the Crete Senesi in fall, far-flung adventures are afoot for those who wish it. 

As for the homebodies and slow-living practicers among us, there are endless ways to engage your senses within the cypress-studded confines of this ancient Italian hamlet. Guided truffle hunting in the Tuscan woodlands, private helicopter rides over the vineyards of the Val d'Orcia, pasta-making classes, bespoke wine tastings + experiences, star-gazing sessions, elegant spa treatments, horse riding, hiking, cycling, or vintage Jeep Defender cruising throughout the expansive and dynamic property... there is enough here to create a lifetime of bliss, much less a weekend! 

Photos courtesy of Rosewood Castiglion del Bosco

"In this pristine estate with timeless charm, guests find that sense of home that we Italians know how to create. Warmth, hospitality and comfort blend with elegance and excellence.” - Chiara Ferragamo


Get married at Rosewood Castiglion del Bosco if you're lovers of culture, food, nature and romance. Luxuries feel harmonious with the land from farmhouse villas to enriching excursions, making it an excellent choice for couples in search of a destination wedding venue where they can house most, if not all, of their guests while offering a vast array of extracurriculars they can enjoy on their own time or as part of a group activity. 

The massive size of the estate also lends itself to partial hires, where you can still enjoy the bounties of the property without the price tag of a full buyout. Even so, your bottom line for the venue rental + food and bev minimum will be on par with the quality of the venue spaces, amenities, services and standards of excellence. As always, brace yourself for some sticker shock, but know that trust is priceless.

Picture this: you set your family, bridal party and other VIPs up in a handful of the villas across the property. Perhaps the two-story Villa Gauggiole for its post among the vines (a surefire winner with the in-laws) or the spacious Villa Agresto for your gal pals. A pre-wedding wellness day by that pool? Yes, please. We also love Villa Alba, with its cozy country kitchen and shaded panoramic terrace. But enough about the rooms! 

The festivities for a multi-day destination wedding at Castiglion del Bosco might kick off with a Welcome Party in the Piazza of the Borgo - red + white checkered tablecloths and wicker-wrapped olive oil bottles in full effect.  

The next day would promise recovery for you and your guests - a chance  to explore the widespread grounds both within and beyond the resort. A group excursion might be on the table if you want your guests to explore the Brunello di Montalcino vineyards - by hot air balloon or on foot. You might organize a short day trip to Siena or 18 holes of golf without traveling far. Or perhaps a fleet of horses (or horsepower) gives your guests a chance to relax and take in the views from the truffle-filled forests of the Val d'Orcia to the terra cotta roofs of Montalcino. 

Day 3 might be the wedding day - a ceremony in front of the medieval castle ruins, followed by cocktails in the kitchen gardens. (What better conversation pieces exist than those crafted by the hands of Vatican landscapers?) The evening would culminate inside the glasshouse marquee - a sophisticated "old school Tuscan" feast succeeded by the greatest party these hills have ever known... and that's saying a lot. They've seen centuries of festeggiamenti.

A casual send-off brunch by the hotel's famous infinity pool is an easy epilogue to the weekend's events, though if it were us, we'd take advantage of the renowned on-site winery and host a cheese + wine picnic in the vines.  

How to Reach Rosewood castiglion del bosco


Florence Airport (FLR) 
1 hr, 30 min

Siena Airport (SAY)
45 min

Grosseto Airport (GRS)
45 min

Those opting for charter helicopter service can make use of the resort’s private helipad.

Address: Località Castiglion del Bosco, 53024 Montalcino (Siena), Italy



Stazione di Buonconvento
15 min 

Services connecting in Siena, Grosseto and Florence


15 min

15 min

45 min

1.5 hrs

Please note that car hire is available at the Florence airport, but not the Siena train station, so be sure to arrange the appropriate transfers with the Rosewood team in preparation for you and your guests. They have wonderful access to luxury cars or vans for larger groups. 

Photos courtesy of Rosewood Castiglion del Bosco

Castello di Vicarello

Villa San Michele

Borgo Santo Pietro

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