O&C

Laid-Back Luxury in the Heart of Tuscany

Venue: Rosewood Castiglion del Bosco | Location: Montalcino, Tuscany

Set amid the rolling hills of Montalcino, O&C’s September wedding at Rosewood Castiglion del Bosco was an intentional masterclass in laid-back luxury. Welcoming their closest family and friends from the United States for an immersive three-day celebration, the couple curated an experience where timeless Italian landscapes met effortless, high-end hospitality.

Anchored in an organic, earthy color palette, the three-day itinerary leaned into the relaxed beauty of the Tuscan countryside. Day 1 opened with a Welcome Dinner in the Vineyards.

The weekend opened among the estate’s world-renowned Sangiovese vines, setting a warm, celebratory tone with local Brunello di Montalcino, rustic long-table dining illuminated exclusively by candlelight, and golden-hour views. An accordion player filled the evening air with classic Italian popular songs, immersing guests in a timeless atmosphere from the very first night.

Silhouetted guests raising wine glasses in a toast above glowing candles along an outdoor dinner table at sunset at Rosewood Castiglion del Bosco.
Panoramic view of the sun-drenched vineyards and rolling Tuscan hills surrounding Rosewood Castiglion del Bosco in Montalcino, framed by soft foreground grapevine leaves.
Bride and groom holding hands while walking down a gravel pathway lined with cypress trees and a rustic stone farmhouse during golden hour at Rosewood Castiglion del Bosco.
Three traditional Italian folk musicians in fedora hats, waistcoats, and ties playing accordion, violin, and acoustic guitar outdoors by the vineyard at dusk.
Long wooden banquet table lit exclusively with glowing pillar candles for a vineyard welcome dinner at dusk overlooking the Tuscan hills at Rosewood Castiglion del Bosco.

On day 2, we organized a Black-Tie Wedding Ceremony & Reception.

Balancing an easygoing ambiance with elevated elegance, the ceremony took place along the historic fortress wall, flanked by textured white floral runners and endless horizons across the Val d’Orcia. Guests gathered in chic black-tie attire, bringing crisp formal contrast to the wild, sun-drenched landscape.

Bride in a flowing veil and off-the-shoulder gown reading vows into a microphone to the groom in a cream tuxedo jacket overlooking the Tuscan hills at Rosewood Castiglion del Bosco.
Black and white photograph of the bride and groom sharing their first kiss at the end of the aisle framed by white flowers overlooking the Tuscan hills at Rosewood Castiglion del Bosco.
Historic stone chapel facade with arched wooden doors decorated with lush white roses, greenery, and an easel welcome sign at Rosewood Castiglion del Bosco.
Ground-level wedding ceremony aisle flowers featuring white roses, baby's breath, and greenery bordering wrought-iron chairs with wooden seats on a grass lawn.

As dusk fell over Rosewood Castiglion del Bosco, the celebration transitioned into an open-air reception where classic Italian romance met elevated, modern grandeur. Cocktails began poolside, where geometric lanterns and votive candles ringed the water’s edge, mirroring the warm illumination of the historic stone villa in the twilight. Inside an elegant sailcloth marquee, crystal chandeliers dripped from greenery-swathed ceilings above round tables dressed in soft linens, French-style medallion chairs, and tapering candles. Every place setting reflected the day’s bespoke elegance, illustrated personalized menus featuring the couple's custom crest rested on antique floral-patterned porcelain, crowned with a delicate pale rose. The unforgettable evening culminated under the Tuscan night sky with a private fireworks show, illuminating the surrounding cypress trees as O&C stood embraced.

Guests mingling in black-tie attire during evening cocktail hour beside an illuminated swimming pool lined with glowing lanterns at Rosewood Castiglion del Bosco.
Lawn pathway lined with glowing glass lanterns leading to a warmly lit reception marquee tent beside a stone villa at night at Rosewood Castiglion del Bosco.
Elegantly styled outdoor wedding reception marquee at dusk featuring glowing crystal chandeliers, greenery-wrapped poles, round dining tables, and Louis XVI-style chairs at Rosewood Castiglion del Bosco.
Dramatic draped white marquee entrance framed by lush white rose and greenery floral pillars, revealing crystal chandeliers and round dining tables at Rosewood Castiglion del Bosco.
Exterior view at twilight of a grand white sailcloth marquee tent with draped fabric, glowing chandeliers, and floral arches set against an illuminated stone villa at Rosewood Castiglion del Bosco.

Day 3: Poolside Recovery & Open-Air Cinema.

To bring the weekend to a gentle close, guests spent an effortless final day lounging poolside under the warm Tuscan sun, before coming together at dusk for fresh wood-fired pizza, gelato, and an open-air movie screening under the stars.

Outdoor open-air movie screening lounge on a lawn featuring wooden deck chairs with camel-colored blankets, red velvet rope stanchions, and a brick oven decorated with flowers at Rosewood Castiglion del Bosco
Wide shot of an outdoor movie night setup on the lawn in front of a stone villa, featuring a large projector screen, deck chairs, patio heaters, popcorn, and gelato carts at dusk at Rosewood Castiglion del Bosco.
A chef sliding fresh pizza into a glowing brick wood-fired oven outdoors alongside pizza prep ingredients at Rosewood Castiglion del Bosco.
Traditional vintage Italian gelato cart with a striped canopy lit at dusk on a lawn during a wedding evening event at Rosewood Castiglion del Bosco.

Wedding planning: Your Secret Tuscany

Wedding design: Federica Bartolomei

Wedding venue: Rosewood Castiglion del Bosco

Floral design: Flower Living

Photo: Via Imagery

Video: White Arch

Lights: Kaleydo

Noleggio: Preludio Noleggio

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B&C - A winter wedding in Tuscany