Castello di Casole, Rosewood Castiglion del Bosco / Bottega53
Tuscany, the jewel of Italy, is an unrivaled canvas for weddings and milestone events. From ancient castles to elegant villas perched on hilltops, every venue here whispers romance, offering endless backdrops for stolen glances, laughter, and promises made under golden skies. Here, we’ve handpicked Tuscany's most enchanting locations where your wedding dreams will come alive, framed by nature’s finest artistry.
Villa Cozzano, Villa San Michele
Il Borgo di Vignamaggio
Tucked between Florence and Siena, Il Borgo di Vignamaggio feels more like a Renaissance painting come to life than a wedding venue. This historic estate unfolds across rolling hills and cypress-lined paths, offering a world of its own for those seeking a celebration steeped in elegance and authenticity. From an intimate chapel with centuries-old frescoes to open-air spaces like La Pergola and La Piazza, every corner tells a story — whether it's a candlelit dinner under the stars or shared vows in the glass-walled Greenhouse. Classic yet surprising, grand yet grounded in nature, this is Tuscany at its most poetic.
Il Borgo di Vignamaggio
Photography: Daniele & Marilia Pierangeli, Amanda Drost
Castello di Vicarello
Romantic and resolutely private, Castello di Vicarello is a 12th-century castle turned luxurious hideaway, set deep in the untouched hills of southern Tuscany. Lovingly restored with an artist’s eye and a collector’s touch, the estate balances medieval charm with quiet opulence — think antique stone walls softened by lush gardens and panoramic terraces that stretch toward the sea. With its mesmerizing gardens and enchanting atmosphere, Castello di Vicarello offers a sense of seclusion that’s utterly transportive. Here, the castle is yours — every key, every view, every hidden corner.
Castello di Vicarello
Photography: Paola Colleoni, Valeria
Borgo Santo Pietro
Borgo Santo Pietro is where old-world elegance meets modern indulgence. Beyond its enchanting gardens and storybook courtyards, you’ll find 20 exquisitely appointed rooms with heirloom details, holistic spa and Michelin-starred dining. At Borgo Santo Pietro, ceremonies unfold in romantic gardens laced with fountains, while open-air receptions glow under the Tuscan sky. For couples who seek elegance with soul, the venue offers both grandeur and grace — and a team ready to make the impossible feel effortless.
Villa San Michele
Reopening its doors in early 2026, Villa San Michele is a Renaissance-era jewel reimagined for modern romance. Originally a monastery, its storied façade, sculpted by the school of Michelangelo, and terraced gardens echo centuries of art and innovation. Today, the villa is a dream setting for weddings with a view. Say your vows in the rose-filled gardens, beside the panoramic pool, or within a candlelit 15th-century hall adorned with frescoes. For a celebration on a grander scale, the entire hotel can be reserved exclusively!
Villa San Michele
Photography: Riley Harper, Carssun
Villa Cozzano
Since 1543, Villa Cozzano has quietly witnessed countless love stories unfold. Nestled in a serene Tuscan enclave, this historic estate marries old-world charm with modern living. Boasting six spacious apartments, Villa Cozzano offers a cozy sanctuary for couples and guests alike. Outside, intimate garden dining spots and a barbecue area invite al fresco celebrations framed by lush nature.
Castello di Casole
Few places capture the spirit of a Tuscan fairytale quite like Castello di Casole. This storied 10th-century estate sets the scene for everything from opulent weddings to intimate elopements and joyful gatherings with family and friends. The options for celebration are as varied as they are magical: candlelit vows in a restored, historic Chiesa S. Tommaso Church, sunset aperitivos on panoramic terraces, or a ceremony beneath the stars in the open-air Amphitheater.
Agriturismo Belagaggio
Agriturismo Belagaggio is a secret garden waiting to cradle your celebration. Surrounded by fragrant herbs and rolling hills, this venue effortlessly blends rustic charm with warm hospitality. Whether you gather inside the cozy farmhouses or by the shimmering pool, every space pulses with the honest beauty of the Italian countryside — a natural canvas for weddings that celebrate life, love, and la dolce vita.
Agriturismo Belagaggio
Photography: Sarbo Studio, Annika Duermeier
Casa Newton
Casa Newton blends the softness of nature with the polish of a private estate. Available as an exclusive, full-service home, it offers the freedom to host your wedding your way—surrounded by those you love, embraced by landscape, and steeped in soul. Casa Newton is perfect for discerning couples who want intimacy without compromise.
Casa Newton
Photography: Fabio Napolitano, Moggi Studio
Rosewood Castiglion del Bosco
Beneath Montalcino’s endless skies, Rosewood Castiglion del Bosco is a living tapestry of natural beauty, Italian heritage, and centuries-old soul. This extraordinary estate offers a curated mix of wedding settings, from a medieval church to a sculptural glass greenhouse and ancient castle ruins. Every corner here invites couples to write their own chapter in a story woven through time.
Rosewood Castiglion del Bosco
Photography: David Bastianoni
Villa Pienza
Understated, intimate, and effortlessly Tuscan, Villa Pienza is made for couples who favor comfort, calm, and authenticity over grandeur. This Val d’Orcia country house invites you to slow down and savor the simple joys of an intimate celebration. Inside, cozy lounges and spacious bedrooms with super king-size beds offer a serene retreat, while the Tuscan-style kitchen combines rustic charm with modern convenience. Outside, aromatic herb gardens and wildflowers frame the shimmering pool, and a spacious portico with a long dining table sets the stage for relaxed al fresco feasts.
Villa Pienza
Photography: Eros D’Angelo, Sebastiano Colaluce
Reschio
Hidden deep in the rolling Umbrian hills, Castello di Reschio is a thousand-year-old fortress reborn. Meticulously restored, this historic castle now offers contemporary comfort wrapped in timeless stone walls. Exchange vows in the intimate chapel dedicated to the Virgin Mary or just steps away in the enchanting Church of San Michele Arcangelo. From elegant dinners at Alle Scuderie to lively evenings in the Garden Courtyard or moments of quiet reflection in the Palm Court, every corner of Reschio invites you to craft unforgettable memories steeped in history and beauty.
Villa Cora
Villa Cora brings a fresh energy to the Tuscan wedding scene. Set just outside Florence’s historic center, this 19th-century mansion balances classic architecture with eclectic interiors and vibrant personality. Think mirrored walls, frescoes, chandeliers, and a poolside garden made for golden hour champagne toasts. An unforgettable setting for couples who want tradition with a twist.
Villa Cetinale
In the peaceful Ancaiano hills, Villa Cetinale stands as a stunning testament to Roman Baroque grandeur, built in 1680 by Cardinal Flavio Chigi. Inside, antique elegance meets modern ease, creating a timeless and inviting atmosphere. Yet, it’s the villa’s renowned gardens that truly steal the spotlight — celebrated as some of Italy’s most exquisite. These lush, sculpted grounds offer secluded alcoves ideal for symbolic ceremonies, effortlessly accommodating weddings both intimate and grand in scale.
Monteverdi
In Castiglioncello del Trinoro, a village barely touched by time, Monteverdi redefines Tuscan hospitality with quiet precision. Every detail is intentional, every space considered. With its restored architecture and understated aesthetic, Monteverdi offers a refined setting for couples who prefer substance over spectacle. Guests are invited to settle into the hotel’s design-led rooms, suites, and private houses — where seclusion meets sophisticated comfort.
Monteverdi
Photography: Kelsea Holder, Suzy Anderson
Villa Scorzi
Villa Scorzi offers a versatile and romantic canvas for designing a celebration that’s entirely your own. From sun-drenched gardens to hidden courtyards, the estate’s outdoor spaces provide a picture-perfect backdrop for every chapter of your day—ceremony, cocktails, or golden-hour portraits. Indoors, expansive, air-conditioned rooms welcome guests in every season, combining comfort with timeless Tuscan charm.
Villa Scorzi
Photography: Linda Nari
