
Gaiole In Chianti (SI), Italy
Villa Gaiole
Offering panoramic vistas over Chianti’s rolling hills and woodlands, Villa Gaiole is a serene Tuscan retreat that sleeps up to 14 guests across seven luxurious bedrooms.
From £12,109 per week
Radda in Chianti SI, Tuscany, Italy
Sleeps 105 bedrooms7 bathroomsPrivate pool

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Villa Sienese Del Tramonto is a remarkable 17th - century estate that masterfully blends noble heritage with luxurious modern living, set amidst the rolling vineyards and olive groves of Tuscany’s Chianti region. Meticulously renovated over five years, this 450 - year - old villa once played a significant role in the history of Radda in Chianti - a village renowned for its world - class wines, scenic cycling routes, and vibrant local festivals.
Originally a noble residence and strategic watchtower, the villa still features its ancient architectural centrepiece, offering panoramic sunset views across the Chianti hills. Each of the villa’s beautifully appointed suites is individually styled in blue, pink, green, yellow, or taupe, creating a unique and inviting ambience in every room.
The interiors are a seamless blend of historic charm and state - of - the - art amenities, including terracotta floors, vaulted ceilings, and antique furnishings complemented by a fully integrated Loxone smart home system, sleek indoor switches, and underfloor radiant heating and cooling for year - round comfort.
Outdoors, guests can unwind beside the swimming pool, dine al fresco under the covered veranda, or stroll through manicured gardens. The expansive lawn is ideal for private events or peaceful lounging, with ambient outdoor lighting enhancing the villa’s serene setting.
Just 400m away, the historic village of Radda in Chianti is within easy walking distance, offering cafés, restaurants, and cultural attractions. For added convenience, the property also features a separate service entrance and parking area for staff or additional guests.
Perfectly positioned between Siena, Florence, and San Gimignano, Villa Sienese Del Tramonto offers an unforgettable Tuscan escape.
Nestled above the rolling vineyards of Chianti Classico, Radda in Chianti is a medieval hilltop village between Florence and Siena, offering a picturesque blend of history, wine culture, and tranquil Tuscan charm.
Surrounded by a sea of grapevines, the town is home to centuries‑old stone buildings, narrow cobbled streets, and scenic squares like Piazza Matteotti and Piazza del Podestà, where visitors can admire the historic Chiesa di San Niccolò.
Radda lies at the heart of Tuscan wine country, with numerous nearby wineries offering tastings, cellar tours, and gourmet lunch experiences amidst olive groves and vineyards. Wine festivals like Radda nel Bicchiere bring the village to life in autumn with hundreds of regional vintages served in local piazzas.
Outdoor lovers can enjoy scenic hiking and cycling routes through the Chianti hills, including paths that lead to the charming medieval hamlet of Volpaia, perched above the vineyards. Vespa and e‑bike tours are also popular ways to explore the area’s vistas and artisan wineries.
Despite its small size, Radda offers fine dining and local trattorias, along with cosy wine bars and specialty food shops - perfect for sampling local prosciutto, olive oil, cheeses, and classic Chianti wines. With its timeless atmosphere, world - class wine tours, and unspoiled landscapes, Radda in Chianti offers an authentic and unforgettable Tuscan experience.
Radda in Chianti SI, Tuscany, Italy. Farmhouses and palazzi where dinner is the main event.
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Gaiole In Chianti (SI), Italy
Offering panoramic vistas over Chianti’s rolling hills and woodlands, Villa Gaiole is a serene Tuscan retreat that sleeps up to 14 guests across seven luxurious bedrooms.
From £12,109 per week

Iano di Montaione (FI), Italy
Perched upon a small hill in the endlessly undulating terrain of rural Tuscany, Villa Dei Cedri offers luxury accommodation for 12 guests in this breathtakingly scenic landscape.
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Enveloped by verdant countryside in the beautiful Val d'Orcia and yet within easy access to the historic city of Siena, Villa Gino offers guests the perfect location to explore the many parts of Tusca…
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