The 8 Best Wine Estate Hotels in Italy

Stay at one of these award-winning Italian wine estates and wake up in a vineyard.

View of Villa Medicea di Lilliano Wine Estate
Credit: © Villa Medicea di Lilliano Wine Estate

Explore hidden Tuscany in Montecucco, the dramatic Prosecco Hills or the salt flats of Sicily by staying at these boutique Italian wine hotels for unforgettable experiences that don’t exist anywhere else. Instead of just tasting the terroir, wine hotels invite you to stay awhile and become a part of it. 

1. Villa Medicea di Lilliano Wine Estate, Tuscany 

In the Chianti Colli Fiorentini hills, a quick hop from Florence, this family-owned magical treasure is perfectly situated to explore Italy’s iconic Chianti wine region. Contemporary and chic, yet rustic, Villa Medicea di Lilliano Wine Estate is a historic luxury bed and breakfast residence. Think terraced gardens, fairy lights, stylish courtyards, vineyard views, and tranquil swimming pools. A coveted wedding venue, the estate is often featured in magazines for its effortless Tuscan charm and five-star events. 

Enjoy relaxed Tuscan sophistication in two residences on the private estate. Centuries-old, the La Torre residence has five sophisticated individual villas that pop with color. In the courtyard, arches bloom while scents of lavender and rosemary linger in the air. The equally luxurious La Corte Villa boasts views of the Duomo. Each villa has a private pool surrounded by lush foliage with views of the Florentine hills, vineyards, and olive groves.

Time well spent here is best counted by empty glasses of Diletta Malenchini’s award-winning organic wines. Lovely blends of Sangiovese, Canaiolo, and Pugnitello grapes delight the palate. Pour yourself a glass and stroll through 70 hectares of organic vineyards and olive groves. Sip by the pool, take a cooking class or book a private dinner and fill your day with magical moments and romantic surprises. 

2. Agrirelais Baglio di Pianetto, Sicily

The family-owned legacy winery hosts guests at the Agrirelais Baglio di Pianetto. In the Santa Christina Gela hills surrounding Palermo, the estate is nestled in-between vineyards and ancient olive tree groves in Sicilia DOC – famously known for Grillo, Frappato, and Nero d’Avola grapes. The epitome of Sicilian hospitality, the elegant and spacious agrirelais offers endless vistas from its infinity pool and balconies to drink in the views as you sip on the estate’s organic and natural wines.

Known for hand-harvested Sicilian wines with an elegant French savoir fair, the Baroni Estate produces fragrant white wine, library reserves, monovarietals, and natural wine from grapes that grow beautifully in the dry rocky Sicilian terroir.

3. Tenuta Le Cave, Valpolicella 

In the Valpolicella valley, between Verona and Lago di Garda, is Tenuta Le Cave. Sustainability marries Italian elegance at this eco-luxury wine hotel that boasts lush views of organic and biodynamic vineyards. Bask in the sun beside its Roman-inspired pool with vineyard vistas. Relax in a Finnish sauna, salt grotto or book a holistic massage at its wellness center. Each of its suites is uniquely decorated with eco-friendly furniture set against ancient stones and rich wood tones in a refined classic Italian style. 

Join the estate’s sommelier for a sophisticated wine experience with six organic Valpolicella DOC wines paired with delectable appetizers. Then stay for a sunny lunch or moonlit dinner at Tentua Le Cave’s epicurean restaurant. Its seasonal menu takes a refined spin on classic Italian dishes that are perfectly paired with Fasoli Gino and Tasi wines made with aromatic Valpolicella, Ripasso, and Amarone grapes.

4. Agriturismo Baglio Donnafranca Wine Resort & Farm Resort, Sicily

Travel to western Sicily, just minutes from Marsala, and you’ll find Agriturismo Baglio Donnafranca Wine Resort. Surrounded by vineyards with sparkling Mediterranean views, select a bottle of reserve red, pour yourself a glass, and watch the glowing red sunset from the pool or panoramic terrace.

On the property is Tenuta Ansaldi where winemaker Giacomo Ansaldi works his magic. Try the Cipponeri Rosso Riserva produced from organically grown indigenous Perricone and Nero D’Avola vines. And his refreshing champagne-method Ansaldi Brut. Sicilian wines are known for their freshness like the Donna Franca Abbadessa Sicilia IGT which has a touch of citrus notes.

Take a ride on one of the hotel’s complimentary bikes and explore the vineyards and the countryside of Marsala. Notable wineries to visit are Cantine Fina with its stunning rooftop perfect for sunset tastings. And Tenuta Gorghi Tondi whose grapes are organically grown in a nature reserve in Trapani. 

5. Relais Cà del Poggio, Treviso 

For unforgettable views of the Hills of Prosecco, a UNESCO world heritage site, book a room at the Relais Cà del Poggio. Midway between Venice and the dramatic peaks of the Dolomites, its patio (and jacuzzi) offer endless vineyard views dotted with charming hilltop towns. First famous for its Restaurant Ca’ del Poggio specializing the freshest seafood from the Adriatic Sea, the hotel became a favorite for contemporary charm and service. The view pairs perfectly with a glass of Cà del Poggio Brut Prosecco Superiore. Known for its elegant perlage and bouquet, this fine wine will delight your palate. 

To discover more producers, book a tour with Visit Prosecco Hills for insider knowledge on the best organic vineyards including Toffoli and L’Antica Quercia. Or visit the historic underground cellar of Villa Sandi with its impressive seventeenth-century Palladian-style estate. 

6. Villa Rignana, Tuscany 

Stretching from Florence to Siena, the world-renowned vineyards of Chianti Classico are said to be the most authentic. Nestled amongst rolling hills is the charming Villa Rignana. Centuries-old, it’s an organic farm producing quality olive oil, wine, and vegetables. Between the woods, vineyards, and olive groves you’ll find the beautifully redecorated Tuscan Villa Rignana. With nine double rooms, you can book the entire villa or individual suites. 

Its restaurant, La Cantinetta, is a historic restored old oil mill with a traditional rustic Tuscan menu and endless views of Chianti. Here is the perfect opportunity to discover their organic fine wines made from Sangiovese, Canaiolo, Merlot and Cabernet Franc.

7. Tenuta di Montecucco, Tuscany 

Wine lovers in the know head to Montecucco, famous for high-quality Sangiovese grapes at a wonderful value. Stay on the historic estate of Tenuta di Montecucco in one of its twelve renovated apartments in a restored village surrounded by vineyards and olive trees. It’s your choice to visit the historic wine cellar dating back to the 1300s or a modern architectural gem, Castello ColleMassari organic winery and wine cellar.

While in Montecucco, explore its La Strada del Vino (wine road) and discover more under-the-radar organic wineries including the talented Innocenti brothers of Peteglia, astrologically-farmed Basile with zero environmental impact, and award-winning Le Maciarine. 

8. Castello Vicchiomaggio, Tuscany 

While wine tasting, why not stay in a castle? Just between Florence and Sienna is Castello Vicchiomaggio, a sustainable and award-winning wine estate in Chianti Classico that spans 140 hectares of vineyards, olive trees, and forest. Sangiovese, the most important grape for Chianti Classico, grows beautifully in its rich clay soil. For an unforgettable experience, stay in one of its renovated suites, swim in the pool overlooking vineyards and forest, and dine outdoors basking in Tuscan countryside views. 

While day-tripping through Chianti Classico a visit to organic Fontodi in the famous Conca d’Oro region is a must. And Monte Bernardi’s biodynamic wines are elegant and delicious and will make even conventional wine drinkers a slow wine convert. 

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