Rolling vineyards, sun-drenched hills, and medieval towns—Tuscany’s Chianti region is a dreamscape for travellers who crave more than just a beautiful view. Here, food and wine are not only central to the culture, but to the rhythm of everyday life. For Travel Club members planning their next escape, Chianti offers a delicious way to slow down, savour the moment, and immerse yourself in the flavours of the Italian countryside. From rustic osterias and organic farm estates to architectural marvels blending wine and art, these eight destinations serve up unforgettable culinary experiences—all waiting to be discovered on your next Tuscan adventure.
This elegant osteria blends refined Tuscan cuisine with centuries of winemaking tradition. Surrounded by vineyards and olive groves, it’s the perfect place to unwind with a view of Siena and a glass of estate wine.
Specializes in wild game, fresh pasta, and house-made desserts
Wines from the historic Castello di Fonterutoli estate
Terrace dining with panoramic countryside views
A beloved local favourite, this rustic eatery is all about authentic, home-style Tuscan cooking. Its relaxed garden setting and wallet-friendly wine list make it ideal for a slow lunch or cozy dinner.
Known for gnudi, pici all’aglione, and peposo beef stew
Seasonal menu featuring regional ingredients
Recommended for authenticity and value
At this high-altitude estate, world-class wine meets contemporary art in a one-of-a-kind sensory experience. Intimate tastings are paired with strolls through sculpture-dotted vineyards and ancient cellars.
Signature wines include L’Apparita Merlot and Chianti Classico Gran Selezione
Estate-wide art installations from international artists
Boutique, family-owned experience
This no-frills tavern offers traditional Tuscan comfort food in a rustic cellar brimming with charm. It’s a favorite among locals for hearty dishes and generous pours of Chianti by the glass.
Highlights include truffle ravioli, rabbit stew, and ribollita
Wine shop and tasting cellar on site
Known for casual ambiance and excellent local wine selection
Set in a former Benedictine abbey, this historic estate blends organic farming, refined cuisine, and immersive culinary experiences. Visitors can cook, taste, and stay amid ancient walls and cypress trees.
Offers cooking classes and wine tastings in historic cellars
Dishes made from estate-grown produce and heritage grains
Known for organic Chianti Classico Riserva and Vin Santo
This futuristic, hillside-integrated winery offers an unforgettable journey through Tuscan wine, art, and architecture. At its rooftop restaurant, traditional flavors are reimagined with elegance.
Signature wines include Tignanello and Solaia
Guided tours through state-of-the-art underground cellars
Panoramic tastings and fine dining at Rinuccio 1180
A fortified medieval village turned winery, Volpaia delivers both character and craftsmanship. With estate wines, traditional fare, and historic cellars, it’s a must-stop for wine lovers and history buffs.
Features Chianti Classico Riserva and Super Tuscan Balifico
Tours reveal village-wide winemaking infrastructure
Osteria offers local dishes like tagliata and pappa al pomodoro
Nestled in forested hills, this scenic estate offers a peaceful, old-world wine tasting experience. Its intimate charm and deeply rooted family history make it a true Chianti treasure.
Specializes in Chianti Classico Riserva and Super Tuscan Il Picchio
Guided tastings with light local fare
Explore castle grounds and olive oil production
Chianti isn’t just a destination—it’s an experience that lingers long after the last sip of wine or final bite of handmade pasta. For the curious traveller and passionate foodie, these eight spots offer a true taste of Tuscany’s soul. So pack your appetite and raise your glass. The hills of Chianti are calling, and your next unforgettable food and wine journey starts here: get in touch with Eduardo or India below to begin planning.
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