Discover Chianti
An immersive journey through the flavours, landscapes, and living traditions of Tuscany's most storied wine region
From private chef dinners beneath ancient stone arches to sunrise yoga overlooking the Chianti hills - every experience at Le Rondini is an invitation to live as Tuscany was meant to be lived.
Four categories · Twenty experiences · One unforgettable stay
Where the Route Passes
Two of Italy's most legendary sporting events trace their path directly past the gates of Le Rondini — the roar of vintage engines on the Mille Miglia, and the silent determination of runners on the Chianti Ultra Trail.
Mille Miglia
The legendary 1,000-mile vintage car race from Brescia to Rome and back — one of the most celebrated motoring events in the world. Each June, hundreds of pre-1957 cars thunder through the Chianti hills on the original route. The road in front of Le Rondini is part of the course. Watch Ferraris, Maseratis, and Alfa Romeos pass from your terrace with a glass of prosecco in hand.
June · The route passes directly in front of the villaChianti Ultra Trail
An ultra-distance trail running event through the vineyards, olive groves, and medieval villages of Chianti Classico. Runners from across Europe trace ancient paths that wind past Le Rondini's gates — the same trails you can walk any morning of your stay.
Spring · Trail passes the villa gates
Private Chef Dinners
As the last light fades, you slip into town for aperitivo or settle on the terrace with a glass. Meanwhile, your in-villa private chef begins cooking. Ingredients come from the villa's garden, or sourced locally. The menu follows the season, the harvest, and the conversation. Dinner unfolds beneath the stars on the terrace, or in La Cantina's candlelit stone arches, where every whisper carries.
- Four course Tuscan menu
- Optional wine pairings on request
- Served on the panoramic terrace or in La Cantina
- Local ingredients
Tuscan Cooking Classes
Learn the art of handmade pici, pappardelle, and traditional sauces using herbs and vegetables from L'Orto, our organic kitchen garden.
Wine Tastings
The enoteca from the village brings the bottles up to the terrace. A guided tasting of whites, Chianti Classico, Riserva, and Brunello, with the Chianti valley as your backdrop.
Cellar Evenings
Restored over a year by two master craftsmen, the seventeenth-century cantina sits beneath the villa. Candlelight, conversation that carries through the arches, and whatever the night calls for: dinner, tasting, music, or simply the company.
Traditional Fire Cooking
The ancient stone barbecue, fire burning down to embers. Bistecca Fiorentina, Cinta Senese pork and sausages, Tuscan lamb, traditional sides, and vegetables from the villa's garden. Vin Santo to close. A traditional Tuscan welcome to the villa.
Sunset Aperitivo
Aperitivo in hand, watch the valley turn colour. Terracotta to gold, olive groves to silver. Dinner follows when the light goes.
Yoga & Wellness
Morning or sunset sessions on the terrace, overlooking the valley - guided by the sound of birdsong and the scent of rosemary.
Long Lunch on the Terrazza
A slow Tuscan lunch overlooking the Chianti hills — three hours of seasonal courses, local wines, and the kind of conversation that only happens when no one is watching the clock.
Winery Visits
Visit the acclaimed cellars of Chianti Classico - Castello di Volpaia, Badia a Coltibuono, Castello di Brolio - and taste vintages unavailable outside Tuscany.
Cheese Producer Visits
Meet artisan cheesemakers crafting pecorino toscano and fresh ricotta using methods unchanged for generations in the hills of Chianti.
Porcini Mushroom Picking
Forage for porcini beneath the chestnut canopy after the autumn rains - then bring your harvest back to the kitchen for a risotto you will never forget.
Olive Oil Tastings
Tour centuries-old olive groves and taste freshly pressed extra virgin oil with a master producer - learning to read colour, aroma, and pungency.
Truffle Hunting
The Lagotto's nose twitches. The dog has caught something in the damp oak forest - the earthy, unmistakable scent of tartufo nero. The trufolao, a hunter who knows these woods like his own garden, kneels and extracts a black diamond from the soil with practiced care. By noon, you have a basket of truffles. By evening, they are shaved over pasta in La Cantina, their perfume filling the stone vault. This is autumn in Chianti. This cannot be replicated.
- Hunt with trained Lagotto Romagnolo dogs
- Search oak forests with an expert trufolao
- Cook your harvest at the villa
- Tartufo nero from Chianti soil
Hiking in the Chianti Hills
You step from the villa gates onto paths that connected medieval villages before roads existed. The Chianti hills roll before you - vineyards striped with autumn colors, olive groves silvery in morning light, cypress trees standing like sentinels along ancient boundaries. Walk to Radda for coffee, hike to Volpaia for lunch, or trace the ridges where Siena's towers puncture the horizon. The air smells of wild fennel and sun-warmed earth. Your legs will ache. Your spirit will soar.
Cycling Through Vineyards
Horse Riding
Vespa Countryside Tours
There is no other way to say it: you are riding a Vespa through Tuscany. The wind carries scents of cypress and warm stone. The two-stroke engine buzzes as you lean into curves between vineyards that have produced wine since before Columbus sailed. You stop in Radda for aperitivo, in Panzano for lunch, in Greve for no reason except the pleasure of arrival. The helmet goes on. The world becomes simple. This is the Italian dream, and it is real.
Florence, Siena & San Gimignano
From Le Rondini, the treasures of Tuscany unfold in every direction. Florence, forty minutes north, holds the Uffizi's Botticellis and Brunelleschi's impossible dome. Siena, thirty minutes south, guards the Piazza del Campo where horses thunder twice each summer. San Gimignano rises from the valley like a medieval Manhattan, its towers the skyscrapers of a forgotten time. We arrange private guides, skip-the-line access, restaurant reservations. You simply arrive.
Historic Castles & Medieval Villages
Explore the fortified hamlets of Chianti Classico - Castellina, Volpaia, Gaiole - where time moves at a different pace and every stone has a story.
Radda in Chianti is a three-minute walk from the villa gates. These are the places we send every guest — the restaurants, wine bars, and cafés that have earned their place through years of quiet excellence.
Restaurants
Pizza Pie
Relaxed pizzeria — the best pizza in town. A local favourite for families and casual evenings.
Casual · PizzaRocchiggiani Fino & Figlio
Excellent steaks and traditional Tuscan meats. A proper butcher-turned-restaurant where the bistecca is taken seriously.
Traditional · Steaks & MeatsLa Loggia del Chianti
Refined regional dishes in an elegant setting. The head chef is also our designated chef for private dining experiences at the villa.
Fine Dining · Our Private ChefRistorante Enoteca di Colle Bereto
Elegant dining with one of the best wine-by-the-glass selections in the area. The terrace has exceptional views.
Fine Dining · Outstanding Wine ListWine Bars & Aperitivo
Casa Porciatti Wine Bar
A historic enoteca with a remarkable selection of Chianti Classico and other Tuscan wines. The kind of place where you learn something with every glass.
Historic Enoteca · Chianti ClassicoLa Bottega di Giovannino
Charming local wine shop and bar, perfect for discovering regional bottles you will not find at home.
Wine Shop & BarBar Dante
Classic Italian piazza bar, ideal for aperitivo or a relaxed meal. They also have a comprehensive wine cellar and stock cigars and whiskies for guests who want a change of pace.
Piazza Bar · Wine Cellar · Cigars & WhiskyBreakfast & Gelato
Sandy
A local favourite for breakfast pastries, curated wines, and the best gelato in town. Start your morning here or end your evening walk with a cone.
Pastries · Gelato · WineWithin Easy Reach
The Chianti countryside reveals itself in every direction. These towns and destinations are all within a thirty-minute drive — close enough for an afternoon escape, far enough to feel like a journey.
Panzano in Chianti
Home of Dario Cecchini, Italy's most famous butcher. His restaurants are a pilgrimage for meat lovers — the bistecca is legendary. The village itself is charming, perched above the Conca d'Oro valley.
15 min · Dario Cecchini · BisteccaGreve in Chianti
A lively market town with a beautiful triangular piazza. The weekly Saturday market is where local chefs shop — pecorino, prosciutto, seasonal produce. Don't miss the Falorni macelleria, a butcher shop operating since 1729.
20 min · Saturday Market · Falorni since 1729Castellina in Chianti
A fortress town with Etruscan tombs beneath medieval streets. Walk the Via delle Volte — a tunnel-street carved into the ancient walls — and stop for lunch with views across the valley.
15 min · Etruscan Heritage · Via delle VolteVolpaia
A fortified medieval hamlet turned wine estate. The entire village is essentially a winery — cellars run through tunnels beneath the stone houses. Taste their Chianti Classico Riserva in the village square.
10 min · Medieval Wine VillageThe Concierge
Every stay at Le Rondini is shaped by conversation, not catalogue. Tell us what moves you - a private museum visit, a vineyard tour, a birthday celebration beneath the Tuscan stars - and we will arrange the rest.