Villa rentals in the Chianti
The hills between Florence and Siena — known as the Chianti — make up one of Italy’s most photogenic regions. Our villas in the Chianti give you a front row view of the vineyards, olive groves and quiet, scenic backroads of this unforgettable part of Europe.
The Chianti is not all countryside. Hill-towns dot the landscape, many with a history stretching back millennia. World-famous (and less-famous) wineries occupy old stone farmhouses and ancient abbeys. In every season, from spring’s zucchini flowers to autumn’s porcini mushrooms and winter truffles, weekly market day is an event. Many of our Chianti villas are an easy cycle ride or brisk walk away from the stalls.
At Tuscany Now & More we take pride in our service. We have 30 years’ experience matching each party of guests to their ideal villa. Someone from our expert team visits or stays in every Chianti villa we list, and knows the area. This is why we keep our portfolio small — and why the world’s leading luxury travel magazine says we’re Tuscany’s best villa company.
Every Tuscany Now & More villa has a private swimming pool, free use of our concierge service, for pre-trip arrangements and an emergency number available 24/7 while you are in-destination. Your concierge can arrange a private chef, daily maid service, or shopping delivered to your villa, and memorable experiences like Tuscan cookery classes in your holiday rental’s kitchen.
The villas in the Chianti listed below have from two to 12 bedrooms. In all except one, these are air-conditioned bedrooms — which you’ll appreciate in the warm Tuscan summer. To see what real travellers think of our service, and the experience of renting a Tuscany Now & More luxury villa, read our verified reviews.
About the Chianti
Even if you have never visited, the Chianti can feel familiar. The landscape is framed by the geometric patterns of vineyards and olive groves. Case coloniche — traditional stone farmhouses, many with dovecote turrets — pepper the horizon. An occasional church bell tower pokes above the vines. This landscape was a backdrop often used by Renaissance painters. They knew a pretty picture when they saw one.
Renting a villa here gives you a chance to escape and to relax. You are also within easy reach of Florence and Siena, with the sights and art of two iconic cities. Indeed, many of our villa rentals near Florence are also on the Chianti’s doorstep.
What to Do in the Chianti
The Chianti is big on scenery. Its backroads provide some of Tuscany’s classic drives. The main wine road, the SS222 or “Chiantigiana”, has panoramas along its entire length, from Florence’s suburbs south to Siena. At one of the most scenic spots, near Panzano, the Conca d’Oro (Golden Bowl) has rows of vines covering what appears to be a giant “scoop” dug from the hillside.
The SS429 is stunning between Poggibonsi and Castellina, and again between Radda and the Badia a Coltibuono winery. An unpaved strada bianca (literally “white road,” another feature of the landscape) between Greve and the main Siena–Florence road, past the lonely abbey at Badia a Passignano, is unforgettable.
Radda is the classic Chianti town. Crowning a hill amid a sea of vines, this sunny cluster of stone buildings and charming lanes seems almost piled up. The main “sight” inside the walls is its Palazzo del Podestà, built in the 15th century — then rebuilt after Spanish troops flattened it in 1478 — as the administrative centre of the region. Ceramic coats of arms decorate its façade.
It’s hard to believe now, but these peaceful hills were for centuries the front line in a conflict between the 2 great medieval powers of central Italy, Florence and Siena. Hence a castle crowns almost every high vantage point.
Several are now ruined, their stones poking above wild holm oak forests. A few have been taken over by modern wineries. They’re linked on the Strada dei Castelli di Chianti (Chianti Castle Road). Gaiole is a bit of a castle-hunters’ hot-spot.
The Chianti is spoilt for unforgettable views, but it’s hard to beat the outlook from the top of Castellina’s fortress. This fortified palace is now an Etruscan and wine museum. Climb to its roof and you quickly grasp why Castellina was such an important outpost for Florence in its tit-for-tat medieval conflict with Siena.
Radda, Castellina and many more Chianti hill-towns are a delight just to wander — plus there’s always fresh gelato for the kids (and adults).
For more ideas on things to do in the Chianti, including the best wineries to visit near several Chianti towns and villages, read some of our Chianti village guides:
- Greve in Chianti travel guide
- Radda in Chianti travel guide
- Gaiole in Chianti travel guide
- Castellina in Chianti travel guide
- Barberino Val d’Elsa travel guide
- San Polo in Chianti travel guide
- Impruneta travel guide
Food & Drink in the Chianti
Chianti is a is gastronomic paradise. If you love great food, seasonal produce and fine wine, you are coming to the right place.
These are some of the world’s most famous winelands. Chianti wine rules date back to 1716, when this region became the first regulated wine area in Italy. When first demarcated in 1716, Chianti included only three villages: Gaiole, Castellina and Radda. Having adopted the Gallo Nero (black rooster) as its symbol, in 1932 the growing zone was redrawn and subdivided into 7 areas (now 8).
Each sub-zone creates a unique Chianti wine, with differences including how long they age, alcohol levels, and which dishes they complement. Growing zones to look for on labels are Classico, the oldest part in the heart of Chianti hills; Rufina, around the comune of Rufina, on the southern edge of the Mugello; and Montespertoli, established in 1996, with the town of the same name at its centre.
The main fruit in them all is the Sangiovese. This red grape has characteristics which set it apart. Ruby red in appearance, it has unique aromas and firm tannins, and is high in acidity. The feel of a Sangiovese wine in your mouth is neither powerful nor delicate, but balanced. The young grape exhibits aromas of cherry, violets, plums and blueberries. With age it can develop sweet tobacco, coffee, and spices.
Travellers with a deep interest in wine should speak to our award-winning concierges, who can arrange a wine tour of some of the finest Chianti estates or a sommelier-led tasting in your villa kitchen. If you want to stay even closer-up with the vines, you should also browse our collection of villas in vineyards in Italy, many of them in the Chianti.
As well as wine, Chianti is known for its olive oil. Over 400,000 silver-green olive trees grow across the region. Like the region’s wine, Chianti extra-virgin oil is regulated and awarded DOP status for quality assurance.
Fresh produce is part of everyday life in the Chianti, spiritual home of la cucina toscana. Traditional Chianti cooking does not need complex processes typical of “fine dining”. It allows local ingredients to sing.
Classic starters include panzanella, a salad of tomatoes, basil, and yesterday’s bread soaked in Tuscan olive oil; and pappa al pomodoro, a thick tomato soup-stew.
Carnivores are in luck, because this area is also famed for butchers, who sell both raw cuts such as bistecca alla fiorentina (“Florentine”, large bone-in steak) and cured meats. Look out for salami made from Cinta Senese, a native breed of pig with sweet-ish meat. Wild boar salami (salami di cinghiale) is another Chianti speciality. Two favourites among many first-rate Chianti butchers are Secci in Strada and Falorni in Greve.
For the complete food experience on your Chianti vacation, check out our cooking vacations in Tuscany — both based at luxury Chianti villas. To secure table reservations at the finest Chianti restaurants, you can also just ask our expert Tuscany travel concierges.
You should also check the information booklet in your Chianti villa for details of local markets — they are not to be missed.
Shopping in the Chianti
Above all, this is the place to buy Tuscan wine and single-estate olive oil. Pretty much everywhere reputable will ship your purchases home for a reasonable fee. The Sangiovese grape rules — and is the main ingredient in a fine Chianti. Olives squeezed each November produce a pale, pungent oil prized for very low acidity.
As well as wine and olive oil, the Chianti region is renowned for its handicrafts — everything from leather to terracotta to wood-carvings are still created in tiny workshops. Walk into almost any small town and you will encounter a cobbled street with small-scale vendors or even an open workshop to browse.
Hand-painted glazed ceramics are very closely associated with the Chianti. Among many renowned workshops is Rampini near Gaiole. Their bold, colourful designs typically feature motifs inspired by the Tuscan countryside.
Impruneta terracotta — cotto dell’Impruneta — is made from a porous, iron oxide-rich clay and has been famous since at least the 11th century. Impruneta terracotta tiles adorn Brunelleschi’s cathedral dome in Florence. Town workshops welcome visitors.
You are also within easy driving distance of a couple of the best luxury outlet malls in Tuscany. The Mall and The Space (Prada’s outlet) are both in the Valdarno area, just east of the Chianti.
