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.
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.
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:
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.
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.
Every traveller is different, so there is no such thing as the “best” Chianti villa; only the best Chianti holiday rental for you. When you contact Tuscany Now & More, you will talk to someone who has stayed at all your favourite villas. It’s our golden rule — and why we stick to a focused, specialist portfolio of around 130 handpicked villas.
If you have a picture of classic Tuscany in your head, the Chianti is where you will find it. Our Chianti holiday rentals include Renaissance villas and luxury stone farmhouses converted with sympathetic contemporary interior designs. As long as villa rentals in Italy have been popular, travellers have visited the Chianti.
Many properties in our special selection of villas in vineyards are in the Chianti. These offer you the opportunity to stay on renowned Chianti wine estates, tasting fruits harvested just over the garden wall and oak-aged in nearby cellars.
At the northern tip of the Chianti, Florence has even more sights, things to see and do, and places to shop. It is the regional capital. In and around Florence are the Uffizi Gallery; Michelangelo’s “David”; Medici villas, palaces and tombs; Renaissance gardens; countless painted chapels and much more. Equally art-rich and convenient for day-tripping are Siena and the preserved medieval town of San Gimignano.
Still undecided on your perfect Chianti villa? Read our guide to choosing the right villa in Italy.
Spring temperatures are usually pleasant with clear skies over most of Tuscany, including the Chianti. By late Spring, you should expect an average daytime high of 23℃ (73℉) and lows of 11℃ (51℉) overnight. Major May festivals in the Chianti include Barberino in Fiore, a flower festival held in Barberino Val d’Elsa, and the national Cantine Aperte open wine-cellars event.
Summer is high season almost everywhere, including the Chianti. The daytime temperature rises to an average high of 30℃ (86℉), with 17℃ (62℉) overnight typical. This is the ideal season for relaxing by your private pool, especially during the heat of the day.
You can also sample a genuine slice of local life by attending a “sagra” while you’re in the Chianti. These small village festivals usually take place on summer afternoons and evenings. They are advertised on posters around the area. For a small fee, there is food, live music, local wine and old-school dancing till late.
Despite cooler temperatures, autumn and winter are lots of fun around the Chianti. The sun shines most days, with an average daytime high of 13℃ (55℉) and overnight lows of 4℃ (39℉).
Early autumn has Chianti’s best-known grape harvest festival, the Expo del Chianti Classico. Over one long weekend in September, there are guided tastings plus live music and other wine-related events.
If you are interested in learning more about what makes us different, you can read the Tuscany Now & More story.
Everyone renting a Chianti villa with Tuscany Now & More gets free, unlimited access to our concierge service. If you want shopping stocked in your fridge on arrival, or a private chef to cook dinner for someone’s birthday or anniversary, just ask. Making your holiday lettings extra-special is part of our service. While you are in Italy, our 24-hour ground staff are available on the phone or WhatsApp.
Checking in & out
You should check in at your Chianti holiday rental between 4pm and 7pm. We can accommodate different arrival times — just communicate this in advance to our office staff. Upon arrival, the villa owner or caretaker will inspect the property with you and demo appliances, equipment and utilities.
Check-out is 10am on the last day of your holiday rental. The villa owner or caretaker will arrive at 9am to settle outstanding payments, if you have any. If you want to leave earlier, just let us know in advance.
Both your luxury Chianti villa and its private swimming pool are cleaned prior to your arrival. Some holiday villas have additional cleaning and pool/garden maintenance scheduled during the week. Maid service included with vacation rentals involves cleaning and tidying, but does not cover making beds, kitchen cleaning, laundry or ironing. Extra services can be organised with our dedicated travel concierge team.
Bed linen & towels
Our Chianti holiday rentals include bed linens, bathroom and swimming pool towels for all guests. These are provided weekly. Extra services and changes can be organised via our concierges.