The minute you see it, you sense Siena is a place frozen in time. These first impressions are right: a time-traveller from medieval Tuscany could still find their way around its centre, and would quickly recognize the scalloped-shaped Campo. Siena’s streets have barely changed since the 1300s
Siena is best known for Italy’s most thrilling annual festival. On two summer days each year — July 2nd and August 16th — jockeys representing ten of the city’s 16 neighbourhoods race horses bareback, and at breakneck speed, on a dirt track built around the main square. First place sets up a week-long party in the neighbourhood. Second is nowhere. This is the famous Palio.
At Palio time, Siena becomes one giant living pageant. The rest of the year, it’s one of Europe’s most magically preserved old cities.
Our Siena villas include luxury houses with a view of Siena’s skyline from your pool. We have large converted farmhouses suited to a family gathering in the Tuscan hills. Almost all of our villas near Siena have air-conditioned bedrooms, which you’ll appreciate in Tuscany’s long, warm summer.
Like every Tuscany Now & More property, each of our villas near Siena has a private swimming pool and free use of our expert concierge service. Your concierge can arrange a private chef, daily maid service, or your villa fridge stocked in time for your arrival. Our ground staff are available by phone or WhatsApp while you are staying at your Siena villa.
At Tuscany Now & More we take pride in our service. For 30 years we have been finding guests their ideal villa in Italy. Someone from our team visits or stays in every Siena villa we list. We know the area intimately. 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.
To also read what real travellers think of our service, and the experience of staying in a Tuscany Now & More luxury villa, check our verified reviews.
Siena is a remarkable small city — an enchanting place to discover for a first-time visitor to Tuscany, but also a trove of hidden corners to reward even our regular return visitors.
From a distance, looking across the hills of central Tuscany, it looks like a fairytale in red brick snaking along and around several high ridges. You can see the 102m/335-ft. turret of its Torre del Mangia for miles in any direction.
The Campo is the heart of the town, one of Europe’s most photogenic squares, and twice each summer host to the Palio. The rest of its compact, pedestrian centre is stuffed with Gothic palaces, ethereal art and locals who love their cakes, biscuits and other sweet treats.
The countryside drives and cycle rides in this part of Tuscany are among the region’s best.
Just remember to spell Siena with one “n”. The colour is sienna; the city is Siena. And you’ll love it.
Your first key photo stop in Siena is Piazza del Campo — “Il Campo”. Legend (and marketing) will tell you this is one of Italy’s most beautiful squares. If anything, that is an understatement. Whatever you’ve heard, or the pictures you’ve seen, nothing prepares you for the first time.
Its unique scallop-shaped design of herringboned brick was laid out in the 1320s, at the peak of Siena’s wealth and power. It is divided into 9 sections in recognition of “the Nine”, a republican governing council who ruled Siena from the 1280s to the 1350s — in the “common good” (in theory, anyway).
Siena’s medieval city hall, the Palazzo Pubblico, towers over the square. The inside is stuffed with art: frescoes by Simone Martini, sculpture by Jacopo della Quercia, and paintings by Siena’s many fine medieval and Renaissance artists, including Vecchietta and Matteo di Giovanni.
The city government met inside, and still does. Ambrogio Lorenzetti was commissioned to paint the room where they gathered, with a reminder of the civic virtues and a warning against vice. His massive creation is known as “The Allegories of Good and Bad Government” (1338), the greatest secular artwork of Italy’s Middle Ages.
Elsewhere around the centre, Siena’s cavern-like streets tunnel around a succession of medieval palaces, most built from local burnt-sienna brick. Behind a massive Gothic façade, Siena’s Duomo (Cathedral) is also filled with art treasures. Its floor is decorated with Bible scenes in inlaid marble created by generations of renowned Sienese artists. The whole project took two centuries to complete.
Art enthusiasts can dig deeper into Sienese art history at museums including Santa Maria della Scala, the Museo dell’Opera and the Pinacoteca Nazionale. These showcase the back-catalogue of great Sienese painters, including Duccio di Buoninsegna and the Lorenzetti brothers.
Sienese painters had a style all their own, separate from Renaissance “realism” practised in Florence. Painter Duccio (c. 1255–1318) was the founder of this Sienese School. Inside the Museo dell’Opera, his “Maestà” is the city’s most influential artwork. On the day Duccio completed it, it was carried in triumph from his studio on Via Stalloreggi to the cathedral high altar, where it remained for two centuries. Generations of local painters drew inspiration from it.
A door in the museum gives access up the Facciatone, the façade of a planned, never-completed extension to Siena’s cathedral. The steep, narrow climb to the lookut is not for vertigo sufferers… but views across terracotta rooftops to the Campo and hills beyond are epic.
South-east of the city, the hills of the Crete Senesi form one of Tuscany’s most recognizable landscapes. Roads wind along exposed ridges, ducking around cypress trees and lonely farmsteads, suddenly jerking left or right to avoid deep scars in the clay. Tour these hills on two wheels or four… and pack your camera.
The Sienese keep their bakers busy: the city has a major sweet tooth. Cantuccini (hard, almond-flour biscuits) are traditionally plonked on your table after a meal, with a serving of sweet, golden Vin Santo wine. However, cantuccini are originally from Prato, near Florence. Siena’s authentic equivalent are ricciarelli, baked here for centuries.
Cranking up your blood sugar is a dense honey, fruit, and nut cake called Panforte (a small slice is usually enough). Panpepato is similar but dusted with pepper and other spices.
Savoury cooking in Siena is simple and hearty, and makes plentiful use of Cinta Senese, a local breed of pig prized for succulent meat. Even a grilled “steak” of Cinta is a taste experience — and, in keeping with Sienese taste, gloriously sweet.
For shoppers, Siena’s centuries-old craftsmanship traditions survive in small stores and workshops on Via Stalloreggi, close to the cathedral. This street still houses many artisans working within the old town walls, just as it did when Duccio’s painting studio was here.
For a first-time visitor to Tuscany, Siena is one of the top-rank destinations. There are very few European medieval cities so well preserved. But this is no time capsule; Siena is alive with culture, food, wine and much more.
For cyclists, the hills around our Siena villas are magical for a day in the saddle: the SS438 to Asciano glows in the early morning and late afternoon light, as does the road south from there to San Giovanni d’Asso. A couple of our Siena villas sit right in this spectacular landscape.
Another reason to stay around Siena are its easy short-range daytrips. Renting a villa near Siena places you at the heart of Tuscany. The Chianti hills and winelands are just to the north, an easy, scenic drive through vineyards and olive groves. The Chianti is one of the most famous wine-growing areas in the world. As an alternative to a villa near Siena, you may also wish to browse our luxury Chianti villas.
The winelands of southern Tuscany, including Montepulciano and Montalcino, are a little farther away, but still within reach. You can see both, along with the Tuscan UNESCO landscape of the Val d’Orcia, in a one-day circuit by car.
Florence has the largest concentration of things to do in Tuscany. It is the region’s capital, with the Uffizi Gallery; Michelangelo’s “David”; Renaissance gardens; high-fashion shopping and more. It takes around 75 minutes to reach central Florence by car from most of our Siena villas. There is also a frequent, comfortable express bus link between Siena and Florence.
We have created guides to many more of the best small-town daytrips from our Siena villas. Bookmark the following for the next research phase of your trip:
Castellina in Chianti travel guide
Spring temperatures are pleasant over most of central Italy, including Siena. You should expect an average daytime high of 23℃ (73℉) and lows of 11℃ (51℉) overnight by late Spring.
Summer is high season in the hills around Siena. Afternoon temperatures typically climb to or beyond 30℃ (86℉), with 17℃ (62℉) overnight. The Palio di Siena horserace (July and August) is one of Italy’s iconic cultural events — and inspiration for one of the highest-rated movie documentaries on Rotten Tomatoes.
Speak to our concierges for advice on attending the Palio while you are here. It’s an unmissable summer event. Seasonal food festivals include August’s Watermelon Festival in nearby Castellina in Chianti.
Despite cooler temperatures, autumn and winter are still lots of fun around Siena. The sun shines most days, with an average high of 13℃ (55℉) and lows of 4℃ (39℉) overnight. Low season means you can enjoy the city and nearby wine villages at your own pace — with much thinner crowds. It’s often warm enough to schedule a cycle ride.
Our month-by-month detailed guide helps you pick your perfect time to travel to Tuscany: read When is the Best Time to Visit Tuscany.
If you are interested in learning what makes us different, you can read the Tuscany Now & More story.
Everyone renting a villa near Siena with Tuscany Now & More gets free use of our concierge service. If you want your fridge stocked on arrival, or a private chef to make an occasion extra-special, just ask. Making your holiday lettings memorable is all part of our service.
While you’re in Italy, Tuscany Now & More ground staff are available by phone or WhatsApp.
Checking in & out
You should check in at your Siena holiday rental between 4pm and 7pm. We can offer tailored arrival times; just communicate this in advance to our office staff. It takes about 90 minutes to drive from Pisa Airport to Siena. Certaldo or Colle Val d’Elsa makes a perfect coffee stop along the route. Rome’s main international airport is around 2 hours, 45 minutes away by car. The fastest route from Rome follows a toll freeway.
Upon your arrival, the Siena villa owner or caretaker inspects the property with you and demonstrates appliances, equipment and utilities.
Check-out is 10am on the last day of your Siena holiday rental. The villa owner or caretaker will arrive at 9am to settle any outstanding payments. If you want to depart earlier, you can let us know in advance.
Both the luxury villa and your private swimming pool will be cleaned prior to your arrival. Some of our holiday villas near Siena have additional cleaning and pool/garden maintenance scheduled during the week. Maid service included with vacation rentals involves cleaning and tidying, but not making beds, kitchen cleaning, laundry or ironing. Extra services can be organised via our dedicated travel concierge team.
Bed linen & towels
Our Siena holiday rentals include bed linens, bathroom and swimming pool towels for all guests. These are provided weekly. Extra services and changes can be organised pre-trip with our concierges.