Why Stay in Siena?
Siena is the medieval soul of Tuscany — a city that refused to become a Renaissance theme park and instead preserved its Gothic identity with a fierce, contrade-driven civic pride that remains unmatched in Italy. While Florence embraced the Renaissance and the Medici, Siena held fast to its medieval character, and the result is a city that looks, feels, and functions much as it did in the 13th and 14th centuries, when it rivalled Florence as the most powerful city-state in central Italy. The entire historic centre has been a UNESCO World Heritage Site since 1995, recognised for its extraordinary medieval urban fabric and the quality of its Gothic architecture.
The city is built across three steep hills, connected by a web of narrow brick-paved lanes, arched passageways, and stone staircases that open suddenly onto breathtaking views of terracotta rooftops, the surrounding Tuscan countryside, and the distinctive black-and-white marble of the Duomo. At the convergence of the three hills sits Piazza del Campo — universally regarded as one of the most beautiful public squares in the world. Shaped like a tilted scallop shell and divided into nine segments representing the medieval Council of Nine, the Campo slopes gently downward toward the Palazzo Pubblico and its soaring 102-metre Torre del Mangia. It is here, twice each summer, that the Palio takes place — a bareback horse race around the piazza's perimeter that is not a tourist spectacle but a living, breathing expression of Sienese identity that has continued unbroken since 1644.
Siena is defined by its 17 contrade — historic neighbourhoods, each with its own animal emblem, colours, church, museum, fountain, and fiercely loyal residents. The contrade system is not a quaint relic; it is the active social fabric of the city. Sienese are baptised into their contrada, socialise within it, celebrate its victories, and mourn its defeats. Walking through the streets, you will spot ceramic plaques, painted emblems, and coloured streetlights marking the boundaries between the Oca (Goose), the Torre (Tower), the Pantera (Panther), the Selva (Forest), and the other thirteen contrade. Each maintains a small museum open to visitors, and the contrada fountains — ornate marble drinking troughs for the Palio horses — are works of art in their own right.
The Duomo di Siena is one of Italy's most extraordinary cathedrals — a riot of black-and-white striped marble, both inside and out, that reflects the city's heraldic colours (the balzana, the black-and-white shield). Inside, the inlaid marble floor contains 56 panels of biblical and allegorical scenes created over two centuries by more than 40 artists — a masterpiece usually covered by protective boards and fully revealed only from mid-August to mid-October. The Piccolomini Library within the cathedral dazzles with Pinturicchio's frescoes depicting the life of Pope Pius II. Nicola Pisano's hexagonal pulpit, carved between 1265 and 1268, is among the finest examples of Gothic sculpture in existence. The Museo dell'Opera del Duomo next door houses Duccio di Buoninsegna's Maestà (1308–1311), the greatest masterpiece of Sienese painting and one of the most important works of medieval art.
Beyond its monuments, Siena is a sensory experience. The scent of roasting coffee drifts from bars along Via Banchi di Sopra. Bakeries sell ricciarelli — soft almond biscuits dusted with icing sugar — and slabs of panforte, the dense, spiced fruit-and-nut confection that has been made in Siena since the 13th century. Restaurants serve pici, the thick hand-rolled pasta unique to the Siena province, dressed with garlic-and-breadcrumb aglione sauce or slow-cooked wild boar ragù. The city sits at the northern edge of the Brunello di Montalcino and Vino Nobile di Montepulciano wine regions, and at the southern fringe of Chianti Classico — making it one of the finest wine destinations in Italy.
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Siena at a Glance
Getting there: Siena does not have its own airport. The nearest major airport is Florence Airport (FLR), 68 km north, followed by Pisa Airport (PSA), 130 km northwest. From Florence, the fastest connection is the Tiemme/SITA direct bus from the Autostazione (near Santa Maria Novella station), taking approximately 75 minutes and running roughly every 30 minutes. Trains from Florence to Siena via Empoli take 90–120 minutes with a change, and Siena's railway station sits about 2 km downhill from the centre (connected by escalators and minibuses). By car, the toll-free Firenze-Siena superstrada (RA3/SGC) takes about 75 minutes. The historic centre is a strict ZTL (zona a traffico limitato) — park in one of the large car parks outside the walls (Il Campo, Stadio, Santa Caterina) and walk or take the minibus into the centre.
Getting the Most from Your Visit
Getting Around
Siena's historic centre is compact — roughly 1.5 km from end to end — and almost entirely car-free, making it one of the most pleasant walking cities in Italy. That said, the city is built on three hills, and the terrain is genuinely steep in places. The main streets — Via Banchi di Sopra, Via Banchi di Sotto, and Via di Città — follow the ridgelines and are relatively flat, but stepping off these into the side lanes means navigating stone staircases, steep ramps, and sharp inclines. Wear comfortable shoes with good grip; the brick-paved streets can be slippery when wet. For those who prefer to avoid the steeper climbs, Siena operates a network of small electric minibuses (called pollicini) that circulate through the centre and connect the car parks to the main piazzas. These are included in the standard bus ticket (€1.30 for 70 minutes).
Best Time to Visit
The ideal months are April to June and September to October, when temperatures range between 15°C and 28°C and the light over the Sienese hills is at its most beautiful. The Palio races on 2 July and 16 August are extraordinary cultural events but bring massive crowds — the piazza holds up to 40,000 spectators, and hotel prices spike. If you want to experience the Palio, book accommodation at least three to four months ahead. July and August are hot (often above 33°C), though Siena's hilltop location and stone buildings provide some natural cooling. Winter (November to February) is quiet, atmospheric, and excellent value — the city belongs to locals, the restaurants are unhurried, and the Duomo's marble floor panels are fully uncovered in late summer through mid-October. Siena's Christmas market and New Year celebrations bring modest but festive crowds.
Passes and Tickets
The Opa Si Pass (also known as the Duomo complex ticket) covers the cathedral, Piccolomini Library, the Museo dell'Opera del Duomo, the Baptistery, the Crypt, and the panoramic viewpoint from the Facciatone (the unfinished nave wall) — excellent value at around €15 and valid for three days. The Museo Civico inside Palazzo Pubblico and the Torre del Mangia are ticketed separately. Entry to Piazza del Campo itself is always free. Most contrada museums open by arrangement or during special events — ask at the contrada headquarters if you are interested.
Where to Stay in Siena
Siena is small enough that staying anywhere in the historic centre puts you within walking distance of everything. The neighbourhoods each offer a different feel:
Terzo di Camollìa is the northern third of the city, stretching from Porta Camollìa — the historic gateway from Florence, still inscribed with the famous motto "Cor magis tibi Sena pandit" (Siena opens her heart to you wider than this gate) — down through Via Banchi di Sopra past Piazza Salimbeni toward the Campo. This is the commercial heart of the city, home to shops, banks (including the headquarters of Monte dei Paschi di Siena, the world's oldest bank, founded in 1472), and many of the best restaurants. The Fortezza Medicea, a 16th-century fortress now used for wine tastings and cultural events, sits at the northern edge. Hotels here tend to be well-connected and practical, with easy access to the bus terminal and car parks.
Terzo di Città is the central and western third, encompassing both the Duomo and Piazza del Campo. This is the most atmospheric area — winding medieval lanes, the cathedral precinct, the Pinacoteca Nazionale, and the views from the Facciatone. Hotels in this area occupy historic palazzi with centuries of character, and you are steps from the main sights. The trade-off is noise (especially during the Palio season) and the steepest terrain in the city.
Terzo di San Martino is the quieter southern third, stretching from the Campo down toward Porta Romana and the Basilica dell'Osservanza. This area has a more residential feel, with local shops and less tourist traffic. Several excellent hotels sit just inside or outside Porta Romana, offering garden settings and countryside views that the dense centre cannot provide. It is a 10-minute walk uphill to the Campo from here.
Outside the Walls — the rolling hills immediately surrounding Siena offer boutique agriturismi and relais with swimming pools, olive groves, and panoramic views of the city skyline. These are ideal for travellers with a car who want the Tuscan countryside experience with the city a short drive away. Parking is straightforward, and the views at sunset — the silhouette of the Torre del Mangia and Duomo against a golden sky — are unforgettable.
Eco-Friendly Hotels in Siena
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Grand Hotel Continental Siena — Starhotels Collezione ★★★★★
The only five-star hotel within Siena's historic walls, the Grand Hotel Continental occupies a magnificent 17th-century palazzo on Via Banchi di Sopra — the city's main thoroughfare. Originally built for the Chigi-Saracini noble family, the building retains its original frescoed ceilings, stucco work, and Murano glass chandeliers throughout the public areas and many of the 51 rooms. Suites overlook the terracotta rooftops and the countryside beyond. The Winter Garden restaurant serves refined Tuscan cuisine beneath a glass-roofed atrium. Piazza del Campo is a two-minute walk. This is the most prestigious address in the city — a genuine palazzo experience with Starhotels' polished service standards.
Hotel Athena ★★★★
Hotel Athena earns its reputation for one of the finest views in Siena. Set on the western edge of the historic centre near the Duomo, many of its 100 rooms and suites look out over the Duomo's marble façade and the rolling green Tuscan countryside beyond — a vista that is particularly spectacular at sunset. The rooftop terrace and restaurant capitalize on this panorama, offering Tuscan dishes alongside a view that stretches to the distant hills of the Crete Senesi. The hotel is modern and well-maintained, with a private car park (a genuine luxury in Siena's medieval centre) and a short walk to both the Duomo and Piazza del Campo. The swimming pool and garden provide a welcome retreat after a day of sightseeing.
Hotel Santa Caterina ★★★
Tucked just outside the southern city gate of Porta Romana, Hotel Santa Caterina offers a peaceful setting with a terraced garden that drops away toward the Val d'Orcia — the views from the breakfast room and garden are genuinely remarkable. The 22 rooms are simply but comfortably furnished in a classic Tuscan style, with terracotta floors and wooden furniture. The location, while technically outside the walls, puts you at Porta Romana — from here it is a pleasant 10-minute walk uphill along Via Roma to Piazza del Campo, passing through the Terzo di San Martino. The garden, shaded by cypresses and flowering plants, is a tranquil spot for reading or an aperitivo. One of Siena's best value options for the quality of setting.
Hotel Palazzo Ravizza ★★★★
A genuine Renaissance palazzo that has been in the same family since the 1920s, Palazzo Ravizza combines historic character with the warmth of a family-run hotel. The 40 rooms are furnished with antiques, original oil paintings, and period furniture — no two rooms are alike. The real jewel is the private garden: a large, peaceful green space with old trees, a gravel terrace, and panoramic views over the Tuscan countryside that feels worlds away from the medieval streets just outside the front door. The palazzo sits on Pian dei Mantellini, a quiet street in the Terzo di Città, a five-minute walk from Piazza del Campo and three minutes from the Duomo. The library, filled with leather-bound books and comfortable armchairs, invites afternoon reading. Breakfast is served in a frescoed dining room.
Hotel Italia ★★★
A practical, well-run three-star hotel on Viale Cavour, just a short walk from Siena's railway station and the escalators that carry passengers up into the historic centre. Hotel Italia offers 57 clean, modern rooms at competitive prices — this is the sensible choice for travellers arriving by train or those who want straightforward accommodation without paying a premium for a historic centre address. The décor is simple and contemporary, rooms are air-conditioned, and there is a small bar and breakfast room. The escalator from Viale Cavour up to Piazza Antonio Gramsci takes about five minutes, and from there it is a short walk to the Campo. The surrounding area has supermarkets, pharmacies, and local restaurants at non-tourist prices.
NH Siena ★★★★
Part of the NH Hotels chain, NH Siena occupies a modern building on Piazza La Lizza at the northern edge of the historic centre, adjacent to the Fortezza Medicea and the Enoteca Italiana (Italy's national wine cellar, housed within the fortress vaults). The 124 rooms follow the NH group's clean, contemporary design language — functional, well-maintained, and reliably comfortable. What sets this location apart is the proximity to the Fortezza and its wine-tasting opportunities, the La Lizza gardens, and the Wednesday market that fills the piazza. The hotel has a car park, a genuine advantage in car-free Siena, and is a 10-minute walk from Piazza del Campo via Via Banchi di Sopra. A solid four-star choice for those who prefer modern amenities over medieval charm.
Frances' Lodge Relais ★★★★
A boutique relais set in the gentle hills just south of Siena's walls, Frances' Lodge is a Tuscan dream realised in stone, gardens, and panoramic countryside views. The property — a restored farmhouse surrounded by olive trees and manicured gardens — offers just a handful of individually decorated rooms and suites, each furnished with antiques and opening onto garden or countryside views. The swimming pool overlooks a rolling landscape of vineyards and cypress trees, with the towers of Siena visible on the horizon. Breakfast is served in the garden when weather permits. The city centre is about a 15-minute drive or a 30-minute walk along country lanes. This is the choice for travellers who want the quintessential Tuscan countryside experience within reach of a great medieval city.
Pensione Palazzo Ravizza ★★★
Sharing the same historic building as its four-star sibling, the Pensione Palazzo Ravizza offers a more affordable way to experience this Renaissance palazzo. The pensione rooms are smaller and more simply furnished but retain the character of the building — high ceilings, wooden shutters, and views over the garden or the city. Guests share access to the palazzo's magnificent garden terrace with its countryside panorama, and the same warm, family-run hospitality applies. The location on Pian dei Mantellini is quiet yet central — five minutes on foot to the Campo, three to the Duomo. For budget-conscious travellers who want history and atmosphere without the four-star price tag, this is one of Siena's best-kept accommodation secrets.
Things to Do in Siena
Piazza del Campo
Widely considered one of the most beautiful public squares in the world, Piazza del Campo is the heart of Siena in every sense — geographic, social, and emotional. The piazza takes the form of a gently sloping scallop shell, paved in red brick and divided into nine segments by lines of white travertine stone, representing the medieval Council of Nine (Governo dei Nove) that ruled Siena during its golden age in the 13th and 14th centuries. The shell shape is not just aesthetic — it was engineered to channel rainwater to a central drain. At the base of the shell stands the Palazzo Pubblico with its soaring Torre del Mangia; at the top, the elegant Fonte Gaia fountain (a 19th-century replica of Jacopo della Quercia's 1419 original, now in the Museo Civico). Locals and visitors alike sprawl across the warm brick in the afternoon sun, making the Campo a giant open-air living room. Twice each summer, the piazza transforms into a racetrack for the Palio.
Palazzo Pubblico & Torre del Mangia
Siena's Gothic town hall, completed in 1310, is both a functioning municipal building and one of the finest art museums in Tuscany. The Museo Civico on the upper floors contains Ambrogio Lorenzetti's Allegory of Good and Bad Government (1338–1339) — a vast fresco cycle that is one of the most important secular paintings of the Middle Ages, depicting the effects of just and unjust rule on a recognisably Sienese landscape. Simone Martini's Maestà (1315) fills an entire wall of the council chamber. The Torre del Mangia, at 102 metres, was the second-tallest tower in medieval Italy and offers staggering views of the city and surrounding countryside from its narrow summit platform — reached via 400 steep steps through the tower's interior. Visitor numbers to the tower are limited, so arrive early or book ahead during peak season.
Duomo di Siena
Siena's cathedral is an overwhelming masterpiece of Italian Gothic architecture. The exterior is a confection of black-and-white striped marble (representing the colours of the balzana, Siena's heraldic shield), pink marble, and elaborate sculptural decoration. Inside, the alternating black-and-white marble columns create a dramatic, almost hypnotic effect. The marble floor is the cathedral's greatest treasure — 56 panels of intricate inlaid marble work depicting biblical scenes, sibyls, and allegories, created by more than 40 artists over two centuries (1369–1547). Most panels are covered by protective boarding and only fully revealed from mid-August to mid-October; visiting during this window is worth planning your trip around. The Piccolomini Library, accessible from the left nave, blazes with Pinturicchio's brilliantly preserved frescoes (1502–1507) depicting ten episodes from the life of Pope Pius II (Enea Silvio Piccolomini), a native of nearby Pienza. Nicola Pisano's pulpit (1265–1268), supported by columns resting on lions and carved with scenes from the life of Christ, is one of the supreme achievements of Gothic sculpture.
Museo dell'Opera del Duomo
Housed in the right aisle of the cathedral's unfinished nave extension (the Duomo Nuovo, abandoned after the Black Death of 1348 killed more than half the city's population), this museum contains the masterpieces too fragile or precious for the cathedral itself. The centrepiece is Duccio di Buoninsegna's Maestà (1308–1311) — a monumental double-sided altarpiece that was originally carried from Duccio's studio to the cathedral in a citywide procession. The front panel depicts the Virgin and Child enthroned among saints; the reverse contains 26 scenes from the Passion of Christ, each painted with an intimacy and emotional depth that revolutionised Italian art. Jacopo della Quercia's original Fonte Gaia panels are also here, along with works by Giovanni Pisano. From the museum, a staircase leads up to the Facciatone — the top of the unfinished nave wall — offering a breathtaking panoramic view across the city and out to the Tuscan horizon.
Pinacoteca Nazionale
Siena's national picture gallery, housed in the 14th-century Palazzo Buonsignori on Via San Pietro, contains the most comprehensive collection of Sienese painting in existence — tracing the distinctive Sienese school from the 12th to the 17th century. While less famous internationally than Florence's Uffizi, the Pinacoteca is essential for understanding the unique artistic tradition that developed in Siena, characterised by elegant line, luminous colour, and gold-ground compositions that looked to Byzantine models while developing a distinct Gothic sensibility. Highlights include works by Duccio, Simone Martini, Pietro and Ambrogio Lorenzetti, Sassetta, and Giovanni di Paolo. The gallery is rarely crowded, making it one of Siena's most rewarding museum experiences.
Basilica di San Domenico
This austere Gothic basilica, perched on a hill overlooking the Fontebranda valley, is one of Siena's most important churches — primarily because of its association with Saint Catherine of Siena (1347–1380), the mystic, theologian, and Doctor of the Church who is Siena's patron saint and co-patron of Italy and Europe. The Chapel of Saint Catherine contains her preserved head in a gilded reliquary — a macabre but deeply significant relic. The chapel walls are decorated with frescoes by Sodoma (Giovanni Antonio Bazzi) depicting scenes from Catherine's life, including her famous mystical ecstasy and stigmata. The basilica's massive brick exterior, dominating the skyline from the west, is one of the most recognisable views of Siena — and the terrace in front offers excellent panoramic views toward the Duomo.
Santa Maria della Scala
Directly opposite the Duomo's main entrance, this enormous complex served as Siena's main hospital for over a thousand years — from the 9th century until the 1990s. It has been brilliantly converted into a museum and cultural centre. The highlight is the Pellegrinaio (Pilgrims' Hall), where a stunning cycle of 15th-century frescoes by Domenico di Bartolo depicts the daily operations of the medieval hospital — caring for the sick, feeding the poor, raising orphans — in vivid, documentary detail that is both art and social history. The underground levels contain the Oratorio di Santa Caterina della Notte (a small chapel where Saint Catherine prayed through the night) and an archaeological museum with Etruscan artefacts from the surrounding province. Temporary exhibitions of contemporary art fill the upper halls, creating an engaging dialogue between medieval and modern.
Fortezza Medicea
Built by Cosimo I de' Medici in 1561 after the fall of the Sienese Republic, this star-shaped fortress at the northern edge of the city was intended to intimidate the conquered population — but today it serves a far more pleasant purpose. The Enoteca Italiana, housed in the fortress vaults, is Italy's national wine cellar, offering tastings of wines from across the country in an atmospheric brick-vaulted setting. The fortress ramparts are a popular walking circuit with views over the La Lizza gardens and the northern countryside. In summer, the interior courtyard hosts open-air concerts, jazz festivals, and cinema screenings. The adjacent La Lizza gardens are a pleasant public park with shaded paths and a Wednesday morning market.
Piazza Salimbeni & Monte dei Paschi di Siena
This elegant crescent-shaped piazza at the top of Via Banchi di Sopra is flanked by three palazzi — the Gothic Palazzo Salimbeni, the Renaissance Palazzo Spannocchi, and the Baroque Palazzo Tantucci — which together form the headquarters of Monte dei Paschi di Siena, the oldest continuously operating bank in the world, founded in 1472. The bank began as a charitable institution lending money at low interest to Siena's poor and funded by the revenues of the city's pasture lands (paschi). A statue of the economist Sallustio Bandini stands in the centre of the piazza. The bank's history museum (occasional exhibitions) and the architectural ensemble itself are worth the visit — this is living economic history stretching back over 550 years.
Orto Botanico dell'Università di Siena
Siena's botanical garden, maintained by the University of Siena since 1784, occupies a peaceful valley below the Terzo di San Martino, wedged between the city walls and the surrounding countryside. The garden contains over 2,000 plant species organised by geographic origin and botanical family, with a particular focus on Tuscan native flora and medicinal plants. The setting — a green oasis hidden below the medieval walls, with the Duomo visible above the tree canopy — is unexpectedly beautiful and almost never crowded. It is a perfect retreat from the summer heat and tourist bustle of the centre. Open daily except Monday; entry is a few euros.
The Palio di Siena
The Palio is not a tourist attraction — it is the single most important cultural event in Sienese life, a bareback horse race around Piazza del Campo that embodies centuries of contrada rivalry, civic identity, and raw, unfiltered emotion. Two races are held each year: the Palio di Provenzano on 2 July (dedicated to the Madonna of Provenzano) and the Palio dell'Assunta on 16 August (dedicated to the Assumption of Mary).
Ten of Siena's 17 contrade participate in each race — the seven that did not run in the previous year's corresponding race, plus three chosen by lot. The horses are assigned to contrade by lottery, and the jockeys ride bareback at terrifying speed around a temporary dirt track laid over the piazza's brick paving. The race itself lasts approximately 90 seconds — three laps of the Campo — but the build-up spans four days of trial races, processions, contrada dinners, horse blessings (in the contrada churches), and steadily mounting tension. On race day, the piazza fills with up to 40,000 spectators standing in the centre of the Campo (free, first-come) or watching from rented balcony seats (expensive, booked months ahead). The start is deliberately chaotic — the horses line up behind a rope at the mossa (starting point), and the race begins when the starter drops the rope, often after multiple false starts that can last over an hour.
The tradition dates to 1644 in its current form, though horse races in Siena's piazzas go back to at least the 13th century. Winning the Palio brings joy that can last years; rival contrade conspire through partiti (deals and alliances) to influence outcomes. The winning contrada celebrates with weeks of banquets and processions. If you visit during the Palio, expect a city transformed by passion, noise, colour, and a collective fervour that has no real equivalent anywhere else in Europe.
Recommended Walks
🏛️ Historic Centre — Campo to Duomo to San Domenico
Distance: ~2 km | Time: 1 hour | Difficulty: Easy (but hilly)
Begin at Piazza del Campo, absorbing the shell-shaped piazza and the Palazzo Pubblico before climbing Via di Città — Siena's elegant main street lined with medieval palazzi, artisan workshops, and tempting bakeries selling ricciarelli and panforte. Pass through Piazza del Duomo, where the black-and-white cathedral dominates the skyline. If time allows, step inside for the Piccolomini Library frescoes and the inlaid marble floor. Continue along Via della Sapienza, descending past the University of Siena's historic buildings to the Basilica di San Domenico, the austere Gothic church housing the relic of Saint Catherine's head. The terrace in front of San Domenico offers one of the best panoramic views in Siena — the Duomo and Torre del Mangia rising above a sea of terracotta rooftops. Return via the Fontebranda, Siena's oldest fountain (mentioned by Dante in the Inferno), and climb back up through narrow contrada lanes to the Campo.
🐎 Contrade Discovery Walk — Fountains and Emblems
Distance: ~4 km | Time: 2 hours | Difficulty: Moderate (steep sections)
Explore the living contrada system by visiting at least five contrade, spotting their emblems, colours, and ornate fountains. Start in the Contrada dell'Oca (Goose) near Fontebranda, where ceramic goose plaques adorn the buildings and the contrada fountain features a carved goose. Head south through the Contrada della Torre (Tower), identifiable by the elephant-and-tower emblem on its streetlights and buildings. Cross into the Contrada della Selva (Forest), marked by a rhinoceros emblem — one of the most unexpected heraldic symbols in Italy, dating to a 16th-century gift of a rhinoceros to the city. Continue to the Contrada della Pantera (Panther), with its striking panther-head fountains, then finish in the Contrada della Chiocciola (Snail) in the southern quarter, where the small contrada museum is often open for visitors. Along the way, notice how the streetlights, drainpipes, and even rubbish bins change colour as you cross contrada boundaries. Each contrada has its own headquarters (sede), church, and social club — ask at the sede about visiting the contrada museum.
⛪ Siena to Monteriggioni via the Via Francigena
Distance: ~15 km | Time: 4–5 hours | Difficulty: Moderate
Follow the ancient Via Francigena — the medieval pilgrimage route from Canterbury to Rome — northward from Siena to the perfectly preserved walled village of Monteriggioni. The walk begins at Porta Camollìa, Siena's northern gate, and descends through olive groves and farmland into the rolling Sienese countryside. The path is well-marked with red-and-white Via Francigena signs and passes through open fields, small woodlands, and quiet country lanes. After about 12 km, the 14 towers of Monteriggioni appear on the horizon — Dante mentioned them in the Inferno, comparing them to the giants guarding the pit of Hell. The village, enclosed within perfectly intact 13th-century walls, is a single circular street with a central piazza, a Romanesque church, and a handful of restaurants and cafés. The walls are climbable, offering views over the Chianti countryside. Return to Siena by local bus (about 30 minutes) or continue the Via Francigena onward toward San Gimignano.
🌙 Le Crete Senesi Loop from Asciano
Distance: ~10 km | Time: 3 hours | Difficulty: Moderate
The Crete Senesi — the clay hills southeast of Siena — is one of the most otherworldly landscapes in Italy. Pale grey clay ridges, eroded into gullies and biancane (white clay domes), stretch across a treeless terrain that looks almost lunar. This circular walk starts in the village of Asciano (30 minutes from Siena by car or bus), heading south through the crete landscape along farm tracks and white gravel roads (strade bianche). The route passes isolated farmhouses, fields of wheat and sunflowers, and the striking Abbazia di Monte Oliveto Maggiore — a 14th-century Benedictine monastery set in a cypress grove, famous for Luca Signorelli and Sodoma's fresco cycle depicting the life of Saint Benedict. The abbey has a pharmacy selling herbal products made by the monks. The landscape changes dramatically with the seasons — green and wildflower-dotted in spring, golden and parched in summer, misty and atmospheric in autumn. This walk is best in April–May or September–October.
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