Most people who visit Tuscany spend their days in Florence and never venture further south. That is a real shame. South of Florence, the landscape opens up into rolling clay hills, medieval hill towns, and ancient vineyards that look exactly like a Renaissance painting come to life. Siena, Pienza, Montepulciano, and the Val d’Orcia valley are among the most beautiful places in all of Italy — and far fewer tourists know about them than you might think. This guide gives you a complete tuscany itinerary hidden gems that most visitors miss entirely.
This route takes you through the very best of southern Tuscany. You do not need a private guide or a large budget. You need a hire car, a few nights in the right places, and an appetite — because the food in this part of Italy is extraordinary. If you are planning a broader trip, start with The Ultimate Italy Travel Guide before diving into this itinerary.
Why Southern Tuscany Is Worth the Journey
The area south of Florence — known broadly as the Crete Senesi and the Val d’Orcia — is a UNESCO World Heritage landscape. The hills are made of pale clay that turns gold in the evening light. Rows of cypress trees line the ridge roads. Vineyards and olive groves stretch in every direction. And at the centre of it all sits Siena, one of the great medieval cities of Europe.
The towns in this region are compact and walkable. Crowds are thinner than in Florence or the Amalfi Coast. Hotels cost less. The restaurants serve local food that is rooted in centuries of tradition. Wine from Montalcino and Montepulciano is world-class. In short, this is Tuscany at its most honest.
If you are looking for more ways to explore the region off the beaten path, take a look at our guide to hidden Tuscany villages for smaller stops you can add to this itinerary.
Getting There and Getting Around
The closest major airports are Florence (FLR) and Rome Fiumicino (FCO). Florence is closer but smaller. Rome gives you more flight options, especially from outside Europe. From Rome, Siena is roughly two and a half hours by road.
You need a hire car for this trip. The Val d’Orcia towns are connected by winding country roads, and public transport between them is infrequent and slow. Driving here is genuinely enjoyable — the roads are quiet, the scenery is spectacular, and parking in the smaller towns is straightforward. Just check ZTL (restricted traffic zone) signs before driving into any town centre. Most historic centres are restricted to residents.
Petrol is expensive in Italy. Factor that into your budget before you go. For a broader look at what a trip to Italy costs, our Italy travel budget guide breaks everything down clearly.
Day One and Two: Siena
Start in Siena. Give it two full days because it deserves them. Siena is one of the best-preserved medieval cities in Europe, and it is entirely car-free in the centre. The Piazza del Campo is one of the great public spaces on earth — a fan-shaped brick square that slopes gently down to the Palazzo Pubblico. Sit here with a coffee in the morning and you will understand immediately why people fall in love with this city.
The Siena Duomo is extraordinary. It is smaller than Florence’s cathedral but far more ornate — black-and-white marble striped inside and out, with a floor made of 56 inlaid marble panels covering scenes from the Old Testament. The Libreria Piccolomini inside the cathedral is one of the best-preserved Renaissance interiors in Italy, with bright frescoes covering every surface.
Climb the Torre del Mangia, the tall tower at the edge of the Piazza del Campo. The views over the rooftops and the surrounding hills are worth every step of the 400-stair climb. Book timed entry in advance, especially in summer.
Where to Eat in Siena
Siena has its own food traditions quite distinct from Florence. Look for pici — thick, hand-rolled pasta that looks like fat spaghetti — served with a wild boar ragu or a simple garlic-and-oil sauce. Ribollita is a hearty bread-and-vegetable soup that originated in Tuscany and is done particularly well here. For something sweet, try ricciarelli — soft almond biscuits dusted with icing sugar — or the dense spiced fruit cake called panforte, which has been made in Siena since the Middle Ages.
The Mercato Centrale on Piazza del Mercato sells local produce every morning. It is a good place to pick up cheese, salumi, and bread for a picnic in the hills.
Day Three: The Crete Senesi
Drive south from Siena through the Crete Senesi — a landscape of pale clay hills that looks unlike anywhere else in Tuscany. The colour of the soil shifts from cream to ochre depending on the light and the season. In spring the hills are dotted with poppies. In summer they turn a bleached golden colour. In autumn they go rust and amber.
Stop at Asciano, a small medieval town with a good Etruscan museum and a beautiful Romanesque church. Then continue to the Abbazia di Monte Oliveto Maggiore — a Benedictine monastery hidden in a forest of cypress trees. The frescoes in the great cloister, painted by Luca Signorelli and Il Sodoma in the early 1500s, depict the life of Saint Benedict across 36 panels. Entry is free. The monks still live and work here and sell their own honey, soap, and wine.
Have lunch in Buonconvento, a small walled town with a good local trattoria and a museum dedicated to Sienese art. Then drive south toward Montalcino in the afternoon.
Day Four: Montalcino and Brunello Wine
Montalcino is a hill town famous for one thing above all others: Brunello di Montalcino, one of Italy’s great red wines. The town sits high above the Val d’Orcia with views in every direction. The fortress at the top of the town houses a wine bar where you can taste Brunello, Rosso di Montalcino, and other local bottles without booking in advance. It is one of the best-value wine experiences in all of Tuscany.
Walk the medieval walls and explore the small streets. The town is genuinely medieval and has not been overdeveloped for tourism. There is a good food market on Friday mornings. In the afternoon, drive down to the valley floor to visit the Abbey of Sant’Antimo. This Romanesque abbey dates to the 9th century and sits alone in a valley of olive groves and vineyards. The monks chant Gregorian plainsong several times a day and visitors are welcome to attend. It is one of the quietest, most beautiful places in Tuscany.
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Day Five: Pienza — The Perfect Renaissance Town
Pienza is one of the most satisfying places in all of Italy. In the 1460s, Pope Pius II decided to rebuild his birthplace as a model Renaissance town. He hired the architect Bernardo Rossellino, who designed a central piazza flanked by a cathedral, a papal palace, a town hall, and a bishop’s palace — all in perfect proportion. The result is the purest example of Renaissance urban planning in Italy. The entire town centre is a UNESCO World Heritage Site.
The cathedral is beautiful and small. The papal palace beside it contains a fine collection of Flemish tapestries and painted wood panels. The views from the garden behind the palace look directly out over the Val d’Orcia — the clay hills, the valley floor, and Monte Amiata in the distance. It is one of the finest views in Tuscany.
Pienza is also famous for its sheep’s milk cheese, pecorino di Pienza. The main street is lined with small food shops selling the cheese at every stage of ageing — fresh, semi-aged, aged, and aged in walnut leaves or ash. Buy some for a picnic and eat it on a bench looking out over the valley.
The Road Between Pienza and Montepulciano
The SP146 road between Pienza and Montepulciano is one of the most photographed roads in Italy. The long straight avenue lined with cypress trees at the foot of the hill — the Cipressi di San Quirico d’Orcia — is the image that appears on a thousand Italy travel posters. Drive it slowly. Stop and walk to the edge of the road. Take your time. The whole valley looks like a painting from every angle.
Day Six: Montepulciano and Bagno Vignoni
Montepulciano is a larger hill town built along a single steep ridge. The main street climbs from the lower gate to the top of the hill, passing Renaissance palaces, wine shops, and local food stores on the way. The Piazza Grande at the top has a cathedral, a well, and views over the surrounding countryside.
The town produces Vino Nobile di Montepulciano, another of Tuscany’s finest red wines. Most of the producers have enoteche (wine shops) on the main street where you can taste before you buy. The cantina at the Contucci winery is particularly atmospheric — it is built into the cellars beneath the town.
Spend the afternoon driving through the Val d’Orcia itself. Stop at Bagno Vignoni — a tiny village built around a large thermal pool in the main piazza. The pool itself is historic and not for swimming, but several spa hotels nearby offer access to the thermal waters. San Quirico d’Orcia is worth a short stop for its Romanesque collegiate church, which has one of the finest carved doorways in Tuscany.
Day Seven: The Chianti Wine Road North
On the final day, take the slow road north through the Chianti wine country. The Chiantigiana road (SR222) runs through the heart of the Chianti Classico wine region between Siena and Florence. It is one of the most scenic drives in Italy — winding through oak forests, vineyards, and small villages perched on hilltops.
Stop in Greve in Chianti, the main market town of the region, for lunch. The large triangular piazza has a weekly market and several good restaurants. Call into one of the wine producers on the road — many offer walk-in tastings. The Castello di Brolio, a working castle that has been owned by the Ricasoli family for centuries, gives tours of the cellars and has extraordinary views over the wine country.
If you want to extend your time in the region, our 7-day Tuscany road trip itinerary gives you an alternative route that takes in the northern hills and coast.
Where to Stay in the Val d’Orcia
Staying in an agriturismo is the best way to experience this part of Tuscany. These are working farms that let rooms, usually with a pool and breakfast included. The quality is high and the prices are far lower than equivalent hotels in the towns. Look for options near Montalcino, in the hills above Pienza, or on the road between Montepulciano and Chianciano Terme.
The hill towns themselves have a good range of hotels. Siena has the largest choice, from budget B&Bs in the old city to four-star hotels just outside the walls. Montepulciano has several small hotels in historic buildings on the main street. Pienza has a handful of boutique hotels and guesthouses in the old town.
Book accommodation well in advance if you are visiting between May and September. The Val d’Orcia is popular with Italian and European visitors, and the best places fill up quickly. For logistics information that applies across Tuscany, the Florence travel guide has useful advice on transport, tipping, and planning.
Best Time to Visit Southern Tuscany
The best months are May, June, September, and October. Spring brings wildflowers to the hills and the weather is warm without being hot. Early summer has long days and good light for photography. September brings the grape harvest — one of the most atmospheric times to be in wine country. October has spectacular autumn colour in the woods around Chianti.
July and August are the hottest months. The hills can reach 35 degrees Celsius or more. Siena’s famous Palio horse race takes place twice in summer — on 2 July and 16 August — and draws enormous crowds. If you want to see the Palio, book accommodation a year in advance. If you do not, consider avoiding Siena on those dates.
Winter is quiet and cold but has its own appeal. The towns are almost empty of tourists, accommodation is cheap, and the landscape looks austere and beautiful under grey skies. Truffle season runs from late autumn through winter, and white truffles from nearby San Miniato are served in local restaurants.
Practical Tips for This Tuscany Itinerary
- Book hire car early. Car hire in Tuscany is competitive. Book through a comparison site at least two weeks in advance and check for deals at smaller regional airports.
- Carry cash. Many small restaurants, farm shops, and rural producers in Tuscany do not accept cards. An ATM in every main town keeps you covered.
- Check ZTL zones. Restricted traffic zones in historic town centres carry automatic fines. Check Google Maps or your GPS before driving into any old town.
- Book wine tastings. Many of the best Brunello and Vino Nobile producers require advance booking for cellar tours. Do this before you leave home.
- Start early. Parking in the main towns fills by mid-morning in summer. Leave your accommodation early, park, then walk back into town for breakfast.
- Learn a few words of Italian. Outside the main tourist spots, English is less widely spoken. Even basic phrases are appreciated and make interactions much warmer.
Frequently Asked Questions
How many days do you need for the Val d’Orcia?
Allow a minimum of three to four days to see the main highlights — Pienza, Montalcino, Montepulciano, and the valley itself. A full week lets you add Siena at the start and the Chianti road at the end, which gives a much richer experience of the whole region.
Is Siena worth visiting if you have already been to Florence?
Absolutely. Siena and Florence are rivals in Italian culture but completely different in character. Siena is smaller, more compact, more medieval, and feels less commercial than Florence. The Duomo and the Piazza del Campo alone justify the visit, and the local food traditions are distinct and excellent.
What is the Val d’Orcia known for?
The Val d’Orcia is a UNESCO World Heritage cultural landscape in southern Tuscany, famous for its rolling clay hills, cypress-lined roads, medieval hill towns, and exceptional wines including Brunello di Montalcino and Vino Nobile di Montepulciano. It is considered one of the most beautiful landscapes in Italy.
Where is the best place to try Brunello di Montalcino?
The wine bar inside Montalcino’s fortress is the easiest option — no booking needed and a wide selection available by the glass. For a deeper experience, producers such as Biondi-Santi, Banfi, or Casanova di Neri offer cellar tours with advance booking.
You Might Also Enjoy
- Hidden Tuscany Villages Off the Beaten Path
- 7-Day Tuscany Road Trip Itinerary
- The Ultimate Italy Travel Guide
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