Tuscany (Italy)
Siena is a medieval hill city built around the shell-shaped Piazza del Campo, with a striped cathedral, a town hall and a 102 metre tower you can climb, and it sits at the head of southern Tuscany's hill towns and wine country.
This guide covers the essentials plainly: the cathedral complex and its inlaid floor, the Palazzo Pubblico and Torre del Mangia, the free Campo, Santa Maria della Scala, San Gimignano and its frescoed Collegiata, walled Monteriggioni, Montepulciano and its Vino Nobile cellars, Montalcino and the Temple of Brunello, the Val d'Orcia, Pienza and a small-group day through Chianti, plus a food tour, a cooking class, a truffle hunt, an underground wine tasting and a guided walk. It also matches you to eight hotels, from a budget room near the Campo to a five-star monastery, with six guides on three days, eating and drinking, the best time to visit, day trips, first-timer planning and where to stay.
Siena Cathedral and the Piccolomini Library
Siena's black-and-white striped cathedral is one of Italy's great Gothic churches, with a carved marble pulpit, a floor of 56 inlaid panels and the painted Piccolomini Library. The floor is uncovered only for part of the year, so check the schedule before you go.
Palazzo Pubblico and Torre del Mangia
The town hall on Piazza del Campo holds the Civic Museum and its famous frescoes of good and bad government, and beside it rises the 102 metre Torre del Mangia, which you climb on foot for the best view in Siena.
San Gimignano and the Collegiata
The medieval town of towers is Tuscany's most photographed skyline, and its Collegiata church is covered in fourteenth-century frescoes. Winter hours are shorter, so check before you travel.
Piazza del Campo
Siena's shell-shaped main square is free to enter, slopes gently toward the Palazzo Pubblico and is the best place in the city to sit, watch and take it all in. It is also the track for the Palio, run twice a year.
Hand-picked: every experience here has strong traveler reviews and a verified booking link.
Siena's black-and-white striped cathedral is one of Italy's great Gothic churches, with a carved marble pulpit, a floor of 56 inlaid panels and the painted Piccolomini Library. The floor is uncovered only for part of the year, so check the schedule before you go.
The town hall on Piazza del Campo holds the Civic Museum and its famous frescoes of good and bad government, and beside it rises the 102 metre Torre del Mangia, which you climb on foot for the best view in Siena.
FreeSiena's shell-shaped main square is free to enter, slopes gently toward the Palazzo Pubblico and is the best place in the city to sit, watch and take it all in. It is also the track for the Palio, run twice a year.
Across from the cathedral stands one of the oldest hospitals in Europe, now a museum complex with frescoed halls, underground passages and the original statues from the Fonte Gaia. In winter it closes on Tuesdays.
The medieval town of towers is Tuscany's most photographed skyline, and its Collegiata church is covered in fourteenth-century frescoes. Winter hours are shorter, so check before you travel.
FreeA hilltop town of Renaissance palaces and deep wine cellars, home to Vino Nobile and a Piazza Grande with a tower you can climb. It is free to wander, and the views reach across two valleys.
A hill town known for Brunello, with an immersive museum of the wine inside a former convent. The temple can have limited opening days outside peak season, and the town holds a white truffle fair in November in most years.
FreeRolling hills, cypress-lined roads and hilltop hamlets make the Val d'Orcia the picture most people have of Tuscany. It is a free landscape to drive, with thermal baths at Bagno Vignoni and a fortress at Radicofani.
FreePope Pius II rebuilt his birthplace as an ideal Renaissance town in the 1400s, and little has changed since. Pienza is free to wander, with a hanging garden view over the Val d'Orcia and a famous pecorino cheese.
A small-group day through the Chianti hills from Siena, with castle visits, a Tuscan lunch and a wine tasting. It is the simplest way to see the vineyards without a designated driver.
A guided walk through Siena's food shops and lanes that ends in a sit-down Tuscan meal, a relaxed way to taste pici, cured meats, pecorino, panforte and local wine in a single afternoon.
A walk in the woods with a truffle hunter and a trained dog, followed by a tasting of local products. It is one of the most memorable half days in the Sienese countryside and rated 5.0 by past guests.
Hotels we would book ourselves, from splurges to good-value bases.
$$$$Banchi di Sopra, Siena city centre
A five-star hotel on Siena's main shopping street, a few minutes on foot from Piazza del Campo and the cathedral, with a frescoed ballroom, a courtyard bar, afternoon tea and rooms with Duomo views.
Check rates →Pian dei Mantellini, Siena historic centre
A family-run heritage hotel in a restored palace since 1924, with a walled panoramic garden, a veranda breakfast of local products and a walk of about six minutes to Piazza del Campo.
Check rates →Siena historic centre
A four-class hotel of about one hundred rooms in Siena's historic centre, with a rooftop terrace, an on-site restaurant, free self parking and a pet-friendly policy that is rare in the city.
Check rates →Piazza della Cisterna, San Gimignano
A three-class hotel on San Gimignano's main square, with valley-view balconies, a regional restaurant called Le Terrazze and a one-minute walk to the Collegiata. The old town is mostly car-free, so park outside.
Check rates →Via Montanini, Siena city centre
A simple two-class hotel on Via Montanini, five minutes on foot from Piazza del Campo and six from the cathedral, with single to quadruple rooms, a 24-hour front desk and a low price for the old town.
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$$$$Strada di Certosa, just outside Siena's walls
A five-class hotel in a former Carthusian monastery founded in 1314, set in gardens just outside Siena's walls, with a pool, a cloister restaurant, free parking and a free breakfast buffet.
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$$Via Enea Silvio Piccolomini, near Porta Romana, Siena
A three-class family-style hotel with a garden, a rooftop terrace, free breakfast and countryside views, by the Porta Romana gate and about a fourteen-minute walk from Piazza del Campo.
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$$$Strada di Scacciapensieri, north of Siena
A four-class boutique hotel in a hilltop villa just north of Siena, with a garden, a rooftop terrace, a seasonal pool, a restaurant and a free breakfast. A car is recommended.
Check rates →A practical first-timer guide to Siena, San Gimignano, Montepulciano, Montalcino, the Val d'Orcia and Chianti: what to book ahead, how to get around, how many days and what to expect through the year.
Where to stay for Siena and southern Tuscany: the historic centre near Piazza del Campo or a night inside San Gimignano, matched to eight hotels from budget to five-star.
A three-day plan for Siena and southern Tuscany: the cathedral, Piazza del Campo and Torre del Mangia on day one, a hill-town and Chianti day, and a Val d'Orcia day with wine.
What to eat and drink in Siena and southern Tuscany: pici and Cinta Senese, pecorino from Pienza, Sienese sweets, Chianti Classico, Brunello and Vino Nobile, plus food tours, cooking classes and truffle hunts.
When to visit Siena and southern Tuscany: spring greens, summer heat and the Palio, autumn harvest and truffles, and quiet winters, with notes on crowds, hours and what each season does to the countryside.
The best day trips from Siena: San Gimignano and Monteriggioni, Chianti by guided tour, and a Val d'Orcia day with Pienza, Montalcino and Montepulciano, with distances, transport and combination tips.
