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A shell shaped brick square sloping toward the Gothic town hall and its tall slender tower

Piazza del Campo and the Torre del Mangia, Siena · Photo: Perituss · CC0

Tuscany

Toscana

Siena, San Gimignano, Chianti, the Val d'Orcia, Lucca and Pisa: how to see the Tuscan hill towns and wine country, by car or by bus and train, with tickets, bases and sample routes.

Verified October 202614 min readTuscany
TUSCANYTOSCANA
Best time
Late April–June and September–October (grape harvest in September)
Gateway
Florence; Pisa airport for the coast and Lucca
Time needed
5–7 days beyond Florence for the hill towns and countryside
Car?
Essential for Chianti and the Val d'Orcia; not needed for Siena, Lucca or Pisa
Siena Duomo
Marble floor uncovered until November 15, 2026; OPA SI Pass €16 (about $18)
Palio di Siena
July 2 and August 16, every year
Buses
Autolinee Toscane runs the regional network

Overview

Tuscany is the Italy of the postcards: cypress-lined lanes, stone hill towns, vineyards and olive groves. It is also a working region of about 3.6 million people, with industrial outskirts and summer crowds in the famous towns. Choose a base or two and move slowly.

Think of it in three parts. The cities (Siena, Lucca, Pisa, Arezzo) are easy by train and bus. The wine country (Chianti between Florence and Siena, Montalcino and Montepulciano farther south) and the Val d'Orcia landscape need a car or a tour. And the coast and Maremma to the west and south are for beaches, hot springs and fewer Americans. Florence has its own page.

Choosing a base

Most people do best with two bases rather than moving every night.

  • Without a car: Florence plus Siena or Lucca. Both have good bus and train links and plenty to see on foot.
  • With a car: a few car-free nights in Florence, then 3–5 nights in an agriturismo (working farm with rooms) in Chianti or the Val d'Orcia.
  • Short on time: Siena is the best single base, lovely after the day-trippers leave, with buses to San Gimignano, Montalcino and Montepulciano.

Insider tip

An agriturismo is often the best-value stay in Tuscany, and many serve dinner made from their own produce. In summer, look for one with a pool; inland Tuscany gets very hot in July and August. Most require a minimum stay in high season. See where to stay.

Medieval stone towers rising above the rooftops of a hill town in golden evening light
The towers of San Gimignano at sunset, TuscanyPhoto: Julian Lupyan · CC0

Siena

Siena, about 45 miles (75 km) south of Florence, was Florence's great medieval rival, and it still looks it: a Gothic brick city on three ridges, built around the shell-shaped Piazza del Campo. Day-trippers fill it from 10 a.m. to 5 p.m. Stay a night and you see the Campo empty in the early morning and full of Sienese at night.

The Duomo complex

Siena's black-and-white striped cathedral has a pulpit by Nicola Pisano, Pinturicchio's vivid frescoes in the Piccolomini Library, and a floor of inlaid marble scenes made over two centuries, usually kept covered and shown only part of the year. In 2026 it is uncovered from June 27 to July 31 and from August 18 to November 15, so if you are visiting in the next few weeks, you will see it.

During the uncovering, prices from the Opera del Duomo are:

TicketIncludesPrice (2026 uncovering)
Cathedral onlyCathedral with the floor visible€10 (about $11)
OPA SI PassCathedral, Piccolomini Library, Museo dell'Opera, the Facciatone panorama, crypt, Baptistery; valid 3 consecutive days€16 (about $18)
Porta del CieloThe OPA SI Pass plus a guided walk on the cathedral roof€20 (about $22)

Book at operaduomo.siena.it. Prices drop when the floor is covered. Porta del Cielo rooftop visits run in small timed groups, so reserve those ahead. Climb the Facciatone, the unfinished wall of a vast new cathedral abandoned after the Black Death, for the best view of the city.

Piazza del Campo and the Palazzo Pubblico

The town hall on the Campo houses the Museo Civico, with Ambrogio Lorenzetti's fresco cycle on good and bad government, painted in the 1330s and still pointed. The Torre del Mangia beside it is about 400 steps; visits are in small timed groups and the tower can close in bad weather. Santa Maria della Scala, a medieval hospital across from the cathedral, is now a museum with remarkable frescoes of hospital life.

The Palio

The Palio is a bareback horse race around the Campo, run every year on July 2 and August 16. Ten of the city's seventeen contrade (neighborhoods with their own colors, churches and fierce loyalties) compete each time. The race lasts about 90 seconds; the pageantry, trial runs and celebrations fill several days. Standing in the center of the Campo is free but packed and hot, with no way out for hours. Seats on the stands and balconies are sold privately and cost a lot. See festivals.

Different from home

The Palio is the Sienese's own event, and it matters intensely to them. Treat it as a party or cheer the wrong horse in the wrong street and you'll get dirty looks. Follow your neighbors' lead, and keep children close in the Campo crowd.

Getting to Siena

From Florence, the bus is usually better than the train. Autolinee Toscane's express buses leave from the bus station beside Santa Maria Novella and drop you in the center at Piazza Gramsci, in about 1 hr 15 min. The train takes about 1 hr 30 min, sometimes with a change at Empoli, and Siena's station is at the bottom of the hill; a series of escalators and city buses bring you up into town. Both cost under €10 (about $11) one way; check current fares on the operator's site. Siena's center is a ZTL, like Florence's.

San Gimignano, Monteriggioni and Volterra

San Gimignano is the "medieval Manhattan": a walled hill town that once had dozens of family towers and still has more than a dozen. It is beautiful and, in the middle of the day, overwhelmed. Arrive before 10 a.m. or after 5 p.m., or better, stay a night. Climb the Torre Grosa in the town hall for the view, try the local white wine, Vernaccia di San Gimignano, and look for the gelato shops on Piazza della Cisterna. By public transport, take a train or bus to Poggibonsi and a local bus up the hill (about 25 minutes).

Monteriggioni, a tiny walled ring just north of Siena, is a 30-minute stop on the Siena–Florence drive. Volterra, on a high bluff to the west, has Etruscan gates, a Roman theater, alabaster workshops and the excellent Guarnacci Etruscan museum. It is hard to reach without a car.

Chianti

Chianti is the hilly wine country between Florence and Siena. The Chianti Classico zone, marked by the black rooster (gallo nero) on the bottle's neck, centers on the villages of Greve, Panzano, Castellina, Radda and Gaiole. The scenic road through it is the SR222, the Chiantigiana, which runs from Florence to Siena in about 1 hr 30 min without stops; plan a full day with stops.

Greve in Chianti

Village · 1–2 hr

A triangular arcaded piazza, wine shops and the Antica Macelleria Falorni, a butcher selling cured meats from local pigs. Easiest Chianti village by bus from Florence (about an hour).

Panzano

Village · 1 hr

Home of Dario Cecchini's butcher shop and restaurants, famous for meat and theater. Book meals well ahead.

Castellina, Radda and Gaiole

Villages · half day

Smaller hill villages in the heart of the zone, surrounded by estates. Radda is the prettiest; Castellina has a walled, covered medieval street.

Castello di Brolio

Estate near Gaiole · 2 hr

The Ricasoli family castle, where the modern Chianti blend was defined in the 1800s. Garden, chapel, ramparts and a tasting room.

Antinori nel Chianti Classico

Bargino · 2 hr

A striking modern winery built into a hillside, 30 minutes from Florence. Tours and tastings by reservation.

Book winery visits ahead, even small family estates; many are working farms with no one free to show you around unannounced. Tours with a tasting are priced per person and range from modest at small producers to restaurant prices at famous estates with lunch. See wine.

Watch out

Italy's blood-alcohol limit is 0.05%, lower than the 0.08% in most US states, and it is zero for drivers who have held a license for less than three years. Police run checkpoints on Chianti roads, especially on weekends. If you plan to taste seriously, book a driver or a small-group tour from Florence or Siena. See driving.

Neat rows of grapevines on a gentle slope leading up to a stone winery building and trees
A vineyard and winery in Gaiole in Chianti, TuscanyPhoto: Adbar · CC BY-SA 3.0
Thick brick ramparts of Lucca's city walls with trees growing along the top
The Renaissance city walls of LuccaPhoto: Notafly · CC BY-SA 4.0

The Val d'Orcia, Montalcino and Montepulciano

South of Siena, the Val d'Orcia is the landscape on the calendars: bare rolling hills, lines of cypresses, lone farmhouses. It is a UNESCO World Heritage Site, and it is best seen at dawn or in late afternoon light, in May for green fields or October for plowed earth and the wine harvest's end. You need a car or a guided tour; buses exist but are infrequent.

Pienza

Town · 2 hr

A Renaissance "ideal town" laid out by Pope Pius II in the 1460s. Small, elegant, with a walk along the walls overlooking the valley. Known for pecorino (sheep's cheese).

Montalcino

Town · 2–3 hr

The hilltop home of Brunello di Montalcino, one of Italy's greatest red wines. Wine bars and shops line the streets; the fortress has a tasting room.

Montepulciano

Town · 3 hr

A long, steep town of Renaissance palaces, with Vino Nobile cellars dug deep into the hill. Cantina de' Ricci's vaulted underground cellar is spectacular.

Bagno Vignoni

Hamlet · 1 hr

Its main square is a steaming thermal pool. You can't bathe in it, but nearby spa hotels have pools, and the free hot springs at Bagni San Filippo are 20 minutes south.

San Quirico and the Vitaleta chapel

Photo stops · 1 hr

San Quirico d'Orcia has formal gardens and a fine church. The little Vitaleta chapel and its cypresses, between San Quirico and Pienza, are the classic photo.

Distances are small (Montalcino to Pienza is about 15 miles/25 km, Pienza to Montepulciano about 8 miles/13 km), but roads wind and you'll stop constantly. To the east are Cortona, of Under the Tuscan Sun fame, and Arezzo, with Piero della Francesca's Legend of the True Cross frescoes (timed booking), about an hour from Florence by train.

Lucca and Pisa

Lucca

Lucca is flat, elegant and ringed by Renaissance walls topped with a tree-lined promenade about 2.6 miles (4.2 km) around. Rent a bike for the walls, then see the oval Piazza dell'Anfiteatro (on the footprint of the Roman arena), the Guinigi Tower with oak trees on top, and San Michele. Puccini was born here, and there are Puccini concerts most evenings. Regional trains from Florence take about 1 hr 20 min.

Every year around the end of October and start of November, Lucca Comics & Games takes over the whole town, one of the largest comics festivals in the world. Hotels fill a year ahead; check the dates if you are traveling then.

Pisa and the Leaning Tower

Pisa's Piazza dei Miracoli (Field of Miracles) sets the cathedral, the round Baptistery, the Camposanto cemetery and the leaning bell tower on one lawn. Most visitors give it two hours, which is fine, though the old center along the Arno is pleasant and very local.

Climbing the tower takes about 30 minutes, 251 steps up a worn spiral. Rules from the Opera della Primaziale Pisana:

  • Book online at opapisa.it, up to 90 days ahead. Tickets are timed, and if you are late you lose your slot without a refund.
  • Children who will not have turned 8 by the end of the current year cannot climb. Under-18s must be with an adult, and staff may check ID.
  • Bags, including small purses, go into the cloakroom before the climb. Large suitcases are not allowed in the complex.
  • Any ticket includes free entry to the cathedral, which is not tied to a time slot.

Tower tickets have been around €20 (about $22); combination tickets for the Baptistery, Camposanto and museum are sold separately. Check the official price page before you buy. The Pisa San Rossore station is the closest to the tower; from Pisa Centrale it is about a 25-minute walk. Pisa's airport is linked to Pisa Centrale by the PisaMover shuttle in about 5 minutes, which makes Pisa an easy first or last stop.

Save money

If you are flying into or out of Pisa, see the tower on the way: leave your bags at the station or airport left-luggage, take the train to San Rossore, and you can be back within three hours. That saves a separate day trip.

The coast, Maremma and islands

The Tuscan coast is where Florentines go in summer. Viareggio and Forte dei Marmi have long rows of stabilimenti (beach clubs that rent loungers and umbrellas by the day). The Maremma in the south is wilder, with the Parco della Maremma's beaches, the tuff towns of Pitigliano and Sorano, and the free hot-spring cascades at Saturnia. Elba, Napoleon's first place of exile, is about an hour by ferry from Piombino; book car space well ahead for August. For the Cinque Terre, just over the border in Liguria, see Cinque Terre, and for beach basics, outdoors.

Getting around

Trains

Trenitalia regional trains link Florence with Pisa (about an hour), Lucca, Arezzo and Siena, at fixed fares you can buy on the day. Validate paper regional tickets in the platform machine before boarding. San Gimignano, Montalcino and Pienza have no station.

Buses: Autolinee Toscane and Tiemme

Since 2021, regional and city buses across Tuscany have been run by a single company, Autolinee Toscane (at), which took over the routes of older local operators. You'll still see older names in guidebooks and occasionally on stops, such as Tiemme around Siena, Arezzo and Grosseto and Busitalia around Florence; the routes now belong to the at network. Check timetables and fares at at-bus.it or in the at bus app.

  • Contactless: you can tap a bank card or phone on the reader when you board. On urban buses tap once. On intercity and express buses tap when you get on and when you get off; if you forget the second tap, you are charged the maximum fare to the end of the line.
  • Schedules thin out on Sundays and holidays, and some rural routes run mainly for schoolchildren. Check the return bus before you go.
  • Useful routes: Florence–Siena express, Florence–Greve, Siena–Montalcino, Siena–Montepulciano and Poggibonsi–San Gimignano.

Driving

For the countryside, a car makes all the difference. Rent from Florence or Pisa airport, not the city center, to avoid the ZTL. Every town, even small ones, has a ZTL with cameras: park in the signed lots outside the walls and walk in. Blue lines mean paid parking, white lines usually mean free, and yellow lines are for residents or permit holders. The speed limit on the autostrada is 130 km/h (81 mph); the toll-free Florence–Siena expressway is slower and has speed cameras. US drivers need an International Driving Permit along with their license. See driving in Italy.

Watch out

Siena, Lucca, San Gimignano and Montepulciano all catch rental cars in their ZTLs, as Florence does. If you see a round white sign with a red border and "ZTL" beneath it, do not drive past it unless your hotel has registered your plate.

Where to stay

Siena old town

City base · $$–$$$

Stay inside the walls so you can walk to the Campo at night. Look for hotels with parking outside the ZTL if you have a car.

Chianti agriturismo

Countryside · $$–$$$

Farm stays between Greve and Radda keep you within an hour of both Florence and Siena. Good for 3–5 nights.

Montepulciano or Pienza

Val d'Orcia base · $$

Small hotels and rooms in town, or farm stays just outside, put you in the middle of the valley at golden hour.

Lucca inside the walls

City base · $$

Calm, walkable, with good trains to Florence and Pisa. Easy without a car.

Castello di Ama

Gaiole in Chianti · $$$$

A wine estate with a handful of rooms and contemporary art installed among the vineyards.

Rosewood Castiglion del Bosco

Montalcino · $$$$

A restored medieval estate with its own Brunello winery and golf course. For a honeymoon or a big splurge.

Most Tuscan towns charge a tourist tax, typically a few euros per person per night, collected at checkout. Florence's is the highest in the region (see Florence).

Sample routes

Five days without a car

  1. Day 1

    Florence to Siena

    Morning express bus from Florence to Siena. Afternoon in the Duomo complex with the OPA SI Pass; climb the Facciatone. Aperitivo on the Campo.

  2. Day 2

    Siena

    Museo Civico and the Torre del Mangia early, Santa Maria della Scala, and the rest of the Duomo pass. Evening walk through the contrade.

  3. Day 3

    Montalcino or Montepulciano

    Bus from Siena to Montalcino for Brunello tastings in town (or to Montepulciano for its cellars). Check the return bus first.

  4. Day 4

    San Gimignano

    Bus via Poggibonsi. Arrive early, climb the Torre Grosa, lunch, and leave before the late-afternoon return buses fill. Continue to Florence or back to Siena.

  5. Day 5

    Lucca and Pisa

    Train from Florence to Lucca, bike the walls, then on to Pisa for an afternoon tower slot. Fly out of Pisa or return to Florence.

Seven days with a car

  1. Day 1

    Into Chianti

    Pick up the car at Florence airport. Drive the SR222 through Greve and Panzano to your agriturismo. Dinner at the farm.

  2. Day 2

    Chianti wineries

    A morning tasting at Castello di Brolio or another estate, lunch in Radda, an afternoon visit to Castellina.

  3. Day 3

    Siena

    Park outside the walls and spend the day in Siena. Back to the farm for dinner.

  4. Day 4

    San Gimignano and Volterra

    San Gimignano at opening, then the drive west to Volterra for the Etruscan museum and sunset from the walls.

  5. Day 5

    To the Val d'Orcia

    Drive south via Monteriggioni and Montalcino. Check into a farm stay near Pienza.

  6. Day 6

    Pienza, Bagno Vignoni and Montepulciano

    Dawn photos near San Quirico and the Vitaleta chapel, pecorino in Pienza, a soak at a spa or the springs at Bagni San Filippo, cellars in Montepulciano.

  7. Day 7

    Onward

    Continue to Umbria (Orvieto is about an hour from Montepulciano), or drive to Chiusi and take the train to Rome or Florence.

What trips people up

  • Trying to see Siena, San Gimignano and Chianti in one day from Florence. Tour buses do it; you'll see the inside of the bus. Pick one or two.
  • Afternoon closures. Shops and many wineries in small towns close from about 1 to 4 p.m. Plan lunch, not errands.
  • Heat. July and August highs inland often top 95°F (35°C). Do sights early, rest after lunch. See health.
  • Fake "Chianti" tours. Check that a tour actually visits wineries in the Chianti Classico zone and how many tastings are included.
  • Palio days. Book Siena rooms months ahead for July 2 and August 16, or avoid the city those days.

For more on timing, see when to go; for routes that combine Tuscany with Rome and Venice, see planning your trip.

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