✦ Top pick
Siena is the best all-rounder for its Gothic grandeur and easy access; choose Lucca for a relaxed car-free day, San Gimignano for postcard towers, or Fiesole if you only have a half day.
Florence is the front door to Tuscany, and some of the region's best days out are the small towns within an hour or two of the city. A quick regional train or a countryside bus drops you into walled medieval cities, wine villages ringed by vineyards, and hilltop stone towns where the pace slows to an espresso and a passeggiata.
This list ranks eight towns that reward the trip, balancing what's easy to reach by public transport with places worth renting a car for. Each entry tells you how far it is, how to get there, what to see and eat, and who it suits best, so you can match a town to the kind of day you want.
Use the travel times as your filter: Fiesole and Lucca are effortless by bus and train, Siena and San Gimignano are classic full-day trips (and easy on a guided tour), while Montepulciano and Pienza reward those willing to drive deeper into the Val d'Orcia.
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1tours from $99.35Siena Google
Siena is the heavyweight of Tuscan day trips: a perfectly preserved medieval city built around the Piazza del Campo, the shell-shaped square where the Palio horse race thunders each July and August. Climb the Torre del Mangia for rooftop views, step inside the striped marble Duomo with its inlaid marble floor, and wander lanes that have barely changed in 700 years. It feels grander and more complete than any other town on this list, yet stays walkable in a single day. Fuel up on pici pasta and panforte, the dense honeyed cake Siena has made since the Middle Ages.
- Piazza del Campo and the Torre del Mangia climb
- Siena's black-and-white striped Duomo and marble floors
- Pici cacio e pepe and a slice of panforte
Best for first-timers who want the full Tuscan-city experience
Getting there About 1h15 by direct Autolinee Toscane bus (line 131R) or roughly 1h30 by regional train via Empoli; around 1h by car
2tours from $91.80San Gimignano Google
Known as the medieval Manhattan, San Gimignano bristles with 14 surviving stone towers that noble families raced to build ever taller. It's small enough to see in a few hours, but the views over the vineyards from the top of the town are among the best in Tuscany. Sip the local Vernaccia di San Gimignano, the region's crisp white wine, and try the world-champion gelato at Gelateria Dondoli on Piazza della Cisterna. Come early or stay for the evening, as day-trip coaches pack the lanes at midday.
- The skyline of medieval towers and Torre Grossa
- Vernaccia di San Gimignano white wine
- Award-winning gelato at Gelateria Dondoli
Best for photographers and a classic half-day stop
Getting there No direct train; about 1h30 by bus via Poggibonsi, or an easy stop on a guided Tuscany tour; roughly 1h by car
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3Lucca Google
Lucca is the most relaxed town near Florence and the easiest to reach car-free, wrapped in intact Renaissance walls so wide you can cycle or stroll the full circuit on top. Inside, it's a maze of quiet piazzas, medieval churches, and the oval Piazza dell'Anfiteatro, built on the footprint of a Roman amphitheater. Rent a bike, climb the tree-topped Torre Guinigi, and catch a Puccini concert in the composer's hometown. It pairs neatly with Pisa, 30 minutes further down the same line.
- Cycling the Renaissance city walls
- Piazza dell'Anfiteatro and Torre Guinigi
- A Puccini concert or the San Michele church
Best for a slow, car-free day and cyclists
Getting there Direct regional train, about 1h20 to 1h30, hourly, around €8 each way
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4Fiesole Google
If you only have a half day, Fiesole is the easiest escape: a hilltop town a short city bus ride above Florence with sweeping views back over the Duomo and the Arno valley. It predates Florence as an Etruscan settlement, and you can walk through a well-preserved Roman theater and archaeological area still used for summer concerts. Climb to the San Francesco monastery for the best panorama, then linger over lunch on the main square. It's the go-to for a sunset aperitivo away from the crowds.
- Roman theater and Etruscan archaeological area
- Panoramic view from Convento di San Francesco
- Sunset aperitivo over the Florence skyline
Best for a half day and travelers without a car
Getting there About 25 to 30 minutes on ATAF city bus line 7 from central Florence
5tours from $63.91Greve in Chianti Google
Greve is the unofficial capital of the Chianti Classico wine country, a friendly market town built around the funnel-shaped Piazza Matteotti lined with arcades and wine shops. Base yourself here to taste the black-rooster Chianti Classico, visit the historic Antica Macelleria Falorni butcher for wild boar salami, and drive the vineyard roads to villages like Panzano and Montefioralle. The town itself is unpretentious and lively, especially during the September wine festival. This is the closest true Tuscan wine escape from Florence.
- Chianti Classico tastings around Piazza Matteotti
- Cured meats at Antica Macelleria Falorni
- The tiny hamlet of Montefioralle nearby
Best for wine lovers and a short countryside escape
Getting there About 1h by SITA/Autolinee Toscane bus, or roughly 45 minutes by car; easiest with a Chianti wine tour
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6Arezzo Google
Arezzo is an underrated Renaissance city that most day-trippers skip, which is exactly its appeal. The sloping Piazza Grande, framed by medieval and Vasari-designed buildings, hosts the twice-yearly Giostra del Saracino joust and a famous monthly antiques market, one of Italy's largest. Don't miss Piero della Francesca's luminous fresco cycle in the Basilica di San Francesco, a Renaissance masterpiece you can often see without a queue. Fans of cinema will recognize the streets from Roberto Benigni's Life Is Beautiful.
- Piero della Francesca frescoes in San Francesco
- Piazza Grande and the monthly antiques fair
- Life Is Beautiful film locations
Best for art lovers who want fewer crowds
Getting there Direct regional train, about 1h, frequent, around €9 to €12 each way
7Cortona Google
Perched high above the Val di Chiana, Cortona is the hill town made famous by Under the Tuscan Sun, all steep stone lanes, Etruscan walls, and long views toward Lake Trasimeno. Climb to the Fortezza del Girifalco for the widest panorama, see Fra Angelico's Annunciation in the Diocesan Museum, and settle into a piazza cafe as the light turns gold. It takes effort to reach and to climb, but rewards you with an authentic, less-trampled hilltop atmosphere. Stay overnight to have the town to yourself after the buses leave.
- Views from Fortezza del Girifalco
- Fra Angelico's Annunciation in the Museo Diocesano
- Etruscan walls and steep medieval lanes
Best for a scenic overnight and film-location fans
Getting there Train to Camucia-Cortona (about 1h15 to 1h40), then a short shuttle bus up the hill; easier by car
8Montepulciano Google
Montepulciano is a dramatic ridge-top town famous for Vino Nobile di Montepulciano, a bold red you can taste in atmospheric cellars carved deep beneath the main street. Walk up the Corso to the Renaissance Piazza Grande, then descend into historic cantinas like Contucci for a tasting straight from the barrel. The surrounding Val d'Orcia is the postcard Tuscany of cypress rows and golden hills, and the elegant Renaissance town of Pienza is just 20 minutes away. This is a trip that pairs best with a rental car and an overnight.
- Vino Nobile tastings in underground cellars
- Piazza Grande and the climb up the Corso
- A side trip to nearby Pienza and its pecorino cheese
Best for wine and scenery seekers with a car
Getting there Best by car, about 1h45 to 2h; by public transport, train to Montepulciano station then a connecting bus (allow 2h30+)
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✦ Good to know
Before you go
Getting aroundTrains from Firenze Santa Maria Novella are the simplest option for Lucca, Arezzo, and Pisa. For Siena, Chianti, and San Gimignano the Autolinee Toscane buses are often faster and more direct than the train, and deeper Val d'Orcia towns like Montepulciano and Pienza really need a car.
Book tickets smartBuy regional train tickets at the station machine or the app and validate before boarding; they are cheap and don't need advance booking. Reserve Siena's Duomo and Uffizi-style sights ahead only in peak summer.
When to goApril to June and September to October offer the best weather and lighter crowds. Avoid arriving in San Gimignano or Siena at midday in July and August, when coach tours peak; go early or stay into the evening.
Consider a tour for the far townsIf you don't want to drive, a guided day trip is the easiest way to combine Siena, San Gimignano, and a Chianti winery in one day, since linking them by public transport is slow.
Whether you want the Gothic grandeur of Siena, a car-free ramble around Lucca's walls, or a slow afternoon of Chianti in Greve, the towns around Florence turn one great city into a whole region worth exploring. Pick one or two that match your travel style and pace, check the train and bus times, and build a day (or an overnight) that gets you into the real Tuscany just beyond the Duomo.
Frequently asked questions
Which small town near Florence is best for a day trip without a car?
Lucca is the easiest: a direct regional train runs hourly and takes about 1h20 to 1h30. Siena and Arezzo are also reachable by direct bus or train in around an hour, and Fiesole is just a 25-minute city bus ride.
How do you get from Florence to Siena?
The fastest way is the direct Autolinee Toscane bus (line 131R) from Florence, which takes about 1h15. The regional train takes slightly longer, around 1h30, because it usually requires a change at Empoli.
What is the closest town to Florence for a half-day trip?
Fiesole, in the hills just above the city, is the closest at about 8 km. City bus line 7 gets you there in roughly 25 to 30 minutes, and you get Roman ruins and panoramic views over Florence.
Which town near Florence is best for wine?
Greve in Chianti is the most accessible wine base, at the heart of the Chianti Classico region about 45 minutes away. For a bolder red and dramatic scenery, Montepulciano and its Vino Nobile cellars are worth the longer drive south.
Can you visit Siena and San Gimignano in one day?
Yes, but it's difficult by public transport since you'd change buses in Poggibonsi. A guided day trip from Florence is the most efficient way to combine both, often with a Chianti winery lunch included.
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