The 10 best towns with a serious restaurant that eat well within 90 minutes of Florence
Ten towns: what each is best for, what a home costs, and the catch. A square meter runs from €1,000 in Poppi to €4,200 in Siena.
We've written about 6 of these 10. From the 1,000 towns picked by Peter Benei.
92 towns written about, 908 to go. Follow along, free: Subscribe on Substack
The country around Florence is built for eating. Vines and olives run up the slopes in bands, oak and chestnut close over the higher roads, and the towns sit on ridges of gray sandstone with terracotta roofs and cellars cut into the rock beneath them. Autumn brings porcini, new oil pressed cloudy and green, and white truffle from the sandy hills to the west. Winter is the season of bistecca alla fiorentina, ribollita thickened with black cabbage, and pici rolled by hand under the thumb.
Most visitors eat in Florence, and the good tables there are booked weeks out. The center between the Duomo and the Ponte Vecchio is dense with restaurants that know a diner will only ever come once, and the queue outside the tripe stalls at lunchtime tells you everything about the volume. There is genuine cooking in the city, but you pay for it in planning and in elbows.
The same hills, the same butchers and the same producers carry on past the ring road. Chianti Classico, the Casentino, the Valdarno and the Sienese Crete are all within an easy drive, and the kitchens out there work with shorter menus, longer dinners and prices that have not been set by the coach trade. Fewer people book them, which is mostly a matter of distance rather than quality.
Of the 13 communes we have mapped within 90 minutes of Florence, 10 qualify as towns with a serious restaurant that eat well: each holds a restaurant listed by the most demanding of the guides, and a dining guide has named a table in each. The smallest, Castellina in Chianti, has 2,605 residents.
Elsewhere in the catalogue: The best hidden hill towns within 90 minutes of Florence and The best hill towns worth staying overnight within 90 minutes of Florence.
All the towns within a day trip: day trips from Florence.
1. Poppi
Best for walks in a national park. Part of the comune lies in a national park.
1 h 4 min from Florence · homes €1,000 to €1,300 a m² in the center · 5,744 people
Why visit Poppi
Poppi rises above the upper Arno in the Casentino, the wooded valley set between Pratovecchio and Bibbiena. The Counts Guidi held this hill from at least 1169, and the castle they raised across the late twelfth and thirteenth centuries is attributed in its older part to Lapo di Cambio and in the later upper section to Arnolfo di Cambio.
Dante Alighieri, who fought below the hill as a young man, returned to it later as a guest of the Guidi during his exile, so the borgo held him twice, once as a soldier and once as a household guest. The town itself sits above the battle plain, the abbey church inside the walls, the castle over both.
A further Romanesque pieve stands a short distance off, and the forested ridges of the Apennine watershed rise to the east, the same terrain the Guidi once ruled from their hill. What the place adds up to is a single family's hold on a valley, visible still in the line from castle to plain to church, with the forest marking where their lordship ran out.
Il Cedro (MICHELIN) and Mater (MICHELIN and L'Espresso) are listed in food guides.
What to see in Poppi
- Castello dei Conti Guidi. The castle keeps a working library and a fourteenth-century chapel frescoed by the school of Giotto, along with a hand-painted model of the battle below, more than four thousand tin soldiers set out on the table.
- Piano di Campaldino. The plain sits directly beneath the castle walls, open ground still readable as a battlefield, with nothing built across it since.
- Abbazia di San Fedele. Romanesque abbey church inside the borgo, with single nave and stone façade, dating from the early twelfth century.
How to get to Poppi
It has its own railway station. Florence is about 1 h 4 min away by road. The full route from Florence.
Our tip
April through June brings the Casentino into clear sun, the beech forests in their first leaf and the upper Arno full from spring rain. July and August are pleasant at 437 meters, never coastal-hot, with the castle and library full of weekend visitors from Florence. September and October are the harvest and chestnut months: the Foreste Casentinesi turn orange in the high cuts above Pratovecchio.
2. Loro Ciuffenna
Best for a walk through the old town. It is on the list of Italy's most beautiful villages.
46 min from Florence · homes €1,200 to €1,550 a m² in the center · 5,914 people
Why visit Loro Ciuffenna
Loro Ciuffenna sits at 330 meters on the western slopes of the Pratomagno, between the Arno valley and the Casentino. The torrent it is named for cuts through the centro storico under a hump-backed stone bridge of Roman origin, remodeled in the Middle Ages.
A water mill on the bank is still in operation, the oldest active mill in Tuscany, dating to the 12th century and used until recently to grind chestnuts into flour. The inhabitants of the castle of Loro were the first to submit to the Florentine Republic in 1306, and the village formed its own statutes as an autonomous comune in 1462.
Two kilometers up the Setteponti road stands the Pieve di San Pietro a Gropina, one of the great Romanesque parish churches of Tuscany, built around the year 1000 over two earlier churches; its circular pulpit, supported by two knotted Lombard columns, is 8th century.
Il Cipresso - Da Cioni (MICHELIN), Osteria del Borro (MICHELIN and Gambero Rosso) and Casa e Ciliegie (Slow Food and Gambero Rosso) are listed in food guides.
What to see in Loro Ciuffenna
- Pieve di San Pietro a Gropina. Romanesque parish church 2 km south of the village, built around 1000 over a 5th-century church and an 8th-century Lombard one with a knotted-column pulpit.
- Ponte sul Ciuffenna. Hump-backed stone bridge of Roman origin crossing the torrent in the centro storico, heavily remodeled in the medieval period.
- Mulino di Loro Ciuffenna. 12th-century water mill on the Ciuffenna, the oldest active mill in Tuscany, traditionally used to grind chestnut flour.
How to get to Loro Ciuffenna
Florence is about 46 min away by road.
Our tip
April through June brings green slopes, mild evenings and water in the Ciuffenna torrent. September and October are the dry months, when the Pratomagno chestnuts ripen and the Setteponti road sees the best light of the year. July and August can push the Valdarno floor into the mid-thirties; the village stays cooler at 330 meters than the plain below, but the centro storico empties in the afternoon hours.
3. Cerreto Guidi
Best for a World Heritage site. UNESCO lists a site in the comune.
50 min from Florence · homes €1,000 to €1,500 a m² in the center · 10,663 people
Why visit Cerreto Guidi
Cerreto Guidi sits at 123 meters above the Padule di Fucecchio, thirty kilometers west of Florence, on the old hunting grounds of the Counts Guidi and later the Medici. Cosimo I commissioned the Villa Medicea here between 1564 and 1567 as a hunting lodge and territorial outpost over the marsh.
The villa is mounted on a scenographic base of four symmetrical ramps of stairs, the ponti medicei, traditionally attributed to Bernardo Buontalenti, designed to raise the perspective plane and the level of the entrance. In 2013 the villa entered the UNESCO list of Medici Villas and Gardens of Tuscany along with twelve others, and it remains one of the few permanently open as a museum, housing the Museo Storico della Caccia e del Territorio since 2002.
The Via Francigena passes a few kilometers south. Isabella de' Medici, daughter of Cosimo I, was strangled in this villa by her husband Paolo Giordano Orsini in July 1576.
PS Ristorante is listed in the MICHELIN Guide and Gambero Rosso.
What to see in Cerreto Guidi
- Villa Medicea di Cerreto Guidi. Hunting villa built for Cosimo I de' Medici between 1564 and 1567, UNESCO World Heritage since 2013, holding the Museo Storico della Caccia.
- Ponti Medicei. Four symmetric ramps of stairs attributed to Buontalenti, supporting the villa above the village and forming its scenographic base.
- Museo Storico della Caccia e del Territorio. Hunting and local history museum housed in the villa since 2002, with weapons, prints and documents from the Medici hunting grounds.
How to get to Cerreto Guidi
Florence is about 50 min away by road.
Our tip
April through June is the easiest time to walk the village and the villa garden, with the Padule di Fucecchio at its greenest. September and October dry the marsh, the harvest in the surrounding Chianti Montalbano vineyards runs through late September. July and August are hot in the lower Arno plain and the villa is the cool place to be; visitor numbers peak around mid-August.
4. Castellina in Chianti
Best for Chianti Classico DOCG. The town gives its name to Chianti Classico DOCG.
1 h 3 min from Florence · homes €1,300 to €1,900 a m² in the center · 2,605 people
Written about. No. 30. Read the letter →
Why visit Castellina in Chianti
Castellina in Chianti sits at 578 meters on the watershed between the Arno and Ombrone basins, fifteen kilometers northwest of Siena and thirty-five south of Florence. Its position on the historic frontier between the two republics shaped the town: it was a Florentine border fortification reinforced in the fifteenth century by Filippo Brunelleschi and Giuliano da Sangallo against firearm warfare.
The Rocca with its fifteenth-century tower dominates the centro storico and now houses the Museo Archeologico del Chianti Senese, opened in 2006. The Via delle Volte runs the length of the eastern wall: an original ancient pomerium, once open to the sky, gradually built over by private houses against the wall and now a covered arcaded passage lined with workshops and trattorie.
The Tumulo Etrusco di Montecalvario, a sixth-century BC tomb with four burial chambers carved on the cardinal axes, sits a kilometer from the centro storico. The Gallo Nero of Chianti Classico DOCG is grown on the slopes below.
Albergaccio di Castellina (MICHELIN and Gambero Rosso), Osteria di Fonterutoli (Gambero Rosso) and Passo dopo Passo Osteria (Gambero Rosso) are listed in food guides.
What to see in Castellina in Chianti
- Rocca di Castellina. Fifteenth-century fortification with imposing keep, now housing the Museo Archeologico del Chianti Senese, opened in 2006.
- Via delle Volte. Covered arcaded walkway along the eastern wall, once an open pomerium, built over by houses pressing against the fortifications and now lined with workshops.
- Tumulo di Montecalvario. Sixth-century BC Etruscan tomb a kilometer from town, with four burial chambers carved on the cardinal compass points, excavated in the early 1900s.
How to get to Castellina in Chianti
Florence is about 1 h 3 min away by road.
✷ We have written about Castellina in Chianti
“The wine is the whole economy of these hills, every village with its own, the region’s name stamped on the most famous red in Italy. Tuscan food runs to cured and roasted meat, so the wine ran red to meet it, lighter than you expect, almost fruity, easy, made to sit beside a steak and not to be lectured about. Here is the only wine knowledge you need on this road: it is all good.”
Read our piece on Castellina in Chianti →Road to Siena | The Long Way Is the Better Way
Our tip
April through June and September into October are the working months on the Chianti watershed: vine work, harvest from mid-September, mild days at 578 meters. The Festa del Vino in the second half of September fills the centro storico for a long weekend. July and August are warmer but stay below the inland Maremma heat, and the Via delle Volte is reliably cool.
5. San Gimignano
Best for a stage of a long walk. The Via Francigena passes through.
1 h 1 min from Florence · homes €2,200 to €3,300 a m² in the center · 7,452 people
Written about. No. 29. Read the letter →
Why visit San Gimignano
San Gimignano sits at 334 meters in the Val d'Elsa, halfway between Firenze and Siena on the medieval pilgrim road to Rome. Patrician families built 72 tower-houses in the twelfth and thirteenth centuries as proofs of wealth and platforms for vendettas; 14 still stand, the tallest being the Torre Grossa at 54 meters.
The town declared independence from the bishops of Volterra in 1199 and grew rich on saffron and Vernaccia, the white wine grown on the surrounding hills and praised since Dante. The Black Death of 1348 broke the boom; San Gimignano lost more than half its population and submitted to Florence.
That collapse is the reason the medieval skyline survived. UNESCO listed the historic center in 1990 as a complete record of feudal architecture.
Roughly three million visitors come each year, more than 400 times the resident population, and the centro storico empties into the surrounding olive groves once the day-trippers leave.
Linfa (MICHELIN), Da Pode (MICHELIN) and San Martino 26 (MICHELIN and Gambero Rosso) are listed in food guides.
What to see in San Gimignano
- Torre Grossa. Fifty-four meter civic tower attached to the Palazzo Comunale, the tallest of the surviving 14, open for the climb to the panoramic terrace.
- Piazza della Cisterna. Triangular medieval square paved in brick around an octagonal well of 1287, lined by tower houses and Romanesque palaces.
- Collegiata di Santa Maria Assunta. Romanesque parish church on Piazza Duomo, walls covered by Bartolo di Fredi and Lippo Memmi frescoes of Old and New Testament scenes.
How to get to San Gimignano
Florence is about 1 h 1 min away by road.
✷ We have written about San Gimignano
“We arrived in the afternoon, into the second half of the day’s crowd. Off-season meant it was groups and guides rather than a flood, but the shops were open and doing their worst, the same garbage souvenirs, the same pasta no one local would eat, and we walked through it the way you walk through a thing you have decided not to let ruin your evening. The towers stood over all of it, indifferent, which is their whole talent.”
Read our piece on San Gimignano →San Gimignano | The Town After Seven
Our tip
April through June and September into October are the months the town is worth a full day rather than three hours. The buses still come, but late afternoon empties the piazzas and lets the towers take their light. July and August push temperatures past thirty and the centro storico becomes uncomfortable between two and six, when the stone radiates heat.
6. Castelnuovo Berardenga
Best for a soak. The comune has thermal baths.
1 h 17 min from Florence · homes €1,000 to €1,500 a m² in the center · 8,851 people
Written about. No. 31. Read the letter →
Why visit Castelnuovo Berardenga
The commune sits east of Siena, where the hills give way to the clay swells of the Crete Senesi. The name comes from the Terra Berardinga, the area controlled in the tenth century by a Frankish nobleman named Berardo, and the borgo grew up around the castle walls the Sienese Republic raised against Florence.
The centro storico, the villa and gardens at its heart, and the surrounding zone of vineyards form one continuous pattern rather than separate parts: fortress town above, wine country falling away below it toward the clay hills. Across the wider territory, 13 castles, 70 churches and 200 farms record the medieval pattern of the Sienese contado, a scatter of small fortified points and parish churches administering land rather than one dominant center.
The place reads as a border post that outlived its military purpose and settled into agriculture and the arts, its castle now a clock tower, its noble villa now a music foundation, its walls now overlooking rows of Sangiovese.
Il Visibilio (MICHELIN and Gambero Rosso), Poggio Rosso (MICHELIN and Gambero Rosso), L'Asinello (MICHELIN and L'Espresso) and 4 more places are listed in food guides.
What to see in Castelnuovo Berardenga
- Villa Chigi Saracini. Eighteenth-century villa and Italian garden inside the centro storico, its park designed by the Sienese composer Guido Chigi Saracini, whose family foundation still runs the Accademia Musicale Chigiana in Siena.
- Torre dell'Orologio. Surviving tower of the fortress, now bearing the civic clock, the highest visible point of the centro storico.
- Chiesa dei Santi Giusto e Clemente. Eighteenth-century parish church with a neoclassical façade, built on the site of an earlier Romanesque pieve.
How to get to Castelnuovo Berardenga
Florence is about 1 h 17 min away by road. The full route from Florence.
Our tip
April through June and September into October are the months Chianti Classico shows best, the green hills moving toward the gold of harvest. The Sagra del Vino runs the second weekend of September. July and August push past thirty and the centro storico empties between two and six; the cellars on the surrounding hills offer cool tastings and longer rentals.
7. Monteriggioni
Best for a slow weekend. The Touring Club gives it its orange flag for small inland towns.
59 min from Florence · homes €1,500 to €2,250 a m² in the center · 9,950 people
Written about. No. 33. Read the letter →
Why visit Monteriggioni
Monteriggioni sits at 274 meters on a natural hillock between Firenze and Siena, eleven kilometers from the Sienese gates. The walls were built between 1213 and 1219, when Siena ran them up as a frontline garrison facing Florentine expansion north.
They are still there. Fourteen square towers, 570 meters of curtain wall, ten meters tall, two gates: Porta Fiorentina to the north, Porta Romana to the south.
Dante used the towers in Inferno XXXI as the image for the giants ringing the central pit of Hell. The fortress was never breached by storm.
Inside, the village is a single irregular Piazza Roma, a Romanesque parish church of Santa Maria Assunta, a few streets that take fifteen minutes to walk end to end. The Via Francigena runs past the southern wall.
The town hosts a medieval festival in early July, when the population inside the walls multiplies for a weekend. The rest of the year, the silence inside the gates is the point.
Futura Osteria (MICHELIN and Gambero Rosso) and Osteria Bottega dell'Abate (Gambero Rosso) are listed in food guides.
What to see in Monteriggioni
- Mura di Monteriggioni. Circular 570-meter wall built 1213-1219 by the Sienese, fourteen square towers on equidistant bases, ten meters high, intact.
- Piazza Roma. Single main square inside the walls, ringed by stone houses, with the Romanesque parish church on the north side.
- Chiesa di Santa Maria Assunta. Romanesque parish church on Piazza Roma, plain stone façade, single nave, the only significant religious building inside the walls.
How to get to Monteriggioni
It has its own railway station. Florence is about 59 min away by road. The full route from Florence.
Our tip
April through June and September into October are the months when the walls and the Chianti ridge behind them sit at their best, before the heat closes in. The Festa Medievale takes the second weekend in July, three days of costumed reenactment and feasting inside Piazza Roma, when the village population multiplies. July and August are hot and the day-tripper buses from Firenze and Siena fill the gates between ten and four.
8. Siena
Best for a wine weekend. It belongs to the national association of wine towns.
1 h 13 min from Florence · homes €2,400 to €4,200 a m² in the center · 52,990 people
Written about. No. 35. Read the letter →
Why visit Siena
Siena sits at 322 meters on three hills fifty kilometers south of Florence, with which it fought a defining rivalry through the thirteenth and fourteenth centuries. The historic center has been UNESCO World Heritage since 1995, preserved as a medieval city that worked deliberately to differ from Florentine urban planning.
Piazza del Campo, the shell-shaped square at the meeting point of the three original hills, fans out toward the Palazzo Pubblico, whose construction began in 1297. The Torre del Mangia next to it, built between 1338 and 1348, stands 87 meters tall, the exact height of the Duomo, a deliberate equality between church and state.
The Duomo itself, marble-clad in horizontal black and white bands, holds the inlaid mosaic floor that Vasari called the most beautiful ever made, and sculptures by Donatello, the Pisano family and Michelangelo. The Palio runs twice a year, on 2 July and 16 August: bareback riders representing seventeen contrade circle the Campo three times in roughly ninety seconds.
Ristorante Al Mangia (Locali Storici), Osteria le Logge (MICHELIN and Gambero Rosso), Campo Cedro (MICHELIN and Gambero Rosso) and 3 more places are listed in food guides.
What to see in Siena
- Piazza del Campo. Shell-shaped medieval square at the meeting point of Siena's three hills, paved in 1349 in red brick divided into nine sectors for the Council of Nine.
- Palazzo Pubblico. Town hall begun in 1297, with the Sala dei Nove holding Lorenzetti's Allegory of Good and Bad Government from 1338-1339.
- Torre del Mangia. Brick tower built 1338-1348 next to the Palazzo Pubblico, 87 meters tall, set deliberately to match the height of the Duomo.
How to get to Siena
It has its own railway station. Florence is about 1 h 13 min away by road. The full route from Florence.
✷ We have written about Siena
“Before Florence was the banking capital of the known world, the bench belonged to Siena. The word itself comes from the bench, the banco, where the money changers sat, and in the twelfth century, the Sienese ran some of the largest banking houses in Europe, moving the money of popes and kings while Florence was still finding its feet.”
Read our piece on Siena →Siena | What you are really here for
Our tip
April through June and September into October are the dry months in central Tuscany: mild days, full openings at the museums, the Campo busy but not packed. The Palio runs on 2 July and 16 August: the city stops for the four days around each race, the trial races fill the piazza twice a day, and accommodation books out a year ahead. July and August are otherwise hot and crowded with day-trippers from Florence.
9. Arezzo
Best for everyday life on foot. Eight of the ten everyday services we look for are mapped within 500 meters of the center.
1 h 2 min from Florence · homes €1,600 to €2,000 a m² in the center · 96,479 people
Written about. No. 36. Read the letter →
Why visit Arezzo
The city sits on a Tuscan hilltop 80 km southeast of Florence, and the ground beneath it holds one of the densest layers of Etruscan, Roman, medieval and early-Renaissance building anywhere in the region, without the tour-bus crush of its more famous siblings. The lower streets and the upper square pull the town's whole history together: the Pieve di Santa Maria's Romanesque exterior and five-tier facade were widely copied across central Italy, the Cattedrale di San Donato is Gothic with stained glass by Guillaume de Marcillat, and the Casa Vasari is the painter-architect's own house, frescoed by himself.
Giorgio Vasari was Arezzo's other native son, and beyond his own house his Loggia still frames one side of the sloped trapezoidal square, alongside the 14th-century facade of the Palazzo della Fraternita dei Laici and the Romanesque apse of the Pieve. The Museo Archeologico Nazionale stands on the site of the Roman Amphitheatre, where the Vasi corallini, coral-red glazed Roman pottery, were made as a manufacturing center for the empire.
The fresco cycle narrates the journey of the Cross from Adam's grave through Solomon to Constantine to Heraclius in 10 panels of geometric serenity and silver-grey light, and the film that made the square famous used its slope as a stage set, the same slope the antique dealers now fill every first weekend of the month with more than 500 stalls drawing buyers from across Europe. Twice a year, in June and September, the four city quartieri, Porta Crucifera, Porta del Foro, Porta Sant'Andrea and Porta Santo Spirito, meet in the jousting tournament, riders charging the wooden target on horseback in a contest revived as a historical pageant in 1931.
The food is Tuscan: pici with hare ragù, ribollita, bistecca chianina from the Val di Chiana below the city, Pecorino Toscano, with Vino Nobile, Brunello and Chianti Classico all within an hour's drive south. Together the fresco, the square, the joust and the antique trade give the city a working civic life built on Renaissance art and medieval ritual rather than a museum piece preserved around it.
Buca di San Francesco (Locali Storici and Gambero Rosso), Caffè dei Costanti (Locali Storici), Osteria Grande (MICHELIN and Gambero Rosso) and 3 more places are listed in food guides.
What to see in Arezzo
- Piero della Francesca's Leggenda della Vera Croce. 10-panel fresco cycle in the Cappella Bacci of San Francesco. Timed entry: 25 people, 30 min, book 2-3 weeks ahead.
- Piazza Grande + Pieve di Santa Maria. Sloped trapezoidal square lined by the Palazzo della Fraternita, Vasari's Loggia, and the 12th-c Lombard-Romanesque apse of Santa Maria.
- Fiera Antiquaria (every first weekend). 500+ dealers fill the square and surrounding streets, drawing dealers and buyers from across Europe.
How to get to Arezzo
It has its own railway station. Florence is about 1 h 2 min away by road. The full route from Florence.
✷ We have written about Arezzo
“Arezzo is the last of this region’s losers, the cousin of Siena, beaten and absorbed and left behind, and like all of them, it kept what the winners spent. The same edge that cost it an empire is the moat that keeps the tour buses in Florence. It does not perform. It does not sell you a lie about itself. It works its gold, runs its schools, and lets the heat sit on the great empty square, and it will not notice whether you stay a day or a life.”
Read our piece on Arezzo →Arezzo | The City That Ignores You
Our tip
Arezzo is best April–June and September–October. The Fiera Antiquaria's first weekend of the month is the year-round draw (book hotels 2 weeks ahead). The Giostra del Saracino (third Saturday June + first Sunday September) is the year's two civic highlights.
10. Fiesole
Best for a day out from Florence. It is 24 min by car.
24 min from Florence · homes €2,250 to €3,400 a m² in the center · 13,809 people
Why visit Fiesole
Fiesole was Viesul to the Etruscans and Faesulae to the Romans, who took it in 283 BC. Florence claimed it in 1125 and never let it go, which is the reverse of the usual order: the hill town came first, the valley city second, and the ridge has watched its own successor grow across the centuries since.
The convent that crowns the highest point sits at 345 meters. Today the town functions as the hill seat of Florentine villas, the Villa Medici among them, so the relationship between Fiesole and Florence is not just historical but residential: those with means built upward, toward the older settlement, to look down on the newer one.
Serrae Villa Fiesole (MICHELIN and Gambero Rosso) and Le Lance di Fiesole (Gambero Rosso) are listed in food guides.
What to see in Fiesole
- Teatro Romano. Stone tiers set into the hillside below the cathedral, still used each summer for the Estate Fiesolana, so the seats fill for performances the way they once did in antiquity.
- Cattedrale di San Romolo. Romanesque cathedral founded in 1028, flanked by a 42-meter bell tower, with a marble altar from 1273 and two Pietro Perugino frescoes.
- Convento di San Francesco. Romanesque-Gothic Franciscan convent at the ridge's highest point, 345 meters, with cloisters and a panoramic view back over Florence.
How to get to Fiesole
It has its own railway station. Florence is about 24 min away by road. The full route from Florence.
Our tip
April through June and September through October are the months Fiesole was built for: the air cooler than Florence by three to five degrees, the cypress alleys clean of haze, and the Roman theater season runs through July and early August with concerts under the open sky. July and August push the day temperature high enough that even the hilltop feels heavy at midday, though the evenings come back. November through March is quiet, light hits the cathedral late and low, and the wood-burning trattorias around Piazza Mino do their best work.
If you only pick one
Which town is yours
One town for each kind of trip, and the reason in a line.
Without a car
Arezzo
The train stops in the commune, so you can arrive and leave without a car.
For everyday life on foot
Siena
Nine of the ten everyday services we look for, from a grocer to a pharmacy, are on the map within 500 meters of the center.
For the food
Castellina in Chianti
Home of Chianti Classico DOCG. One of the founding Chianti Classico communes; central, on the watershed between the Arno and the Ombrone.
For a short trip
Fiesole
24 min by car from Florence, the shortest drive from a city on this list.
For a small town
Poppi
5,744 people, the smallest town on this list.
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