The best towns on a walking route that are worth a night in Tuscany
90 towns visited, 910 to go. Follow along, free: Subscribe on Substack
Walking Toscana is a matter of surfaces underfoot: white gravel roads through the Val d'Orcia, chestnut woods above the Versilia plain, pale sandstone lanes that hold the heat well past sunset. The historic routes, the Via Francigena chief among them, string together towns built of the stone quarried nearest to them, so the color of the buildings changes as the days pass. Spring brings green wheat and cold mornings; September brings the grape harvest and evenings warm enough to eat outside. Dinner at the end of a stage tends toward the plain and the filling, pici with garlic, ribollita, pecorino with chestnut honey, a bottle of something from the hill you crossed that afternoon.
People come to Toscana and go to Florence, and Florence rewards them, but the queue for the Uffizi now runs the length of the loggia in every month with sun in it, and the city has largely stopped being a place you can walk out of on foot. The day trips radiate outwards by coach and return by dark, which means the countryside is visited in daylight and emptied at dinner. That rhythm makes the region feel busier than it is.
The routes carry on past all of that, and they were laid out for people moving slowly with somewhere to sleep at the end. These are the towns where the stage stops: walled, hilltop, or set beside hot water, each with a bed worth booking rather than a car park to leave from. Arrive in the late afternoon, when the coaches have gone, and the town returns to the people who live in it.
Of the 84 communes we have mapped in Toscana, 7 qualify as towns on a walking route worth staying overnight: each is a stage on one of the long historic walking routes, and each has a hotel a travel guide has vouched for. The smallest, San Casciano dei Bagni, has 1,500 residents.
Elsewhere in the catalogue: The best towns with a World Heritage site that are worth a night in Tuscany and The best towns on a walking route in the province of Siena.
Why visit San Casciano dei Bagni
San Casciano dei Bagni sits at 582 meters at the southern edge of the province of Siena, above 42 hot springs that average 42 degrees Celsius. The baths were used continuously from Etruscan through Roman times and again from the Renaissance, when visitors came from across Europe.
In 2022, an excavation that began in 2019 at the ancient sanctuary turned up 24 bronze votive statues protected by mud, with around 6,000 coins in gold, silver and bronze. The find was the largest of its kind in fifty years; most surviving Etruscan votive material is terracotta.
The 1,500 residents live on a basalt outcrop above the Roman thermal complex, in a centro storico of stone houses and three small churches. The borgo joined the Borghi più belli network in 2014 and remains one of the smallest communes in Toscana to carry both that label and Bandiera Arancione.
What to see in San Casciano dei Bagni
- Santuario Ritrovato. Etruscan-Roman thermal sanctuary excavated since 2019, where 24 bronze votives and around 6,000 coins were recovered in 2022.
- Bagno Grande. The principal natural pool of the 42 hot springs, used from the second century BC through the Renaissance and reopened to the public.
- Collegiata di San Leonardo. Romanesque parish church in the centro storico, restored in the seventeenth century, with a baptismal font carved from local travertine.
How to get to San Casciano dei Bagni
Perugia is about 1 h 8 min away by road.
Our tip
The thermal pools make the calendar different here. Winter is the season many visitors prefer, when the 42-degree water steams against cold air and snow occasionally dusts the basalt outcrop. April through June and September into October are the most balanced months: warm hill light, the dry-stone walls of the borgo at their best, the sanctuary excavations open to guided tours.
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.
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
Firenze 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.
Why visit Montalcino
Montalcino sits at 564 meters on a hill south of Siena, the centro storico ringed by walls and crowned by a pentagonal fortress built in 1361. When Florence took Siena in 1555, the Sienese exiles regrouped here and held out for almost four years; the Rocca itself never fell.
That date matters less to most visitors than 1980, when Brunello di Montalcino was named one of the first four Italian wines to receive DOCG status. The vineyards run from the town at 600 meters down to plots at 200, on stony galestro soils that ripen Sangiovese Grosso into a wine that ages for decades.
The Abbey of Sant'Antimo, ten kilometers south, is a Romanesque church first documented in 814 and tied by local legend to a vow by Charlemagne. The town also produces miele, olio, and the white truffles of the surrounding woods.
It holds seven designations at once: UNESCO (as part of the Val d'Orcia), Bandiera Arancione, Città del Vino, Città dell'Olio, Città del Miele, Città del Tartufo and the Via Francigena.
What to see in Montalcino
- Rocca di Montalcino. Pentagonal fortress built in 1361 by Sienese architects Mino Foresi and Domenico di Feo, refuge of the Sienese Republic after 1555.
- Abbazia di Sant'Antimo. Romanesque abbey ten kilometers south, first documented in 814, set among olive groves below the town with Gregorian chant still sung.
- Palazzo dei Priori. Thirteenth-century town hall on Piazza del Popolo, slender tower attached, civic seat of the medieval commune.
How to get to Montalcino
Perugia is about 1 h 45 min away by road. The full route from Florence.
Our tip
April through June and September into October are the months locals prefer. The hills are green or gold depending on the half, and the vineyards run their full work cycle. The Sagra del Tordo, a medieval archery contest between the four quarters of the town, takes place the last Sunday of October.
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.
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
Firenze 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.
Why visit Camaiore
Camaiore stretches from the Apuan Alps to the Versilia coastline, the only Versilia commune with substantial territory in both. The town center sits at 34 meters on the alluvial plain, named Campus Maior by the Romans for a military encampment on the road from Lucca to Luni.
That name and that road explain the town's shape: a fixed inland center built around the Collegiata and the medieval grid, connected by the Via Francigena to a coast six kilometers away that the Romans never had reason to build toward. The inland town and the beach at Lido di Camaiore function as two settlements under one name, joined by the road rather than by contiguous streets, with the Apuan Alps visible from the shore as the backdrop to both.
A commune this shape, mountain territory, a Roman road town, and a beach at the end of it, holds together not because its parts resemble each other but because each has stayed distinct while remaining reachable from the others.
What to see in Camaiore
- Collegiata di Santa Maria Assunta. Thirteenth-century parish church with a fourteenth-century bell tower, the central religious building of the inland town.
- Badia di San Pietro. The church stands alone now, a single Romanesque nave where a monastery once stood, its stone unadorned in the way that marks the Lombard-era Benedictine houses of the region.
- Lido di Camaiore. Fine sand six kilometers from the town center, with the Apuan Alps rising directly behind it, mountain and shoreline visible in the same view.
How to get to Camaiore
It has its own railway station. Pisa is about 44 min away by road. The full route from Pisa.
✷ We have written about Camaiore
“I watched eight old men stand up at once, and something in me quietly rearranged itself. They had been sitting at Caffè Celero on Piazza San Bernardino for most of an hour, maybe longer, doing what men over sixty do on an Italian piazza, which is nothing, but nothing done carefully and particularly.”
Read our piece on Camaiore →I Could Get Old Here
Our tip
May through September runs the Versilia season at the Lido and gives the inland town its share of light evenings. June and September are the quieter brackets: warm enough for the sea, cool enough to walk the Francigena stages without losing the morning. July and August fill the Lido with families from Lucca and Milan, parking gets tight, and the inland piazze stay calmer than the seafront.
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.
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. Firenze 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.
Why visit Lucca
Lucca sits at 19 meters on the Serchio plain, a Roman colony from 180 BC laid out in a grid still visible in the centro storico. The current walls run four kilometers around the city, twelve meters high and thirty meters wide, built between 1513 and 1645 and never breached.
They are now a tree-lined elevated promenade circling the old city, and one of the only complete Renaissance city walls left in Italy. The Piazza dell'Anfiteatro preserves the elliptical footprint of a second-century Roman amphitheater that once held ten thousand spectators; the ring of houses follows the arena's exact shape.
The Cattedrale di San Martino holds the Volto Santo crucifix and Jacopo della Quercia's tomb of Ilaria del Carretto. Giacomo Puccini was born here in 1858.
The town gets the Lucca Comics & Games festival every October-November, the largest comics convention in Europe at 300,000 attendees.
What to see in Lucca
- Mura di Lucca. Four kilometers of intact sixteenth-century walls, 12 meters high and 30 meters wide, built 1513-1645, now an elevated tree-lined promenade.
- Piazza dell'Anfiteatro. Elliptical square preserving the footprint of a second-century Roman amphitheater that once seated ten thousand.
- Cattedrale di San Martino. Eleventh-century cathedral with a Romanesque-Gothic façade, the Volto Santo crucifix and Jacopo della Quercia's tomb of Ilaria del Carretto from 1406.
How to get to Lucca
It has its own railway station. Pisa is about 34 min away by road. The full route from Pisa.
✷ We have written about Lucca
“We came in through Porta Santa Maria on a Tuesday afternoon in February, with the sun low and the wind off the Apuane sharp enough to flatten Sophia's coat against her, and there was nobody there. A man in a green trench was walking a dog. Two old women were having a conversation on a bench inside the wall, slowly, in dialect, with long pauses.”
Read our piece on Lucca →Lucca | The City You Cannot Photograph
Our tip
April through June and September through October bracket the year. May is the Lucca Classica music festival and the Lucca Biennale Cartasia in even years. October-November brings Lucca Comics & Games and the centro storico fills with around 300,000 attendees; book a year ahead.
More from Anywhere Italy
- The best towns with a World Heritage site that are worth a night in TuscanyTuscanyworth staying overnightWorld Heritage6 towns · smallest 1,976 residents
- The best towns on a walking route in the province of SienaSiena provinceon a walking route10 towns · smallest 1,060 residents
- The 6 best towns on a walking route that eat well in the province of SienaSiena provinceon a walking routeeats well6 towns · smallest 1,500 residents
- The best wine towns worth staying overnight in TuscanyTuscanywineworth staying overnight8 towns · smallest 1,500 residents
- The best towns worth staying overnight in the province of SienaSiena provinceworth staying overnight8 towns · smallest 1,500 residents
- The 9 best hidden hill towns on a walking route in TuscanyTuscanyhill townon a walking routehidden8 towns · smallest 1,060 residents