The 8 Best Small Towns in Tuscany for Hill-Town Magic, Wine, and Slow Days
Walled medieval villages, vineyard-draped ridgelines, and town squares built for lingering: these are the Tuscan towns worth driving the back roads for.
Discover the charm of San Gimignano with its medieval towers and beautiful Tuscan landscape. · Oskar Gross
Tuscany's big names get the crowds, but its soul lives in the small towns: hilltop villages ringed by stone walls, where the morning starts with espresso in a sloping piazza and ends with a glass of local red as the sun drops behind the cypresses. These are places measured in footsteps, not bus schedules, and an afternoon spent wandering one of them tells you more about the region than a week of ticking off galleries.
This list ranks eight towns that reward the detour, chosen for their atmosphere, their food and wine, and how easy they are to fold into a Tuscan road trip. Some are walled medieval showpieces, others are wine capitals where the cellars run beneath the streets. All are real, lived-in towns, not museum pieces.
Use it to build an itinerary: pair a couple of Val d'Orcia towns in the south with a Chianti village or two near Florence, rent a car if you can (the countryside between them is half the reward), and don't rush. The best moments here are unscheduled.
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1
San GimignanoCentral Tuscany, about 1 hour southwest of Florence Google
Famous for its skyline of medieval stone towers, San Gimignano looks like a fortified Manhattan dropped into the Tuscan hills, the survivors of dozens built by rival families showing off their wealth. Within the walls, Piazza della Cisterna and Piazza del Duomo form a connected pair of squares lined with gelaterie, wine bars, and Romanesque facades. The town is the home of Vernaccia di San Gimignano, Tuscany's celebrated white wine, best sampled in a small enoteca before the day-trip coaches arrive or after they leave. Come early or stay overnight to have the lanes to yourself at golden hour.
- The towers and the view from Torre Grossa
- Vernaccia di San Gimignano white wine
- Gelateria Dondoli on Piazza della Cisterna
- Frescoes inside the Collegiata
Best for: first-time visitors and photographers
Getting there: About 1 hour by car from Florence, or bus via Poggibonsi (roughly 1.5 hours with the connection)
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2
MontepulcianoVal di Chiana, southern Tuscany, about 1.5 hours southeast of Florence Google
Stretched along a high ridge, Montepulciano is a Renaissance town with calf-burning streets that climb to a handsome main square framed by palazzi and a cathedral. Its real fame is the wine: Vino Nobile di Montepulciano, an elegant Sangiovese-based red poured in historic cellars carved deep into the rock beneath the town. Duck into one of the cantine like Contucci or De' Ricci to taste straight from the barrel in vaulted underground cellars. Film fans will recognize the streets and the nearby San Biagio church from the Twilight saga.
- Vino Nobile tasting in an underground cellar
- Piazza Grande at the top of town
- Tempio di San Biagio just below the walls
- Pici pasta with local ragu
Best for: wine lovers and slow strolls
Getting there: About 1.5 hours by car from Florence; by train to Chiusi-Chianciano then a local bus (roughly 2.5 hours total)
3
PienzaVal d'Orcia, southern Tuscany, about 1.5 hours south of Florence Google
Tiny, perfect Pienza was rebuilt in the 15th century as Pope Pius II's vision of the ideal Renaissance town, and the compact center is now a UNESCO World Heritage Site. The reward is twofold: harmonious squares and palazzi you can walk in twenty minutes, and some of the best views in Tuscany from the ramparts overlooking the Val d'Orcia's rolling, cypress-lined hills. Pienza is also pecorino country, and shops along the main street sell the sheep's-milk cheese aged in everything from ash to walnut leaves. Walk the aptly named Via dell'Amore at sunset for the postcard panorama.
- Pecorino di Pienza cheese tasting
- Val d'Orcia views from the town walls
- Piazza Pio II and the cathedral
- Cypress-lined country roads nearby
Best for: food lovers and romantic getaways
Getting there: About 1.5 hours by car from Florence; easiest with your own vehicle
4
MontalcinoVal d'Orcia, southern Tuscany, about 1.5 hours south of Florence Google
Crowned by a 14th-century fortress, Montalcino is the home of Brunello, one of Italy's most prestigious and age-worthy red wines. The medieval center is genuinely small, but the surrounding hills are wall-to-wall vineyards, and you can taste Brunello and its younger sibling Rosso di Montalcino in the enoteca built right into the fortress walls. Beyond the wine, the views over the Val d'Orcia and the nearby Romanesque Abbey of Sant'Antimo are worth the drive on their own. It is quieter and less touristy than its fame suggests.
- Brunello di Montalcino tasting in the Fortezza
- Abbey of Sant'Antimo in the valley below
- Panoramic ramparts walk
- Wild boar (cinghiale) specialties
Best for: serious wine drinkers
Getting there: About 1.5 to 2 hours by car from Florence; a car is strongly recommended
5
CortonaEastern Tuscany, about 1.5 hours southeast of Florence Google
Perched high above the Val di Chiana with views stretching to Lake Trasimeno, Cortona is the hill town made famous by Under the Tuscan Sun, and it lives up to the billing without feeling staged. Etruscan in origin, it has steep stone streets, a lively central piazza, and a small but excellent museum holding Etruscan bronzes and a Fra Angelico Annunciation. Evenings here are unhurried: aperitivo on Piazza della Repubblica, then dinner of fresh pici or local beef. The climb up to the Basilica di Santa Margherita rewards you with one of the widest views in the region.
- MAEC Etruscan museum
- Sunset views over Lake Trasimeno
- Piazza della Repubblica aperitivo
- Fra Angelico's Annunciation in the Diocesan Museum
Best for: a relaxed overnight and panoramic views
Getting there: About 1.5 hours by car; or train to Camucia-Cortona then a short bus up the hill (roughly 1.5 to 2 hours)
6
VolterraBetween Florence and the coast, about 1.5 hours southwest of Florence Google
Set on a dramatic, windswept hilltop, Volterra feels older and rawer than the polished tourist towns, with Etruscan walls, a remarkably intact Roman theater, and a hilltop fortress still in use. It has been a center of alabaster carving since Etruscan times, and you can watch artisans shape the translucent stone in workshops around town. The Guarnacci Museum holds one of Italy's finest Etruscan collections, including the haunting, elongated bronze figure known as the Shadow of the Evening. Fewer crowds and a moodier atmosphere make it a favorite for travelers who want substance over selfies.
- Roman theater ruins
- Guarnacci Etruscan Museum
- Alabaster artisan workshops
- Medieval Piazza dei Priori
Best for: history buffs and crowd-avoiders
Getting there: About 1.5 hours by car from Florence; public transport is slow, so a car is best
7
Greve in ChiantiChianti, about 45 minutes south of Florence Google
The unofficial capital of the Chianti wine region, Greve is an easygoing market town built around a funnel-shaped, arcaded square, Piazza Matteotti, ringed with wine shops and trattorias. It makes the ideal base for exploring the vineyards between Florence and Siena, and the historic butcher Antica Macelleria Falorni is a destination in itself for cured meats and the famous local finocchiona salami. The Saturday market and a constant calendar of food and wine events keep it lively. From here, scenic back roads lead to tiny hamlets like Montefioralle and Panzano.
- Piazza Matteotti and its wine shops
- Antica Macelleria Falorni for salumi
- Chianti Classico tastings
- Day trips to Montefioralle and Panzano
Best for: a Chianti wine base close to Florence
Getting there: About 45 minutes by car from Florence; SITA bus from Florence takes around 1 hour
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8
MonteriggioniNear Siena, about 1 hour south of Florence Google
Small enough to walk in minutes but unforgettable from a distance, Monteriggioni is a perfectly preserved 13th-century walled village crowning a low hill, its ring of towers so striking that Dante compared them to giants. Inside the walls there is essentially one square, a church, a couple of restaurants, and a sense of stepping fully into the Middle Ages. You can walk a stretch of the ramparts for views over the vineyards and the old Via Francigena pilgrim route. It pairs naturally with nearby Siena or San Gimignano on the same outing.
- Walking the medieval walls and towers
- Piazza Roma in the village center
- Medieval festival in summer
- Views over the Via Francigena countryside
Best for: a quick, atmospheric stop
Getting there: About 1 hour by car from Florence; often combined with Siena and San Gimignano on a day tour
Good to Know
Getting around A rental car transforms a Tuscan hill-town trip, especially for the Val d'Orcia (Pienza, Montalcino) and Chianti, where buses are infrequent. Park in the lots outside the walls, marked with blue lines or designated tourist parking, as town centers are largely pedestrian or restricted ZTL zones.
When to go Late spring (May to mid-June) and September offer warm days, green hills, and manageable crowds. Avoid the August heat and Italian holiday week around Ferragosto, when many family-run trattorias close.
Beat the crowds The famous towns like San Gimignano fill with day-trippers from mid-morning to late afternoon. Arrive before 10am or stay overnight to experience the lanes when they are quiet and the light is best.
Book tastings ahead Top cellars in Montepulciano and Montalcino, and the best wineries in Chianti, often require reservations, particularly on weekends. Email or call a day or two ahead rather than relying on walk-ins.
Tuscany's small towns are best taken slowly, two or three at a time, with long lunches and unplanned detours down cypress-lined roads in between. String together a southern loop through the Val d'Orcia and a northern one through Chianti, give yourself at least one overnight in a walled village, and let the region set the pace. Plan your route, book your tastings, and the rest of the magic takes care of itself.