Tuscany's hill towns are extraordinary and overcrowded in August. Here is the complete guide with the timing and sequencing that makes them enjoyable.
Plan my Italy trip →Tuscany has the highest density of extraordinary hill towns in Italy — each on its own promontory, each with its distinct food, wine, and medieval heritage, and each with the specific Tuscan landscape (the Val d'Orcia cypress rows, the Crete Senesi clay hills, the Chianti vineyard sequence) as backdrop. Here is the complete honest guide to the finest — with the specific quality of each that makes it worth the detour from the obvious route.
Volterra (Pisa province, 531m — the deepest Etruscan town in Tuscany): Volterra has been continuously inhabited since the Villanova period (9th century BC) — the specific Etruscan city (Velathri) was one of the twelve federated cities of the Etruscan League and one of the largest in the 4th-3rd century BC, with 25,000 inhabitants. The Etruscan walls (partially surviving — the Porta all'Arco, the 4th-3rd century BC city gate with three carved heads on the keystone, is the finest surviving Etruscan dressed-stone gate in Italy), the Museo Guarnacci (the most complete Etruscan archaeological collection in any Tuscan hill town, with the funerary urn of the "Evening Shadow" — the elongated bronze figure that inspired Alberto Giacometti's sculptural style), and the alabaster workshop tradition (Volterra is the only Italian city where alabaster carving is a continuous craft tradition from the Etruscan period — the Etruscan funerary urns in the Guarnacci are carved from the same local alabaster that the current workshops use) make Volterra more historically layered than any comparable Tuscan hill town. The Balze (the clay erosion cliffs on the western side of the town, where the soft substrate beneath the rock has been progressively eroding and dropping the cliff edge toward Volterra — a church and sections of the Etruscan walls have already fallen over the Balze in the historical record) are the most dramatic geological feature in Tuscany. Montepulciano (Siena province, 605m — the Vino Nobile capital): The Vino Nobile di Montepulciano DOCG (the Prugnolo Gentile (Sangiovese clone) wine from the Montepulciano commune — the "Barolo of the south" epithet is applied also to this, but it is a different wine from the Taurasi or the Brunello) and the specific urban quality of the main street (the Corso — a steep climb from the Porta al Prato gate to the Piazza Grande at the summit, with the characteristic palazzo sequence of a Renaissance hill town) make Montepulciano the best combined wine-town experience in the Val d'Orcia. The Palazzo Tarugi (the Renaissance palazzo with the lion-and-griffin-supported wellhead in the adjacent Piazza Grande — the finest palazzo in Montepulciano) and the Duomo (with Taddeo di Bartolo's "Assumption of the Virgin" altarpiece (1401) — one of the finest late Sienese school altarpieces in the region). The cantina visits: the Cantine Contucci (in the palazzo basement, the oldest winery in Montepulciano — visits by appointment, specific Vino Nobile aging seen in situ) and Avignonesi (the most innovative estate, with a 25-year Vin Santo (the rare late-harvest wine that aged in small barrels for 10 years) available for tasting at the farmhouse 2km from town). Pienza (Siena province, 491m — the ideal Renaissance city): Pope Pius II (Enea Silvio Piccolomini, 1405-1464) was born in the village of Corsignano, on the Val d'Orcia ridge, and on his election as pope in 1458 commissioned the architect Bernardo Rossellino to transform his birth village into a model Renaissance city — the project was completed in just 3 years (1459-1462), creating the first planned Renaissance urban environment in Italy. The specific Pienza achievement: the Piazza Pio II (the main piazza, flanked by the Cathedral, the Palazzo Piccolomini (the pope's family palace), the Palazzo Vescovile, and the Palazzo Comunale — four different building types forming a coherent ensemble) is the only Italian piazza entirely designed by a single architect for a single patron in a single campaign. UNESCO World Heritage since 1996. The Pecorino di Pienza DOP (the cave-aged sheep's milk cheese available from the Via dell'Amore shops at €14-22/kg) is one of the finest Italian DOP cheeses.
Pitigliano (Grosseto province, on a tufa cliff in the Maremma hills near the Lazio border) has been called "Piccola Gerusalemme" (Little Jerusalem) since the 16th century, when the Orsini lords of Pitigliano offered Jewish refugees from the Papal States (where Jews were being progressively expelled and ghettoized under Papal policy from 1555 onward — Pope Paul IV's "Cum nimis absurdum" bull requiring Roman Jews to live in ghettos) protected residence in exchange for their commercial and financial skills. The Pitigliano Jewish community, established from the 1560s and growing through the 17th and 18th centuries, built a complete Jewish institutional infrastructure within the cave-cut tufa city: the Synagogue (the current building dated to 1598, restored after WWII — the oldest continuously active synagogue in Tuscany, the guided visit is €5 and includes the adjacent mikve (ritual bath), the kosher bakery, and the rabbi's archive); the Jewish cemetery (on the tufa cliff below the town); and the specific kosher food traditions that survive as a Pitigliano culinary heritage (the sfratto — a honey-walnut filled pastry of Jewish origin, now produced by the town's bakeries as both a Jewish festival food and a tourist specialty). The specific Pitigliano Jewish history: the community was protected from both the expulsions of 1622 and the Fascist racial laws (1938) by the specific tolerance of the local population — Pitigliano had no SS deportation round-up during WWII (unlike many other Tuscan communities) because the local population concealed Jewish families in the tufa cave system below the town. The community diminished through emigration and assimilation from the 19th century onward and has fewer than 10 practicing Jewish community members today — but the physical infrastructure of the historical Jewish presence is the most complete surviving example in rural Tuscany.
Twelve genuinely extraordinary Italian experiences outside the standard tourist circuit: (1) The Frasassi Caves (Genga, Marche): the largest cave complex open to the public in Italy — the Sala della Bora chamber (180m wide, 200m long, 100m high) is large enough to contain Milan's Duomo cathedral with room to spare. The 1.5km guided circuit (€15, 1h30) through the stalactite and stalagmite formations gives the most dramatic underground experience in Italy. Only 300,000 visitors per year vs 4 million at Pompeii. (2) The Trabocchi Coast (Chieti, Abruzzo): the Adriatic coast road between Francavilla al Mare and Vasto with the specific trabocchi — the wooden fishing platforms on stilts extending 20-30m over the sea, traditional Abruzzese fishing structures converted to seafront restaurants where you eat above the Adriatic water. The Via Verde dei Trabocchi (the 42km coastal cycling path connecting the trabocchi) is the finest Italian coastal cycling trail. (3) The Gole del Raganello (Civita, Calabria): the most spectacular canyon in the Pollino National Park — guided rafting and canyon hiking through a 600m-deep gorge accessible from the Arbëreshë village of Civita (see the Calabria small towns guide). (4) The Alberese horse riders (Grosseto, Tuscany): the Parco Regionale della Maremma cattle drive — the butteri (the Maremma cowboys, the only surviving cattle driver tradition in continental Europe) ride the Maremma coast marshes with the longhorn Maremmana cattle each Saturday morning. Organized observation from horseback is available through the park administration. (5) The Infiorata di Spello (Spello, Umbria — Corpus Christi, June): the streets of the Umbrian hill town of Spello are carpeted in flower petal patterns 15cm deep, covering the entire historic center — a flower carpet tradition (the infiorata) dating to the 18th century, in which the entire town community participates in the creation of designs that take 6-8 hours to complete and are then processed over by the Corpus Christi procession within 2 hours. The visual quality at dawn (before the procession), when the designs are complete and the streets undisturbed, is the finest single aesthetic event in Umbria. (6) The Sassi di Matera night walk (Matera, Basilicata): the Sassi viewed from the Murgia Timone viewpoint at 10pm, when the cave city is illuminated by its street lighting and the cave windows glow — the most extraordinary urban nightscape in Italy. Free, 15-minute drive from Matera center. (7) The Carnevale di Ivrea (Ivrea, Piedmont — January/February): the most violent carnival in Italy — the Battle of the Oranges (in which the entire town divides into teams and throws oranges at each other from carts and on foot for 3 days) commemorates a specific medieval rebellion against the local tyrant. 900,000 oranges are thrown annually. (8) The Cetara colatura di alici (Cetara, Campania): the oldest liquid fish sauce in continuous production in Europe — the colatura (the amber liquid pressed from anchovies salted in wooden barrels for 3-4 years, the direct descendant of the Roman garum) is produced only in Cetara (a village on the Amalfi Coast road between Salerno and Amalfi) and available directly from the Delfino store (Via Umberto I 39, €12-18 per 100ml bottle). (9) The Lago di Pilato (Sibillini Mountains, Marche/Umbria — 2-hour hike from Forca di Presta): the only naturally occurring lake in the central Apennines (2,270m altitude, surrounded by snow until July, inhabited by Chirocephalus marchesonii — a small crustacean found nowhere else in the world) — and according to medieval legend, where Pontius Pilate's body was thrown into the water, which is why the lake turns red at certain times of year (actually the Chirocephalus, which reddens in mating season). (10) The Notte delle Lanterne (Opi, Abruzzo — August): the Opi mountain village in the Gran Sasso National Park illuminates the entire medieval center with oil lanterns for one August evening — the oldest light festival in Italy (documented since the 17th century) and the most atmospheric mountain village event in the Apennines. (11) The Santuario di Oropa (Biella, Piedmont): the most visited Marian sanctuary in northern Italy — a complex of 19th-century Baroque basilica, medieval sanctuary, and Alpine landscape at 1,159m altitude in the Biella Prealps; the specific atmosphere of a high-altitude pilgrimage destination where Italian Alpine religious culture is most concentratedly visible. (12) The Stromboli volcano night cruise (Stromboli, Aeolian Islands): observing Stromboli's 15-minute eruption cycle from the sea at 10pm — lava bombs arcing over the crater visible from the boat. €30-40 from Stromboli port.
Twelve travel mistakes in Italy with specific solutions: (1) Booking hotels in the historic center of Florence in August: August in Florence is 38-40°C, very crowded, many restaurants closed (the Florentines leave for the coast). Stay in May-June or September-October. If you must go in August, book accommodation with air conditioning (not guaranteed in medieval palazzi — specifically ask) and schedule museums for morning. (2) Assuming Trenitalia is the only train option: Italo operates the high-speed network on the same routes (Milan-Florence-Rome-Naples) at comparable prices, often cheaper for advance booking. Check both ntv.it (Italo) and trenitalia.com before buying. (3) Renting a car for Rome, Florence, and Venice: cars are a liability in all three city centers — the ZTL (restricted traffic zones) fine will arrive 6-8 weeks later to your home address through the rental company's €40-80 administration fee plus the fine itself. Rent a car only for the rural Tuscany-Umbria-Basilicata portions of your trip. (4) Buying water from tourist restaurants near monuments: a 500ml water bottle at the Vatican costs €3-4. The same bottle at a supermarket (Conad, Carrefour, Esselunga) costs €0.20-0.30. Italy's tap water is excellent everywhere except parts of Sicily and some southern Italian rural systems. (5) Queuing for the Colosseum without pre-booking: the Colosseum in July-August has a queue of 2-3 hours for same-day tickets. Book on coopculture.it at least 3-7 days ahead; the 8am slot gives the morning light and the smallest crowd. (6) Confusing Chianti with Chianti Classico: the most expensive item on an Italian wine list labeled "Chianti" is not the same as a mid-range Chianti Classico. The Gallo Nero (Black Rooster) on the label is the indicator of the historic zone. (7) Using taxis when Uber Black exists: Uber Black operates in Rome, Milan, and Florence — the same comfort as a taxi, the same regulated price (Uber Black in Italy is not surge-priced and uses the same tariff as official taxis), with the booking confirmation and driver tracking that street hailing doesn't provide. (8) Eating at the restaurant with the English-language photo menu nearest the attraction: the proximity to monuments is perfectly correlated with price and inversely correlated with quality. Walk 10 minutes in any direction from the Colosseum/Piazza Navona/Duomo and prices drop by 40%; walk 15 minutes and you find the neighborhood restaurants where Romans/Florentines/Venetians actually eat. (9) Visiting Pompeii without water in July-August: the Pompeii site has minimal shade; the temperature on the basalt streets at midday in August is genuinely dangerous. Visit at 9am (the site opens at 9am; crowds arrive at 11am), carry 1.5 liters of water, wear a sun hat. (10) Thinking Venice is expensive for accommodation: Venice proper (the island) has accommodation at every price point, including well-run hostels (the Generator Venice on Giudecca, the Anda Venice — both accessible by vaporetto). The mainland (Mestre, 10 minutes by train) has hotel prices 50% lower. (11) Not validating train tickets on regional services: Trenitalia regional train tickets (the non-AV services that don't have a specific seat booking) must be validated in the platform machines before boarding — a €50 fine if the ticket inspector finds an unvalidated ticket, regardless of having paid. (12) Assuming Italian restaurants open for lunch from 12pm: most serious Italian restaurants open for lunch from 12:30pm and stop seating at 2:30pm; dinner from 7:30pm (not 6pm). Arriving at 6:30pm to "eat early" will find the restaurant closed. The few restaurants open at 6pm are serving tourists, not Italians.
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