Tuscany Italy

Tuscany Beyond the Cliches

Tuscany has been sold so many times on olive oil bottles and wine labels that first-time visitors sometimes arrive expecting a film set. The rolling hills of the Val d’Orcia really do look like that. The cypress lines, the stone farmhouses, the October light - it is all accurate. What the posters omit is that August is extremely hot and overcrowded, that parking in Florence requires advance booking, and that the most interesting eating is in towns that most tour groups skip entirely.

Florence and the crowds

Florence is worth a week. Most people give it two days, which means they queue for the Uffizi for two hours and leave. Book the Galleria dell’Accademia (David) and the Uffizi at least three weeks ahead online; you pick a timed entry slot and avoid the worst of it. The Bargello sculpture museum on Via del Proconsolo is consistently undervisited and has Donatello’s bronze David - arguably more interesting than Michelangelo’s - with no wait.

The Oltrarno neighbourhood on the south side of the Arno is calmer and has better lunch options. Trattoria Sostanza on Via del Porcellana does a butter-fried artichoke pasta (EUR 14-18) that has not changed in 150 years. The Brancacci Chapel with Masaccio’s frescoes is 10 minutes from there and rarely busy before 10:00.

Siena and San Gimignano

Siena’s Piazza del Campo is genuinely extraordinary - the scalloped brick square surrounded by medieval palazzi is one of the few places in Italy that lives up to hype. Skip the Cathedral’s Piccolomini Library if time is short (pleasant but minor); the civic Palazzo Pubblico with its Lorenzetti frescoes of Good and Bad Government is the more revealing choice. Siena rewards an overnight; the daytrip crowd leaves by 17:00 and the city is a different place after that.

San Gimignano is pretty but has become a tourist market with a medieval backdrop. Go at 08:30 before the coaches arrive, get the gelato at Gelateria Dondoli on the main square (multiple world championship wins, not marketing), and leave by noon.

Eating the region properly

A Florentine steak (bistecca alla Fiorentina) should be at least 1kg and cut from Chianina beef. Order it blue - that is the correct preparation, not rare. At Buca Mario on Piazza Ottaviani, expect EUR 45-55 per kilo. Do not order it well-done; the waiter will say something about it.

Outside Florence, the food improves and the prices drop. In Montalcino, Enoteca Osticcio pours Brunello by the glass from around EUR 12 and serves cured meats from the Maremma for EUR 10-15. In Pienza, the pecorino cheese sold in the Via del Casello shops is legally protected - the sheep graze in the Val d’Orcia specifically to produce it.

Driving the countryside

Renting a car for two to three days and driving the SP146 between Pienza and San Quirico d’Orcia gives you the cypress-lined views without any real planning. The road is slow and the villages it connects - Bagno Vignoni with its central thermal pool, Montalcino above its valley - are all worth stopping for. Fill the tank before leaving any town; rural petrol stations keep erratic hours.

When to go

Late September to mid-October: the vendemmia (grape harvest) is underway, accommodation prices have dropped from August peaks, and the light is the best of the year. April is also good for the hillside wildflowers. July and August are fine if you book everything in advance and accept the heat. December through February is quiet but cold, and many agriturismos outside the main towns close entirely.