Siena

Exit the fortress south through La Lizza park and drop down Via della Sapienza — 7 minutes of shaded plane trees and a steady descent into the historic core. This austere Dominican brick basilica (begun 1226) sits on the hill opposite the Duomo, which is precisely why every Siena postcard is shot from its rear terrace: the cathedral appears across the valley exactly framed between two medieval rooftops, with nothing modern in view. Saint Catherine of Siena preached here; her head relic is inside (we stay outside today).

Tip: Walk around to the eastern terrace behind the church — this is the iconic Duomo-across-the-valley viewpoint. The cathedral's striped facade is lit head-on until roughly 12:00, after which it falls into shadow, so time the shot before noon. A low stone wall makes the perfect tripod.

Continue southeast down Via del Capitano — a 10-minute walk through narrow medieval lanes hung with the painted flags of Siena's 17 contradas. The Duomo is Italy's most theatrically decorated cathedral: alternating white-and-black marble stripes, a rose-window facade encrusted with gold mosaics and carved prophets, and a compact piazza that forces you right up against the detail. Circle around behind to the Facciatone — the massive unfinished wall of a 14th-century expansion the Black Death ended forever, its empty pointed arches now a dramatic sky frame.

Tip: For the postcard shot, cross to the stone steps of Santa Maria della Scala directly opposite the facade — you capture the full zebra-striped campanile, rose window and marble saints in a single frame. Best between 11:30 and 13:00 when the sun is frontal; by 14:00 the facade is half in shadow.

Duck east from the Duomo down the tight Costa dei Barbieri stairway — 5 minutes and you pop out into Piazza del Mercato, the old market square tucked directly behind Campo. This is a single-room family deli where Gino himself slices your panino behind a marble counter stacked with local pecorino di Pienza, cinta senese prosciutto, and jars of house-pickled artichokes. There are no tables — you eat standing at the counter or carry it to the wooden benches on the terrace overlooking the valley. Try the Finocchiona e Pecorino panino (€8) with wild-fennel salami, or the Cinghiale with wild boar salami and truffle cream (€9). Budget €10-15 with a glass of Chianti.

Tip: Arrive by 13:15 — after 13:30 the queue snakes out the door and Gino stops taking new orders by 14:30 sharp. Tell him 'quello che consigli oggi' (whatever you recommend today) and he'll cut you something off the menu, usually a salty fossa cheese aged in underground pits.

Climb the 80-meter Vicolo di San Pietro alley back up from the market — two minutes and you emerge onto the sloping red-brick shell that is the most beautiful square in Italy. The Campo is divided into nine segments radiating down to the Palazzo Pubblico and the 102-meter Torre del Mangia, and twice a year (July 2, August 16) this is the track where the bareback Palio thunders around the edge. Walk the full perimeter, then break away up Via Banchi di Sopra to Piazza Salimbeni (home of Monte dei Paschi, the world's oldest operating bank, founded 1472), loop back down the medieval palazzi of Via di Città, and finish by sitting on the warm bricks at the center of the shell as the light shifts.

Tip: From about 16:30 the sun hits the Palazzo Pubblico facade head-on and the brick goes molten orange — this is the golden moment. Sit on the pavement at the bottom of the shell like locals do (nobody stops you) rather than on the café terraces lining the square, where Bar Fonte Gaia and its neighbors charge €6 for an espresso. Walk 50 meters into any side street for the same coffee at €1.50.

Leave the Campo through the arch at Via del Porrione on the east side — 90 seconds, and Le Logge sits under a marble portico on the left. Siena's defining trattoria since 1880, housed in a 13th-century pharmacy with the original dark-wood apothecary cabinets still lining the walls floor to ceiling. The owner, Gianni Stoppini, also runs a wine estate in Montalcino, so the Brunello list is serious business. This is where you order pici — the thick, hand-rolled Tuscan spaghetti that essentially doesn't exist outside this region. Try the Pici al Ragù di Cinta Senese (€19) with heritage-breed Tuscan pork slow-cooked 6 hours, and the Tagliata di Chianina (€32) seared on rocket with shaved pecorino. A glass of their own Sangiovese runs €9. Budget €55-75 with wine.

Tip: Reserve 48 hours ahead by phone or email — Le Logge is full every evening and walk-ins are turned away by 19:45. Ask specifically for the sala interna (inner room) so you sit among the historic pharmacy cabinets, not at the outdoor tables. Pitfall warning for the Campo area: ignore any restaurant on Via di Città or the Campo perimeter that posts photos of food, offers an English-only menu, or has a host on the street calling you in — those are the classic Siena tourist traps serving pre-frozen pasta at double the price. If locals aren't eating there on a weekday, keep walking.

Come down from the tower and walk 40 meters across the same courtyard — the museum entrance is on the ground floor of the Palazzo Pubblico, the building you just climbed. This is where Ambrogio Lorenzetti painted the Allegory of Good and Bad Government in 1338, the first great secular fresco cycle in European art, and where Simone Martini's Maestà watches over the Sala del Mappamondo. Morning is essential — the Lorenzetti hall faces west, so by afternoon the frescoes glare under reflected light and tour groups fill the narrow room shoulder to shoulder.

Tip: Buy the combined Mangia + Civico ticket (€20) at the booth before you climb — it saves €5 and a second queue. Skip the audio guide and go straight to the Sala della Pace; stand in front of the Effects of Good Government on the City wall — that mule caravan on the right is the world's first painted traffic jam.

Exit the Palazzo Pubblico through the back arch into Piazza del Mercato — the salumeria is 80 meters along the arcade on your left, under a faded sign painted in 1948. Gino's family cures their own finocchiona (fennel salami) and carves prosciutto di cinta senese from the black Tuscan pig; ask for the panino misto (€7) and the tagliere piccolo with pecorino di Pienza and a glass of Chianti Colli Senesi (€12). You eat standing at the marble counter or perched on the outdoor bench looking over the Valdimontone countryside that falls away behind the Palazzo.

Tip: Gino himself is there most mornings — ask for a taste of the cinta senese before ordering, he will cut you a sliver for free. The pecorino stagionato in fossa is the one locals buy by the kilo; the 'young' pecorino on most tourist menus is not the real thing.

From Piazza del Mercato take Via di Salicotto north, cut through Via Banchi di Sopra and bear left down Via della Sapienza — 15 minutes of walking through Siena's quietest medieval alleys, past the University and a sudden view of the Duomo across the ravine. The brick basilica sits on a promontory like a fortress; inside, in the Cappella di Santa Caterina, is the preserved head of Saint Catherine of Siena, patron saint of Italy, displayed in a gilded reliquary alongside a thumb from her right hand. Afternoon light falls through the high rose window and turns the bare brick walls the color of Sienese earth — the Dominicans designed it this way, austere on purpose.

Tip: The Sodoma frescoes of Catherine's ecstasy are to the right of the altar — a coin-operated light switch (€0.50) on the pillar illuminates them; without it you will miss the faces entirely. Exit through the side door facing the Duomo for the single best photograph of the cathedral in Siena, framed between two cypresses.

Walk back down Via di Camporegio and Via Banchi di Sopra — 12 minutes, all downhill, and the Campo suddenly opens below you through the Croce del Travaglio. This is the hour Sienese call 'l'ora del Campo' — the sun drops behind the Torre del Mangia, the nine wedges of pink brick glow like embers, and residents lie down on the sloping pavement with a bottle of wine. Sit at the lowest point of the shell with your back to the Fonte Gaia, look up, and understand why this square is considered the most beautiful in Italy — the whole medieval republic designed it to pull your body toward the Palazzo Pubblico, the seat of the people.

Tip: The Fonte Gaia fountain you see is a 19th-century copy — Jacopo della Quercia's original panels are inside Santa Maria della Scala (tomorrow). Do not sit at a café table on the Campo — a coffee costs €8 and a €2 cover per person; locals buy a bottle from the enoteca on Via di Città and drink on the pavement, which is legal and free.

Leave the Campo through the arch next to the Torre and turn right into Via del Porrione — 90 seconds of walking. This is Gianni Brunelli's 1880 pharmacy turned osteria, still with the original walnut cabinets and apothecary jars, now serving the Brunelli family's own wine from their Montalcino estate. Order the pici cacio e pepe al tartufo (€22) — hand-rolled fat spaghetti rubbed with pecorino, black pepper and shaved summer truffle — and the peposo alla fornacina (€26), a slow-cooked beef stew of Chianti, black peppercorns and garlic that Brunelleschi's workers invented to eat beside the kiln. Budget €55–70 with a glass of the house Rosso di Montalcino.

Tip: Reserve at least two days ahead (+39 0577 48013) and ask explicitly for the ground-floor room — upstairs is a newer annex without the original wood. Around the Campo, any restaurant with a multilingual photo menu on an easel is a tourist trap charging €18 for a caprese; the giveaway is a waiter standing outside waving you in.