Siena

Prioritise Oltrarno, Fiesole and Chianti Classico. What you can skip without regret: the restaurants with photo menus and touts on the main square, any hop-on bus if the centre is walkable, and paid "panoramic" viewpoints when a free one gives the same picture. Siena is inland, so plan around heritage, food and landscape rather than beaches.

Stay inside or immediately beside the historic centre of Siena: you walk to the main sights, restaurants stay open late nearby, and you avoid paying for taxis twice a day. Pick the edge of the old town if you want quiet at night, and check the room faces a courtyard rather than a bar street.

Walk everywhere in the centre; regional trains reach Pisa, Siena and Arezzo in about an hour. As a rule: take the scheduled bus or train for the cheapest ride, an official taxi rank or a ride-hailing app when you land late or carry luggage, and never accept a lift from someone approaching you inside the terminal.

2 full days is the honest answer for Siena: one for the centre on foot, one for its museums and food, and one for a trip into Florence, Italy. Two days works if you only want the highlights; a fourth day is worth it if you want a slow morning and a longer excursion.

Budget €110–160 per person per day mid-range: €35–50 food, €10 transport, €25–40 museums and sites. Accommodation moves the total most: shoulder season in Siena can be half the July price for the same room. Payment runs on the euro (carry €20–30 cash for small bars and markets).

Day 1 — the historic core of Siena on foot, clockwise from the main square, with lunch where you end up rather than walking back. Day 2 — the single biggest sight first thing, then the market and the residential streets around it, and a viewpoint at sunset. Day 3 — one excursion into Florence, Italy booked in advance, back for a late dinner. Group everything by walking distance and never cross Siena twice in a day.

Anything with timed entry or a small group sells out first: the flagship monument or museum of Siena, guided tours with fewer than fifteen places, boat and wine experiences in summer, and dinner at well-reviewed restaurants on Friday and Saturday. Book those two to four weeks ahead in high season; everything else can wait until you arrive.

The classics are the same everywhere: unmetered taxis quoting a flat fare, "free" bracelets or flowers, distraction pickpocketing on crowded transport and at photo spots, card machines handed over pre-set to a higher amount or to your home currency, and restaurants without printed prices. Check the meter, always pay in euros, and keep your bag in front of you in queues.

In Italy, no percentage tipping — expect a coperto of €2–4 per person on the bill; rounding up is enough. Lunch 12:30–14:30, dinner 19:30–22:00; coffee is drunk standing at the bar and costs less that way. Cover shoulders and knees inside churches, greet staff before ordering, keep your voice down in residential streets at night, and expect shops in smaller towns around Siena to close in the early afternoon.

Install Google Maps, Trenitalia and Italo for trains, ATM/Moovit for city transport, TheFork for bookings, IO for museum passes. Download an offline map of Siena before you land, and add your transport card or pass to your phone wallet if the local operator supports it.

Walk two or three streets off the main square or monument in Siena and look for a short handwritten menu, a full room of local voices, and prices displayed at the door. A daily menu chalked up at lunchtime is the strongest signal; a laminated menu in five languages with a host outside is the strongest warning.

Eat what Florence, Italy grows and lands: the signature rice, stew or grill of the region, whatever the market is selling that week, and the local wine or vermouth by the glass. The most honest versions are in the family-run place near the market of Siena, at lunch, when the daily menu is on.

Lunch 12:30–14:30, dinner 19:30–22:00; coffee is drunk standing at the bar and costs less that way. Book dinner for anything popular, ask for the bill (it won't arrive unprompted), and split payment is usually fine by card. No percentage tipping — expect a coperto of €2–4 per person on the bill; rounding up is enough.

Do a single loop of the historic centre of Siena, stop at its one defining sight, then eat where locals eat near the market. That gives you the character of the place in three or four hours without a ticket queue eating the whole visit.

Free: the highest point of the old town, the bell tower terrace when it's open, and the bridge or promenade that looks back at Siena's skyline. Paid: a rooftop bar or tower ticket — worth it only if you arrive forty minutes before sunset to get the rail. Inland, the ridge or castle road above town gives the widest light.

validate every ticket before boarding; day passes pay off from three rides, and regional trains are cheaper than the high-speed ones If your 2-day plan is mostly on foot in Siena with one excursion, buy singles or a multi-journey card and skip the tourist pass; if you're crossing the city several times a day or using it with museum entry included, a 48 h pass pays for itself.

Siena is safe by European standards; the real risks are opportunistic. Avoid empty industrial or station peripheries after midnight, unlit parks, and packed nightlife streets where phones disappear. Walk lit main streets, use a licensed taxi or ride-hailing app late at night, and share your route if you're travelling solo.

Buy something made nearby: estate olive oil, a Deruta or Vietri ceramic, artisan pasta, a leather notebook from a workshop rather than a stall. The weekly market in Siena and a workshop with the maker on site beat any airport shop, and you're supporting the local trade rather than an importer.

Keep two indoor blocks in reserve: the main museum or cathedral of Siena, a market hall with food stalls, a long lunch, or a thermal bath or wine cellar in Florence, Italy. In extreme heat, invert the day — sights before 11:00, indoors from 14:00 to 18:00, and the evening back outside. April–June and September–October; July and August are hot and crowded.

Locals go where there's no ticket desk: the residential lanes just outside the walls of Siena early in the morning, the neighbourhood bar with four tables and one dish, the cemetery or convent garden that nobody photographs, and the hill road out of town at dusk. Ask the person serving you coffee where they eat on Sunday — in Florence, Italy that question opens more doors than any list.