Italy

Top Tip- Do not Request a Milky coffee after 11am

Italy, where the plan is always “just a quick coffee” and three hours later you’re still at the same table arguing about whether the pasta was better in Naples or Bologna (it was Naples, fight me).

It’s the country that ruins other countries for you. You go for the Colosseum and leave planning your entire personality around a spritz habit and unsolicited opinions on olive oil. The regions barely agree with each other, let alone with you, on what “authentic” even means. Rome is chaos dressed up as history, Florence is a Renaissance flex, the Amalfi Coast will bankrupt you scenically, and somewhere in the south you’ll eat a tomato so good you’ll get quietly angry about every tomato you’ve eaten before it.

It’s not a relaxing trip. It’s a lot of walking, a lot of standing in queues you didn’t plan for, and a lot of realising your 9-5 brain doesn’t know what to do with an afternoon that has no schedule because everything’s shut for riposo. But that’s kind of the point. Italy doesn’t perform for you. You just have to show up, eat, walk it off, and let it happen.

Annual events and festivals

• Carnevale (Jan–Feb) — runs from late January into mid-February, (Our Italian Journey) Venice is the big one with masks and costume balls, but Viareggio and Ivrea do their own weird, brilliant versions (Ivrea literally throws oranges at each other, don’t ask, just go).
• Sanremo Music Festival (Feb) — Italy’s biggest TV event of the year, decides who goes to Eurovision. Not one for visitors really, but it dominates the country for a week.
• Easter / Holy Week (Mar–Apr) — proper processions everywhere, Sicily especially goes all in.
• coppio del Carro, Florence (Easter Sunday) — they literally explode a cart in the piazza. Won’t make sense until you see it.
• Festa della Repubblica (2 June) — commemorates the 1946 referendum when Italians voted to abolish the monarchy, with a big military parade in Rome.  (Odynovo Tours)
• Palio di Siena (2 July, again in August) — bareback horse race round the main square, chaos, tradition, absolutely worth building a trip around.
• Umbria Jazz (July) — Perugia turns into one long open-air gig.
• Ferragosto (15 Aug) — the entire country stops. Shops shut, cities empty, everyone’s at the beach. Do not try to run errands this week.
• Venice Film Festival (late Aug–early Sept) — the celebrity circus one.
• Alba White Truffle Fair (Oct–Nov) — Piedmont, if you’re a food person this is basically a pilgrimage.
• Christmas markets (Dec) — every town gets one, but Bolzano and Trento (South Tyrol) do it properly, more Alpine than Italian.