A Private Journey to Italy

The warmest city on the trip. We arrive in the afternoon and have just one full morning before the train north — comfortable walking weather, crisp evenings. A light-to-medium coat is all you need. Rain is possible but usually brief.

The longest stay and the one that demands the most preparation. November is Florence's rainiest month — expect some wet days across the five nights here, including the Lucca and Siena day trips. Evenings are genuinely cold. Layers are essential, and footwear matters most here — wet cobblestones are slippery.

The coldest leg, particularly the Langhe day trip — open hilltop vineyard country with wind. Pack your warmest layer for this. The good news: Turin's famous arcaded streets mean you can walk for miles without getting rained on.

Shoes

The Most Important Decision

Rome, Florence, and Turin are all cobblestone cities. Wet November cobblestones are slippery. This is not the trip for cute-but-painful shoes. Bring waterproof leather boots or sturdy leather-look walking shoes that you've already broken in. Not athletic sneakers — leather or leather-look is both more comfortable on uneven stone and far more appropriate. One pair of comfortable, worn-in shoes will serve every day and every dinner on this trip.

Clothing

Pack for layers, not bulk. You need: one good coat, 2–3 sweaters or long-sleeve tops, dark jeans or smart trousers, a couple of simple day tops, one slightly nicer top for the truffle lunch in Alba (the one occasion that earns it — everything else is casual). That's genuinely all you need. Resist the urge to overpack; train travel rewards a well-packed bag and cobblestones punish a heavy one.

Rain Gear

A compact folding umbrella or a packable rain jacket — not a poncho. November rain in Italy tends to come in bursts; you want something you can slip in a bag, not something you have to carry all day.

Day Bag

A crossbody bag rather than a backpack. It's more comfortable for all-day walking, keeps your belongings at your side rather than behind you, and reads as local rather than tourist. Bonus: far harder to pickpocket in crowded areas like the Vatican or Campo de' Fiori.

Scarf

A good scarf does triple duty on this trip: warmth in Turin and Florence evenings, a shoulder cover for churches (Vatican rules, see below), and it's the single easiest way to look Italian. A light wool or cashmere scarf in a neutral color is worth every inch of packing space.

Extras & Tech

You'll need a Type L power adapter for Italy (the one with three prongs in a line). A portable phone charger is also highly recommended since we'll be using our phones for photos and maps all day. And as mentioned, a small, secure crossbody day bag is essential for everyday carrying.