Route Notes

Five cities, seven days: yes, it's possible — here's the math

Everyone says it can't be done without spending the whole week on a train. Everyone is routing it wrong.

There's a version of this trip that's miserable. You've seen it: a different hotel every night, a suitcase that never fully unpacks, a blur of train stations that all start to look the same. That version is real, and it's why every travel blog tells you to "slow down and pick two cities."

Here's what they don't tell you: the misery isn't caused by the number of cities. It's caused by the routing. Five cities in seven days is completely doable — delightful, even — if you respect three rules that almost nobody follows.

Rule one: sleep in hubs, day-trip the spokes

The amateur version of this trip checks into five hotels. The charted version checks into two. Pick your two anchor cities — the ones with the best rail connections, not necessarily the most famous ones — and let the other three be day trips. You keep your room, your suitcase stays unpacked, and you still wake up somewhere new in spirit every morning.

"You don't need five hotels to see five cities. You need two good beds and a rail map read correctly."

Rule two: travel at the hours nobody wants

The 7:05 a.m. train feels like a punishment when you book it. It feels like a cheat code when you're standing in a piazza at 9:30 with the whole day ahead of you and the tour groups still at breakfast. One early train per trip — placed correctly, ideally mid-trip when your body clock has adjusted — buys you an entire extra day. We'll tell you exactly which morning to spend it on.

Rule three: the second-to-last day is sacred

Every itinerary we chart leaves the second-to-last day almost empty. Not the last day — the one before it. That's the day you go back to the neighborhood you loved, buy the thing you talked yourself out of, and sit with a coffee doing absolutely nothing. It's the day the trip stops being a checklist and becomes yours. Schedule it and the whole week breathes.

The worked example

Here's a real seven-day frame we've charted more than once: anchor in Florence (nights 1–4) with day trips to Bologna and Siena — both under 90 minutes door to door — then one early train to anchor in Rome (nights 5–7). Five cities. Two hotels. One early alarm. Nobody cries at a train station.

The same skeleton works in Japan (Tokyo + Kyoto, day-tripping Nara, Osaka, and Hakone), in Iberia (Madrid + Lisbon), and in a half-dozen other places we're happy to argue about over an intake call.

Want this routed for your dates, your pace, and your appetite? That's the job. Begin a trip and tell us the half-formed version of the dream — we'll do the math.