Book the first night luxury. Always.
This is not a lifestyle upgrade. It's a strategic decision. Arriving tired into a great hotel resets everything — a good bed, a functioning shower, a room that doesn't require mental energy to tolerate. Arriving tired into a bad one ruins the first day, which colours the second, which is most of the trip.
The first night is the most expensive night to get wrong. Budget accordingly. The remaining nights can be wherever you want.
The logic: You're at your lowest point physiologically — jet lag, transit exhaustion, decision fatigue. The hotel carries you. Make sure it can.
One non-negotiable
reservation per day.
Overplanning kills spontaneity. Underplanning kills the experiences worth having. The middle path: one unmissable dinner, museum, or hour in a particular neighbourhood booked in advance. Let the rest of the day breathe around it.
The reservation becomes the spine of the day. Everything else hangs off it naturally — where to have lunch nearby, what to do in the hours before, where to end up after. Structure creates freedom rather than constraining it.
In practice: The restaurant you really want is booked six weeks out in most cities worth visiting. Plan the dinner first. Build the day from there.
Eat where the receipt is in the local language.
Not a rule about avoiding tourists — it's a rule about proximity to the source. When a restaurant prints its receipts, menus, and specials in the language of the city you're in, it's almost always because its primary relationship is with the people who live there. That relationship produces better food.
Ambrosia Bistro in Santiago — one of the best meals we've had in South America — has a receipt entirely in Spanish. The waiter was named Claudio. Nobody spoke English at the table next to us. Correct.
Corollary: If the menu has photographs and is available in six languages, keep walking.
The 11am problem.
Nobody tells you about this. You've landed, checked in early on pure luck, and it's not yet lunchtime in a city you've never visited. This is the most important hour of any trip. What you do with it sets the tone for everything that follows.
The answer is always the same: walk. Not towards anything in particular. Just into the nearest neighbourhood that seems to have people in it. Buy a coffee from somewhere without a logo. Sit. Watch. Let the city explain itself to you before you start imposing an itinerary on it.
What not to do: Check into the hotel room, lie down "just for a moment," and wake up at 4pm. You know who you are.
Pack one fewer thing than you think you need.
This applies to clothes, shoes, and plans. The thing you leave behind is almost never the thing you needed. The thing you took up space with is almost always the thing you didn't use. Every experienced traveller arrives at the same conclusion eventually: the bag gets smaller, the trips get better.
The exception is medication, adapters, and anything that cannot be purchased at a pharmacy in the destination city. Pack those twice.
The test: Before zipping the bag, remove the last thing you added. If the trip survives, it didn't need to come.
Know what kind of trip
you're actually on.
There are broadly two modes: the trip where you do things, and the trip where you stop doing things. Both are legitimate. The mistake is arriving on a rest trip with a doing-things itinerary, or vice versa. Decide before you land which one you need, and plan accordingly.
The professional traveller — the one who flies constantly for work, who moves between hotels like a commuter, who has a loyalty number for everything — almost always needs the second kind of trip and books the first kind out of habit. Stop. You know what you need.
How to tell: If the first thing you're looking forward to is the hotel bed, you're on a rest trip. Book the spa. Cancel two things on the itinerary. No regrets.