Eight questions to ask before you book your next trip: breath, walking, water, focus, the view, sleep, company and one unbooked afternoon, each with one book to read first.
A note before the books. Where a title is linked, the link goes to an independent bookshop, and some of these links may earn Orophile Edit a small share if you buy there. No publisher or bookshop chose these titles, and none paid to be here.
Alain de Botton opens The Art of Travel with a man who never leaves. Des Esseintes, the hero of Huysmans's novel Against Nature, sets out for London after reading Dickens. He gets as far as Paris, buys a guidebook, eats an English dinner in an English tavern while he waits for the train, and decides the trip in his head is good enough. He goes home and never travels again. De Botton then goes to Barbados himself and finds the opposite problem: he arrived, but he had brought himself along, tired body and restless mind included.
That second problem is the one most itineraries are built to ignore. They are planned for the place, and the person is fitted in around the transfers. In thirty years inside hotels, I watched a great many people arrive on holiday still moving at the speed of the airport.
I recently sat in on a session about small daily resets: breathe, move, drink water, rest your eyes, sleep, talk to someone. None of it was new, and that was the point. These are the first things a travel plan squeezes out. So I turned them into eight questions to ask before you book. They are not rules. They are a way to check whether the days you are planning will leave you rested, or only busy. Each one comes with a book to read the night before you decide.
Does the itinerary leave room to pause, settle in, and enjoy where I am?
The first day of most trips goes on getting there, and the second goes on catching up with the first. Look at the arrival day. If it ends with a dinner reservation and starts the next morning with a seven o'clock pickup, you have planned a relay, not a rest. Half a day with nothing in it is the cheapest thing you can add to any trip.
James Nestor, Breath: The New Science of a Lost Art. A journalist who, as an experiment, spent ten days breathing only through his mouth, then set about learning to breathe well again. Read it for the practice, which is simple: slower, and through the nose. Some of its science runs ahead of the evidence. The practice does not need it to.
Are there comfortable opportunities to walk, stretch, or explore at my own pace?
Count the seated hours in the plan: coach, table, transfer, table again. Then find the walk. Walking is the one kind of exercise nobody on holiday has to be talked into, as long as the day leaves room for it. The question that matters is whose pace it is: yours, or the group's.
Frédéric Gros, A Philosophy of Walking (translated by John Howe). The book that taught me the walk is where the thinking happens, not a break from it. The rest of that shelf, and the trail guides, are in Books for the Walk.
Will drinking water be readily available during transfers and excursions?
A plain question, and the one I see missed most often. Long transfers, dry hotel air, heat and altitude all take water from you faster than you notice, and a flat afternoon is sometimes nothing more than thirst. Ask what is on the coach, what is at the trailhead, and whether the day's stop has a tap you would drink from.
Wallace J. Nichols, Blue Mind. Water to drink is logistics. Water to be near is something else. Nichols, a marine biologist, gathers the research on why people settle beside rivers, lakes and the sea. The evidence is suggestive rather than settled, so read it as an argument for choosing the room with water outside the window. For the colder version, see Cold Water Is Not a Dare.
What is the one moment I most want to be present for each day?
An itinerary with six highlights a day has none. Choose one thing each day that you would be sorry to have half-watched: a morning on the water, a long lunch, the last hour of light on a ridge. Protect that, and let the rest be optional.
Oliver Burkeman, Four Thousand Weeks: Time Management for Mortals. The title is the arithmetic of an ordinary life: about four thousand weeks, if you are lucky enough to reach eighty. Burkeman's argument is that you will never get through everything, so the useful skill is choosing. It is the best book I know for anyone in a second chapter who has stopped pretending there is time for all of it.
Where can I put my phone away and enjoy the landscape around me?
Unplugging has limits, which I wrote about in Digital Detox, Read Honestly. A view that is better than the screen has none. Before you book, find the places in the plan where the landscape does the work: a terrace, a path, a window seat on the slow train. That is where the phone goes back in the bag without an argument.
Florence Williams, The Nature Fix: Why Nature Makes Us Happier, Healthier, and More Creative. A journalist goes looking for the research on what time outdoors does to attention and mood, from forest-walking studies in Japan to Finland. It pairs well with The Forest Is Not a Backdrop.
Have I allowed enough time for sleep, especially after a long journey?
The night after a long flight is not really a night. It is a debt, and the morning after is when it is collected. Book nothing early on the first full day. If the flight lands late, move the first excursion, not your sleep.
Alex Soojung-Kim Pang, Rest: Why You Get More Done When You Work Less. Pang looks at how Darwin, Dickens and others did their best work in a few focused hours a day and spent the rest walking, napping and sleeping. In his account, rest is a skill to practise rather than a reward you earn.
Is there space for a meaningful conversation, a shared meal, or time with someone I love?
Travelling with someone you love can turn into a set of logistics you manage together. Leave one meal a day unplanned: no booking, no view to chase, just the table and the conversation you came for.
If the same quarrel comes back on every trip, it is usually not about the plan. Some travellers want the day full of people, some want every hour mapped, some want to lead, some want to sit still, and two people who love each other are rarely the same kind. Florence Littauer sorted those four into the old temperaments in Personality Plus (1983): sanguine, melancholic, choleric, phlegmatic. Read it as a lens, not as science. The four types come from ancient medicine rather than research, and nobody is only one of them. Used lightly, it turns an argument about the itinerary into a conversation about pace, and that conversation is better had before you book than on the second morning.
Robert Waldinger and Marc Schulz, The Good Life: Lessons from the World's Longest Scientific Study of Happiness. The authors lead the Harvard Study of Adult Development, which has followed the same people since 1938, and now their children. Its clearest finding is a plain one: the quality of people's relationships tracked their health and happiness in later life more closely than money or fame did. It does not promise anyone a longer life, and neither does this journal. It does suggest who to sit with at dinner.
Can I enjoy an afternoon without a reservation or a deadline?
A trip that is fully booked has already happened on paper. The unbooked afternoon is where it can still surprise you: the side street, the second coffee, the bench you did not plan to sit on. Put one in the plan on purpose, and defend it.
Carl Honoré, In Praise of Slow. The Canadian journalist's account of the slow movement, from food to work to cities. Twenty years on, it reads less like a trend piece and more like common sense that most of us still do not follow.
When you have been through the eight, finish the sentence:
On this journey, I would like more ______ and less ______.
One habit I would like to bring home: ______.
Keep your answer beside you as you plan. The last line is the one that matters after the flight home. A trip that rests you for a week is pleasant. One that sends a single habit home with you is worth more.
Des Esseintes decided the trip in his head was enough. These questions are for the other kind of traveller: the one who is going, and would like to arrive.