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Santorini stays worth the splurge.
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Dubai's most jaw-dropping hotels.
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Cozy luxury with a mountain view.
Hotels, villas, and stays we've actually booked, the views, the value, and whether they're worth it.
Santorini stays worth the splurge.
Dubai's most jaw-dropping hotels.
Cozy luxury with a mountain view.
For a long time I thought of a hotel as a kind of necessary parenthesis, somewhere to set down the bag, shower off the airport, and wait for the real day to begin out in the streets. The room was a base camp, nothing more. Then, somewhere along the way, I began to notice that the places I remembered most vividly were not always the famous sights I had crossed oceans to see. They were the rooms. A particular slant of morning light on a wooden floor. The smell of coffee drifting up a stairwell. A window I kept returning to.
That changed how I travel. I started to understand that where you sleep is not a footnote to a place, it is part of how you take the place in. You are most yourself, most unguarded, in the hours before sleep and the first minutes of waking, and those hours happen inside four walls you chose. Choose them carelessly and they vanish from memory. Choose them with care and they become the frame through which you remember everything else.
So this page is a long thought about that idea: that a stay can be the trip and not merely the place you keep your luggage while the trip happens elsewhere. I am not here to sell you a list of rooms. I am here to talk about what makes a room worth remembering, and how I try to find those rooms, and why I sometimes get it gloriously wrong.
None of this is a formula. Travel resists formulas, which is part of why I love it. But there are habits of attention I have picked up over years of wandering, and I want to hand them to you the way a friend hands you a folded map with a few circles drawn on it, not as instructions, but as suggestions from someone who has been down the road and come back changed.
There is a whole spectrum of places a person can lay their head, and I have come to believe that each kind gives you something the others cannot. The grand hotel, with its high ceilings and its hush, gives you a feeling of occasion, the sense that arriving is itself an event, that you have stepped briefly into a more ceremonious version of your own life. There is nothing wrong with wanting that. Some places are meant to be entered like a cathedral.
At the other end sits the tiny guesthouse, the spare room above a family's kitchen, the cabin with a wood stove and a kettle. These give you something the grand hotel rarely can: proximity. You hear the household waking. You learn what the neighborhood smells like at six in the morning. The host might press a piece of fruit into your hand on the way out and tell you, in broken shared language, which way to walk. That kind of stay does not impress you. It includes you.
Between those poles live a hundred shapes worth knowing, each carrying the character of where it grew up:
I do not rank these. I reach for different ones the way you reach for different clothes, depending on the weather and the mood and the kind of memory I am hoping to make. The mistake is to assume one kind is always the right one. The art is in matching the stay to the trip you actually want.
Here is a distinction I keep coming back to, because I think it quietly explains most of the disappointment people feel about expensive trips. There are two kinds of luxury, and they are not the same thing, though the travel industry works hard to make us believe they are. The first is luxury as price, thread counts, marble, a tap you can summon a person with. It can be wonderful. It can also leave you strangely cold, sitting in a beautiful room feeling nothing in particular.
The second kind is luxury as meaning, and it has almost nothing to do with money. It is a window that frames a mountain so perfectly you keep looking up from your book to check it is still there. It is a host who remembers, on the second morning, that you take your coffee black. It is a silence so complete you can hear the building settle at night. It is a room with a story in its bones, a place that was something else before, that has been loved a long time, that carries the patina of other people's good evenings.
When the two kinds of luxury arrive together, that is a rare and lovely thing, and I will not pretend it isn't. But when I have to choose, I choose meaning every time. I would rather have the small room with the extraordinary view than the large room facing the parking lot. I would rather have the host who treats me like a guest than the staff who treat me like a transaction. Price can buy you comfort. It cannot buy you the feeling of being somewhere that matters, and it is that feeling I am chasing.
If you take one idea from this whole page, let it be this: stop asking how much a stay costs and start asking what it gives. Sometimes those answers line up. Often they do not. The traveler who learns to tell them apart will spend less and remember more.
The easiest mistake in the world is to choose a stay that protects you from the very place you traveled to meet. It happens by accident, usually. You are tired, the familiar chain looks safe, the photos are reassuringly generic, and so you book a room that could be in any city on earth, and then you wonder, a few days in, why the trip feels oddly muffled, like watching a country through tinted glass.
I try to do the opposite now. I look for a stay that belongs to its place, that could not be picked up and set down anywhere else. In a city built of a certain stone, I want walls of that stone. By the sea, I want the windows to open and the salt to get in. In a place where people gather on rooftops in the evening, I want a rooftop. The goal is not roughing it, comfort matters, and I am not ashamed of wanting it. The goal is permeability: a place that lets the location seep in rather than sealing it out.
That said, there is a real and human counter-truth here. Sometimes you genuinely need the sanctuary. After a long stretch of hard travel, or in a place whose intensity has worn you thin, a quiet familiar room can be exactly the mercy you require, and choosing it is wisdom, not failure. The skill is knowing which kind of day you are having, when to open the windows to the world, and when to close them and rest. Both are legitimate. Neither is the right answer for every night.
People sometimes assume that because I love beautiful places to stay, I must always be reaching for the grandest option available. The truth is more interesting and a good deal cheaper. Some of my most treasured nights have cost very little, and a few of my most forgettable ones cost a great deal. What I have learned to do instead of spending evenly is to spend pointedly, to choose, on each trip, the one or two nights that are worth a splurge and let the rest be simple.
The case for sometimes splurging is real. There are places where the stay is the entire point, a remarkable building, a setting so extraordinary that paying to wake up inside it is paying for the memory itself, not the mattress. On those nights I do not flinch at the cost, because I am not really buying a room. I am buying a morning I will describe to people for years. That is a fair trade, and I make it gladly when the place earns it.
But the case for going simple is just as real, and I think it is undersold. A plain room teaches you things. It sends you out into the streets because there is no reason to linger inside. It frees up money for the meal, the train, the extra day you would not otherwise have taken. And it has a way of surprising you, the modest guesthouse run by people who care often holds more warmth than the polished place that does not. The art is the mix: a little grandeur where it counts, plenty of simplicity everywhere else, and the wisdom to know which is which before you book.
When I think back on the stays that have stayed with me, it is almost never the grand gesture I remember. It is the small thing, the detail no brochure would think to mention, the touch that told me a human being had thought about my comfort rather than a checklist. Those details are what separate a place you slept from a place you loved, and the strange part is how little they cost and how rarely they are guaranteed by price.
Here are the small things I have learned to treasure, and to look for:
You cannot always know which of these a stay will have before you arrive, and that uncertainty is part of the romance. But you can learn to read for them, to notice when a description lingers lovingly on a courtyard or a kitchen, and to suspect that lingering is a sign of care. Care is the real amenity. Everything else is furniture.
Choosing a stay from a distance is an act of faith, and the modern traveler performs it through a glass of photographs and reviews that are not always telling the whole truth. I have learned to read these the way you read a person who is being careful with you, paying as much attention to what is left unsaid as to what is stated outright. A listing that shows you every corner of the room except the view is hiding the view. A description heavy on adjectives and light on specifics is usually compensating for something.
Reviews are useful, but only if you read them sideways. I skim past the ecstatic and the furious, because both tend to say more about the writer's day than about the room. What I want are the calm, specific middle reviews, the ones that mention the thin walls, the steep stairs, the slow morning service, not as complaints but as facts. Those are the people doing me a favor. A recurring detail across several honest reviews is worth more than any rating, and a single thoughtful paragraph from someone who clearly travels the way I do can settle the whole decision.
I also try to book honestly with myself, which is harder than it sounds. It means admitting what I actually need on a given trip rather than what I wish I were the kind of traveler to enjoy. There were years I booked rooms designed for a more adventurous person than I felt like being that week, and paid for it in poor sleep. Now I ask plainly: do I want to be in the thick of it or away from it, awake to the place or restored from it? Answer that first, and the right stay tends to reveal itself.
And when I get it wrong, which I still do, I try to be gracious about it. A disappointing room is rarely a ruined trip. Sometimes it sends you out into a long evening walk you would never have taken from a more comfortable bed, and the walk becomes the memory. Travel has a way of redeeming its own small failures, if you let it.
Underneath all the practical talk, I hold a few quiet convictions about staying somewhere that is not home, and they have less to do with hotels than with how a person moves through the world. The first is that arriving somewhere to sleep is a small act of trust, you are placing your most vulnerable hours in the keeping of a place and its people, and that trust, offered openly, tends to be repaid. The travelers I admire most are the ones who arrive expecting kindness, and so keep finding it.
The second is that the best stays are the ones that change you slightly. Not dramatically, you do not become a different person because of a good room. But you leave a little more able to notice things: the way light moves across a wall, the grace of a well-made breakfast, the quiet generosity of a host who had no obligation to be generous. You carry those noticings home, and they make ordinary life a touch more vivid. That, to me, is the deep purpose of travel, and the stay is where a surprising amount of it happens.
The third is simply that it is worth the trouble. It would be easier to stop caring, to book whatever is cheapest or closest and treat sleep as sleep. But the trouble of choosing well, the reading, the imagining, the occasional happy splurge and the occasional honest mistake, is itself a form of attention, and attention is the whole of travel. To care about where you sleep is to care about where you are. I cannot think of a better thing to care about.
So that is my long thought on stays, set down the way I would tell it to you over a slow dinner, more feeling than formula, more questions than answers. I have tried to be honest about what I do not know and generous with the little I have learned, because that is the only kind of travel writing I trust to read myself. The rest, the actual wandering, is yours to do.
If any of this stirred something in you, I would love for you to keep going. Elsewhere on this blog you will find the stories and guides where I follow these ideas out into real places, the wrong turns that became the best part of the day, the rooms that taught me something, the small lessons of the road I am still learning. Wander through them the way you would wander a new city: with no fixed plan and a willingness to be surprised.
Mostly, though, I hope this leaves you a little more awake to the question the next time you book a place to lay your head. Not just where is cheap or where is grand, but where is true, where will let this particular place reach you. Answer that, and you will sleep well in more ways than one.
Begin small and begin honest. On your next trip, choose just one night to book with real care, a single stay that belongs to its place and matches the kind of day you want to have, and pay attention to what changes. You do not have to overhaul how you travel. You only have to start noticing where you sleep, and let that noticing grow on its own. From there, browse the stories and guides here, and come find me on the road.