The Five Questions I Ask Before I Design Any Trip

Every itinerary is a chain of small decisions. Not the big obvious ones — not the destination, not the dates, not which airport — but the hundreds of smaller ones that determine whether the trip feels like it was designed for you or for a general reader who happens to be traveling the same week.

I made the same mistake early in this work that most people make when they plan their own trips: I started with the places. I'd research the destination, build a long list of the restaurants and neighborhoods and must-sees, and try to fit them into days. The result was fine. It had the right addresses in it. But it felt assembled, not designed — a greatest-hits compilation, not a trip with a shape.

The five questions I'm going to walk through in this piece are the part I got to by going backward. I stopped starting with places and started starting with the traveler. Every answer reroutes the trip before a single place gets named — sometimes dramatically. The person who answers question two with "I go to museums for the cafés" and the person who answers it with "I need at least one afternoon in a great collection" are going to get different days even in the same city, even at the same budget, even with the same weather. The questions are how I find the difference.

These are also the questions inside the intake form — compressed and sequenced in a way that fits an initial conversation. If you've already filled it out, this piece is the longer version of what I was asking and why. If you haven't, this is a useful place to start thinking before you do.

Question one: What pace do you want to come home from?

Not what pace do you think you should want, or what pace your last trip was. What pace do you want to come home from — the trip already behind you, already lived.

This question works better in the past tense because the forward-looking version is almost always aspirational. Travelers planning a trip tend to imagine themselves differently than they are: more energetic, more organized, more willing to be at a museum at 9am on day three. The past-tense version forces an honest answer about how they actually feel when they're traveling, not how they want to feel.

The answers sort into three rough shapes. There's the high-pace traveler who wants to be covering ground most of the day — museum to neighborhood to restaurant to late walk, anchored at a place central enough to get everywhere in thirty minutes. There's the slow traveler who wants one thing per day, a long middle, and the afternoon held loose. And there's the most common answer: a trip that starts slow and picks up, or that builds high-energy days around one or two dedicated slow mornings.

What this does to the itinerary is structural, not decorative. A high-pace trip needs geographic sequencing — the museums and the restaurants and the neighborhoods need to be routed so the transitions don't eat hours. A slow trip needs empty space designed in, not the slow mornings bolted on after the fact. A mixed trip needs the pace changes built into the day-by-day shape, so the traveler knows when they're supposed to move and when they're supposed to stay.

The pace answer also determines how I handle the rest of the questions. A slow trip with five must-haves is usually a negotiation — five things don't fit into a slow week without some of them moving. A high-pace trip with a long avoid-list is a sequencing problem — how do I route through everything without hitting the crowded hours. The pace question sets the container. Everything else fits inside it.

Question two: What are the two or three things that have to be in this trip?

Two or three. Not ten. Not everything you've saved to your travel folder. Two or three things whose absence would mean the trip didn't work.

I ask it this way because the discipline of picking two or three is half the design work. Travelers who answer with eight things — and they will, often — are telling me something about their planning anxiety, not about what they actually need. They're trying to hedge against regret by including everything. What they end up with is a trip that visits everything briefly and inhabits nothing deeply.

The must-have list is also how I find the trip's center of gravity. A must-have that reads "I need one genuinely great meal per day, timed right, in a room I care about" is telling me this is a food trip, and the rest of the days need to be built around that rhythm. A must-have that reads "I want one full morning in a neighborhood where I can walk without a plan" is telling me the trip needs unscheduled space as a first-class item, not a leftover. I build around must-haves the way an architect builds around load-bearing walls — they determine the structure, and everything else fits around them.

Two or three also forces a ranking. When two must-haves conflict — and they sometimes do, on a trip where the right food neighborhood and the right slow-walk neighborhood are across the city from each other — knowing which one is first-tier and which one is second-tier resolves the day. If the answer is genuinely "both, equally," that's a signal the trip needs more days, or needs to be a different city, or needs a design conversation before the routing starts.

I hold the must-haves up against everything else in the trip the way I hold any item up against the trip's shape: if it doesn't belong in the days I've designed, it either replaces something that does or it waits for the next trip. The ones that wait are often the hardest to cut in the first revision, and the ones the traveler is least likely to remember missing when they come home.

Question three: What's on the avoid-list?

This question delivers more design information than the must-have list. Every time.

The reason is that must-haves are aspirational — they describe what the traveler wants the trip to include. Avoids are diagnostic — they describe the specific ways previous trips went wrong, or the specific anxieties about this one. The must-have list tells me what to build toward. The avoid-list tells me what keeps breaking.

A traveler who lists "over-scheduled days where I feel like I'm moving between appointments" is telling me something critical about how their trips have felt in the past — probably that they planned their own trips, that the planning anxiety produced a full calendar, and that they came home tired and slightly disappointed. That one avoid entry changes my approach to the whole deliverable. Fewer items per day, visible empty windows, a note in the top sheet that explains the sparse calendar on purpose.

A traveler who lists "tourist restaurants" isn't just flagging a category. They're telling me that the generic recommendation — the place at the top of the lists, the one with the photos everyone has taken — is precisely the thing that made a past trip feel like everyone else's. The avoid is the editorial license to cut harder. I use it.

Some of the most useful avoids I receive have nothing to do with places and everything to do with conditions: "I can't start days before 9am," "I don't want to be in queues," "I need every hotel room to have a window that opens." These are not constraints that limit the trip — they're constraints that improve it. A trip designed around the real traveler's actual conditions is a better trip than one designed around a theoretical traveler who is willing to do anything.

The avoid-list is also how I stop the trip from being everyone else's. The must-haves might be similar across travelers — good food, interesting neighborhoods, time to breathe. The avoids are almost never the same. The specific things that have failed a specific person are, by definition, specific to them. The avoid-list is the most personalizing piece of input in the intake, and the one I refer back to most during the design phase.

Question four: Who are you traveling with, and what do they care about?

The trip design changes completely depending on whether the answer is "myself," "my partner who plans nothing and trusts my judgment," "my partner who has entirely different taste from me," or "three friends who have never traveled together."

Solo trips are in some ways the easiest to design: one must-have list, one pace preference, one set of avoids. The complexity is in the sequencing for one — picking places where a solo traveler is at ease, routing days so the self-directed pace doesn't tip into lonely. The how curated travel works piece covers some of that pattern.

Couple trips where both partners answered the intake form — or where one partner answered and named the other's preferences accurately — have a different structure. I'm looking for the places where the answers overlap and the places where they split. Overlap is easy: that goes in. The split days are the design challenge. I don't average them — that usually produces days that satisfy neither person. I alternate them, or I find places that can serve both purposes in sequence, or I build one big slow morning followed by one high-energy afternoon, naming both explicitly so the traveler knows the structure.

Group trips — more than two travelers — require a shared shape question answered by consensus. Three people who want three different paces don't have a trip yet; they have a negotiation. I don't run the negotiation, but I'll name it directly in the design phase if the intake answers contradict each other. The most useful thing I can do in that case is structure the days so the core shape is there for everyone, and the optional-activity slots are open enough that people can branch for a morning without the day collapsing.

The "who you're traveling with" question also surfaces things the intake form doesn't explicitly ask: who is more familiar with travel, who is more anxious, whose must-haves are harder to satisfy, and who will be the one checking the itinerary at 7am and the one who hasn't looked at it. These patterns come through in how the answers are written, not just in what they say. I try to design for the person who will use the document most and brief the other person in the top sheet.

Question five: What makes you feel like yourself when you travel?

This is the question that trips people up the most, and the one that does the most design work once it's answered.

The other four questions are largely about preferences — pace, must-haves, avoids, group dynamics. This question is about identity. Specifically: when you are traveling at your best, when the trip is working, when you arrive at dinner and you know this is exactly where you should be — what is the condition that made that possible? What does it look like when the trip is giving you the version of yourself you came for?

Travelers who've thought about this before usually answer quickly and specifically. "I feel like myself when I have a slow morning and nowhere to be before 10." "I feel like myself when I'm eating at a bar and talking to whoever's next to me." "I feel like myself when I'm walking through a neighborhood for the first time and I'm slightly lost and I don't mind." These answers are design instructions. I build toward them.

Travelers who haven't thought about it often give me the more interesting answers. They start with an activity ("when I'm hiking" or "when I'm at a good restaurant") and work backward, because I'll ask them to. Why does hiking do that for you — is it the physical movement, the solitude, the landscape, or the sense of being away from the accessible? The activity is usually a proxy for something more specific, and the more specific thing is what I can actually design around.

The answer to question five is also the answer to the hardest revision conversation I have with travelers: the one where I've cut something they wanted, and they're asking why. When the cut item contradicts the condition named in question five — when it's a high-energy activity on a trip whose shape is "I feel like myself when I have space to think" — the revision conversation is short. The cut holds. The trip's shape serves the traveler's answer.

This question is also the closest thing I have to a quality test for the finished deliverable. Before I send the document, I read through it once with question five as the lens. Does this trip create the conditions under which this person feels like themselves? Not does it hit the must-haves (that's a checklist), not does it avoid the avoids (that's an edit), but does the overall shape of the week deliver the thing they named. If yes, the trip is done. If not, something in the sequencing or the pacing needs another pass.

How these five feed the design phase

These five questions are not a form. They're a brief. The design phase — the actual work of building the itinerary — starts from the brief and works outward.

The intake form is where I collect these answers, along with a few supporting questions that help me with logistics and sequencing. Once I have the answers, the design phase works roughly in this order: I lock the pace, I place the must-haves, I apply the avoid-list as a cut filter, I structure the days around who's traveling and how they'll actually use the document, and I read everything back through the lens of question five before I finalize.

The output of all of that is an itinerary that looks sparse on paper and full in practice. The days have centers of gravity, not schedules. The open windows are designed, not empty. The cuts are visible, because the visible cut is the editorial signal — it shows the trip was designed and not just assembled.

The depth of the design phase varies by project. The service tiers describe what each level of curation includes — the shorter format that fits a five-day single-destination trip is a different scope from the deep version built for a multi-week itinerary, but the five questions are the same brief regardless.

The five questions are the part that doesn't show up in the deliverable. What shows up is the trip. But the five questions are why the trip works.

What to read next

If you're thinking about how this connects to the broader approach, how curated travel works is the longer version of the editorial philosophy underneath all of this — how I decide what goes in, and why the cut is often the more important skill.

If you're ready to start: the intake form is where the conversation begins. It's designed to take less than ten minutes and to be completable on a phone. The five questions above are inside it, shaped for an initial brief. Everything that comes after is the design.