Dear Travelers, Some of You Are Doing This Wrong

Dear Travelers,

I need to say something that a nicer letter wouldn’t, and I’m saying it precisely because I love that you’re going. You saved for this. You cleared the calendar, found someone to watch the dog, told your boss you’d be unreachable. You are about to spend real money and irreplaceable days on the other side of the world. I want it to be extraordinary. And because I want that, I’m going to tell you the things a brochure never will.

None of what follows is about you specifically, and all of it is about all of us — me included. I have circled a garage in a town that was finished before the automobile was invented. I have packed for a two-week trip like I was fleeing a country. I have stood in the wrong line at the wrong hour for the wrong reason. I earned every one of these opinions the expensive way. Consider this the letter I wish someone had handed me.

So. With love, and with my whole point of view: here are the instincts to unlearn.

Put down the rental car

The rental car feels like freedom, and sometimes it is. Give me a car in the Tuscan hills, the Scottish Highlands, the back roads of the Douro — anywhere the point is the empty space between the towns — and I’ll help you book it myself. There, the car is the trip.

But most people reserve a car for the places where it’s the opposite of freedom. Cities with medieval centers cars were never meant to enter, where you’ll pay for a garage you can’t find, inch through traffic laws written in a language you don’t read, and hand back the keys with two fines you won’t discover until the statement lands. Coastal roads where the whole magic is that someone else drives the cliff while you look out the window. Regions where the train isn’t the compromise — it’s the good part.

A car in the wrong place isn’t independence. It’s a chore you brought on vacation. Spend that money on the driver who knows which pull-off has the view.

Stay long enough for the second morning

The over-mapped itinerary is the most understandable mistake there is. You want to see it, all of it, while you’re there — so the trip becomes a relay. A night here, a night there, bags packed, up at six, on to the next. Eleven pins, twelve nights.

Here’s what that plan doesn’t know: a place doesn’t open up on the first day. Day one you’re a stranger finding the coffee and the water. The place starts giving itself to you on the second morning — when the café already knows your order, when you’ve stopped navigating and started noticing. Leave after one night and you paid the full price of arriving and left before the place paid you back.

The unglamorous luxury of good travel is unpacking once. You’ll always see fewer things this way, and remember far more of them. Nobody’s best trip is the eleventh city they can barely picture.

Decide early — “flexible” is just late

This is the one people defend hardest, because “staying flexible” sounds wise. But there’s a difference between a trip with air in it and a trip you haven’t committed to. When you wait to book, you’re not keeping your options open — you’re waiting for other people to take them. The corner room with the terrace, the table that needs a month’s notice, the guide everyone wants, the flight at a civilized hour instead of 6 a.m.: those go early, to the people who decided early.

Deciding early isn’t rigidity. It’s what buys the calm you were chasing with flexibility in the first place. Early is the relaxed choice. Late is the anxious one wearing a relaxed costume.

Learn ten words. Just ten.

You are not going to become fluent in Portuguese for a week in Lisbon, and no one is asking you to. But hello, please, thank you, excuse me, delicious, the check, good morning, sorry, yes, do you speak English — ten words and a couple of phrases — will change how an entire country treats you. It is the difference between a tourist who arrived and a guest who came prepared. Locals clock the effort instantly, and they reward it with the version of their town they don’t show everyone.

The phone can translate a menu. It cannot do the small human thing that a mangled good morning does at a bakery counter. Do the small human thing.

Walk one street back

The restaurant with photos on the menu, the laminated placard, and a host waving you in from the main square is not where the town eats. It’s where the town feeds people who won’t be back. Walk one street off the piazza — sometimes literally one — and prices drop, quality climbs, and you’re suddenly in the place with no English menu and a grandmother in the kitchen. The best meals of your life are almost never on the square. They’re a three-minute walk and one act of courage away.

Book the marquee thing before you leave home

The Uffizi. The Alhambra. The Last Supper. The Anne Frank House. Sagrada Família. The dinner everyone’s heard of. Every destination has a short list of things that sell out weeks ahead and simply cannot be improvised on the day — and every destination is full of heartbroken travelers who flew across an ocean and got shut out of the one thing they came for, because they figured they’d “sort it out there.”

You don’t sort those out there. You sort them out now. This is exactly the kind of thing an advisor holds in your name while you’re still deciding what shoes to pack.

Don’t cram the day you land

You will step off a long-haul flight dehydrated, time-scrambled, and running on airplane sleep, and you will be tempted to “push through” with a packed first day so you don’t “waste” it. Please don’t. A blown-out arrival day poisons the two that follow. Give landing day a soft landing — a walk, a good meal nearby, an early night. You’re not losing a day. You’re protecting the whole trip from starting in a fog.

Dress like a guest, not a tourist

This isn’t about fashion; it’s about doors. Plenty of the best restaurants, older churches, and finer rooms in the world quietly turn away the athleisure-and-flip-flops look — not to be snobs, but because dressing for the place is a form of respect, and respect opens things. You don’t need a suitcase of finery. One outfit you’d wear to a nice dinner at home is usually enough to be let into rooms that stay closed to shorts and a stadium t-shirt.

Tell me the real number

The one that costs people the most is the least visible: not telling your advisor the truth about the budget. When you shave the number down out of embarrassment, or pad it to seem breezy, I plan the wrong trip — and the gap shows up later as a compromise you feel. I’m not here to judge the figure. I’m here to make the figure go as far as it possibly can, which is the entire reason to work with someone who does this all day. Give me the honest number and the honest priorities. The magic is in the matching.

Why I’d say all this to your face

Not one of these instincts is foolish. Every one comes from something good — wanting freedom, wanting to see it all, wanting to stay open, wanting to not make a fuss. I don’t push on them because you’re doing it wrong in some moral sense. I push because I’ve watched where each one leads, over and over, and I’d be doing a poor job if I let you walk into it just to be agreeable.

That’s the whole model. Not an order-taker who books whatever you hand him, and not an expert who overrules you from on high — but someone in it with you, who has a point of view and spends it on your behalf. You bring the dream. I bring the hundred small corrections that keep the dream from tripping over itself.

Fewer cars. Longer stays. Earlier yeses. Ten words, one street back, and the honest number. It’s slower travel, on purpose — and it is, almost every time, the better trip.

With love, and a point of view, Erik

If you’re planning something that matters, come find me before the map has eleven pins in it — that’s the easiest version of my job, and the best version of your trip. Schedule a call →︎