What 66 Trips Taught Us About Traveling as a Couple

G and I have taken 66 trips together since 2019. Hotels on four continents. Flights we've lost count of. One engagement in a vineyard courtyard in Paso Robles. A cat who traveled with us from Toronto to Fort Lauderdale screaming the entire flight. Seven years of airports, hotel rooms, restaurant reservations, missed turns, lost luggage, and conversations on rooftops after the fireworks end.

Here's what we've figured out. None of it is advice. All of it is true.

G packs for the trip she wants to have. I pack for the trip that's actually happening. She brings options. I bring systems. She has a process that involves laying everything out on the bed, editing it down, adding three things back, removing one, and then packing two suitcases regardless of how long the trip is. I have a process that involves putting things in a bag. Both approaches work. Neither person understands the other's.

In seven years of traveling together, G has never taken fewer than two suitcases on any trip longer than three nights. I have never understood why. I asked once, early on, and she said "because I might want choices" and the way she said "choices" made it clear that this was not a discussion. It was a statement of fact. The suitcases come. I carry them. We are both fine with this arrangement. I am more fine with it than I used to be, which I think is called growth.

G taught me this. Not by saying it. By giving me a look every time I reached for my phone at the pool or the beach. The look is subtle. One raised eyebrow, a slight tilt of the head, and a silence that communicates more disappointment than a 30-minute lecture could. I've put my phone away every single time. She's right. The phone doesn't belong at the beach. I know this. I know it the way I know I should drink more water and stretch before running. I know it and I keep reaching for the phone and she keeps giving me the look and I keep putting it away and one day I'll learn to just leave it in the room.

The Palm Beach trip in 2025 was the worst. I brought my phone to the beach. She gave me the look. I put it away. I picked it up 20 minutes later because I thought of something for work. She gave me the look again. I put it away. I picked it up 10 minutes after that because I wanted to check something. She didn't give me the look. She just turned a page in her book very slowly, which was worse. I left the phone in the room for the rest of the trip. Progress.

G window-shops the way some people run or meditate. Worth Avenue in Palm Beach. The boutiques on the Ringstrasse in Vienna. The shops on Bloor Street in Toronto. The vias in Palm Beach (twice). The fashion street in Venice whose name I don't remember because I was following her and not paying attention to street signs.

The process is always the same: she walks slowly, she stops, she looks at something in a window, she points at it or tilts her head at it, I nod or say "that's nice" (both are acceptable), and we move on. Nobody buys anything. Nobody's credit card gets hurt. The whole exercise takes about 45 minutes and at the end of it she's calmer and happier than she was before, and I've spent 45 minutes walking with the person I love through a beautiful city, which is not a bad deal even if I don't understand the mechanism.

We've done this in enough cities now that it's become ours. I've stopped questioning it. I've started looking forward to it.

G finds the restaurants. Every trip. She researches weeks ahead. She reads reviews in languages she doesn't speak using Google Translate. She texts friends who've been to the city. She scrolls through food accounts on Instagram. She builds a running list in her phone that's organized by neighborhood and meal type. By the time we land, she has a spreadsheet's worth of options and I have nothing, which is the correct distribution of labor.

This system has produced Bestia in LA, Osteria alle Testiere in Venice, Lotus of Siam in Vegas, a signless taco shop in McAllen, a rooftop riad in Fes, and a strip-mall Thai place in Orlando that changed how I think about pad see ew. I have contributed exactly zero restaurant discoveries in seven years. I contribute the wine selection when she lets me, and the willingness to eat at whatever time she decides is optimal, which is usually either very early or very late because she's read that the best seating is at 5:30 or 9:45.

Find your food person. Trust their spreadsheet. Marry them if possible.

G has a pool protocol. She arrives early. She selects a chair based on sun angle, proximity to the bar, and shade availability for later in the afternoon. She arranges the towels. She positions the sunscreen, the book, the hat, the sunglasses, and the drink in an arc around the chair that I think of as her command center. She then rotates the chair every 45 minutes to track the sun, which she does at every pool at every resort in every country we've visited. At the DoubleTree near the Orlando airport, which is a standard hotel pool next to a parking garage, she did the full setup and suddenly the pool looked like a vacation. She has this ability to turn any pool into a resort experience through sheer force of arrangement.

My pool strategy: find chair, sit in chair, possibly swim, look at phone, get the look from G, put phone away, possibly swim again. Our strategies are incompatible and that's fine.

On the hotel rooftop in Palm Beach after the fireworks ended and nobody wanted to go inside. In the car driving through Paso Robles the morning after the engagement with the windows down and no music. On the Brightline when G is supposed to be napping but starts talking instead. Walking through the ByWard Market in Ottawa at midnight after New Year's Eve, the streets empty and covered in fresh snow. On the top deck of a cruise ship in the Caribbean watching phosphorescence in the wake and not saying anything for a while and then saying everything.

You can't schedule these conversations. You can't force them over dinner or during a "let's talk about our plans" session. They happen in the in-between moments: the walk back to the hotel, the quiet after the activity, the last hour of a long train ride. The trips that produce the best conversations are usually the trips with the most unstructured time. The agenda is the enemy of the real conversation.

G doesn't say "this is nice." She doesn't rate things on a scale. She says "when are we coming back?" which is the highest compliment she gives a place and also an immediate shift from present tense to future planning. She said it about the Allegretto in Paso Robles. The Heuriger wine taverns in the hills above Vienna. The pool at the Hotel Valley Ho in Scottsdale. The bridge between McAllen and Reynosa. The Rabot Hotel terrace in St. Lucia.

It used to confuse me. We'd just arrived somewhere and she was already talking about coming back. Now I understand: the planning is the feeling. When G starts talking about the return trip, it means her brain has shifted from experiencing the place to imagining a future with the place in it. If she's quiet and just looking around, the place is fine. If she's on her phone looking up flight prices before we've checked in, the place is great.

G buys spices in every city we visit. Ras el hanout from a vendor in the Fes medina who ground it fresh while we watched. A spice blend from the Chelsea Market in New York. Honey from a market in Dubai. Something I can't identify from a stall in Seoul. Za'atar from a shop in Vienna (Vienna has za'atar, apparently). Our kitchen has a shelf that is essentially an atlas of everywhere we've been, organized by nothing, labeled in multiple languages, and used constantly.

I stopped asking "do we need that?" about four years in. We always need it. Or she always finds a way to use it. The ras el hanout from Morocco goes into everything now. The honey from Dubai went into a salad dressing that was excellent. Every trip produces a jar or a bag or a bottle, and every jar or bag or bottle ends up in a dish I eat six months later and think "oh, that's the Fes one."

G says she doesn't like dogs. She has said this multiple times, in multiple cities, with conviction. She is wrong.

On the rooftop of the Palm House Hotel in Palm Beach on July 4th, a couple brought their dog, who was wearing an American flag bandana and looking profoundly unimpressed by the fireworks. G was charmed. I reminded her she doesn't like dogs. She said "I don't like dogs in general. I like specific dogs." This is a distinction she has made before. In Trinity Bellwoods Park in Toronto in 2022, she spent 20 minutes petting a stranger's golden retriever while insisting she is not a dog person. In Vienna, she stopped at a cafe because there was a dog sitting outside looking at her.

The criteria for "specific dogs" remains unclear. I've asked. She can't articulate it. It appears to be an instinct-level judgment that operates independently of any stated preference. Seven years. I've given up trying to understand it.

Travel doesn't fix a relationship. It stress-tests one. You're tired, you're lost, the hotel is worse than the photos, the restaurant is closed, the flight is delayed, and someone has to decide what to do next. All the small negotiations that happen invisibly at home become visible and loud on the road. Who holds the passports. Who checks in. Who tips. Who asks for directions (G, always, because I'd rather walk in circles for 40 minutes than admit I don't know where I am, which is a flaw she has learned to work around by asking for directions while I'm in the bathroom).

We've had bad hotels, bad meals, bad weather, and one very bad Spirit Airlines experience that I'm still not over. We've never had a bad trip. Because the trip was never about the hotel or the meal or the weather. It was about the person next to me on the plane, in the Uber, at the restaurant, on the rooftop after the fireworks. G is the trip. Everything else is scenery. I proposed to her in a vineyard courtyard in January because I'd known that for seven years and it was time to say it out loud.