How I Plan Every Trip

People often ask me how I plan trips — how I find the right hotels, which restaurants to prioritize, how I build an itinerary that feels effortless but actually leaves room to breathe. The honest answer is that it took years to develop a process, and I’m still refining it.

But there are a handful of principles I come back to every time, regardless of where I’m going. Here’s how I approach planning a trip from start to finish.

Start With How You Want to Feel

Before I open a single browser tab or look at hotels, I ask myself one question: how do I want to feel on this trip?

That might sound abstract, but it’s the most important decision you’ll make. Do you want to feel restored and slow? Adventurous and active? Romantic and indulgent? Social and spontaneous? Once you know the answer, everything else — where you stay, how you spend your days, where you eat — flows from that.

A trip that leaves you more exhausted than when you left isn’t a vacation. It’s a missed opportunity.

Choose Your Base Wisely

I always start with accommodations, because where you stay shapes everything else. I’m partial to boutique hotels and smaller properties — the kind of place that feels like it belongs to the destination rather than a global chain.

Some things I look for: Is it walkable to things I actually want to do? Does it feel like the kind of place that will take care of me? Does the aesthetic match the energy of the destination?

Proximity matters more than people think. Staying in the right neighborhood eliminates a surprising amount of friction.

Research Like a Local

The best travel recommendations don’t come from the top ten lists. They come from people who actually live in a place.

For every destination, I look for local food blogs, neighborhood Instagram accounts, and recommendations from people who live there. I look at what locals are posting rather than what’s been optimized for tourists.

I also pay attention to what good friends with similar taste have recommended. That word-of-mouth network is often the most reliable source I have.

Build a Loose Framework, Not a Schedule

I don’t schedule every hour. Instead, I think in terms of anchors: one or two non-negotiables per day that are worth planning around, and then space for everything else to happen naturally.

The best travel moments are almost always unplanned. The coffee shop you wandered into. The neighborhood you decided to walk through. The conversation that led you somewhere you hadn’t considered. You can’t plan for those, but you can leave room for them.

Pack Intentionally

Overpacking is one of the most underrated sources of travel stress. I pack for the trip I’m actually taking, not the hypothetical version where I need six outfit changes.

I carry on whenever possible. It keeps me nimble and saves at least 30 minutes on every trip.

A Note From Kristina

What I’ve learned is that the best trips aren’t always the most meticulously planned ones. They’re the ones where you knew what mattered most and stayed flexible about everything else. Planning well means creating the conditions for good things to happen — and then getting out of your own way.