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The Wrong Question Most Travelers Ask Before a Trip (And a Better One)

May 4, 2026

The Wrong Question Most Travelers Ask Before a Trip (And a Better One)

"What should I do in [city]?" is the default question travelers ask when planning a trip. It gets typed into search engines millions of times a day. It prompts guidebook chapters, travel blog posts, and AI itineraries. It is, in almost every case, the wrong question. Not because it's unhelpful — the results are often technically accurate and sometimes genuinely good. But because it's asking the city to define your experience of it, rather than asking yourself what kind of experience you want.

By Martin Zokov
Planning a Trip When You Have Strong Preferences

Apr 30, 2026

Planning a Trip When You Have Strong Preferences

Most travel planning advice is written for people who are relatively easygoing about what they want from a trip. "Just explore!" "Leave room for spontaneity!" "The best discoveries happen by accident!" That advice is useless if you're someone with specific, non-negotiable preferences. If you hate crowds, actively dislike museums, need live music the way other people need sightseeing, or plan your trips around food to a degree that other travelers find slightly alarming — the standard approach o

By Martin Zokov
Your Trips Are Boring and It’s Your Fault Again

Apr 25, 2026

Your Trips Are Boring and It’s Your Fault Again

Let’s be honest for a second. If your last few trips felt a bit underwhelming, it’s probably not because you picked the wrong destinations. It’s because you planned them the exact same way you always do, which is also how most people plan. You choose a city first, you open a few “things to do” articles, you bookmark some landmarks, maybe add a restaurant or two, and you book a hotel somewhere central so everything is “convenient.” On paper, that sounds perfectly reasonable. In reality, it almost

By Martin Zokov
Why Destination-First Trips Fail Travelers With Strong Interests

Apr 23, 2026

Why Destination-First Trips Fail Travelers With Strong Interests

You've decided to go to Lisbon. You open a browser and type "things to do in Lisbon." You get the same 15 results: LX Factory, Belém Tower, Time Out Market, Sintra day trip. You book the trip. You come home and describe it as "fine." The city was beautiful, but you spent three days doing things curated for a hypothetical average tourist, not for you. This is the failure mode of destination-first trip planning — and it's the default setting of almost every travel tool, guidebook, and AI planner

By Martin Zokov
You’re Planning Trips Wrong and It’s Costing You

Apr 21, 2026

You’re Planning Trips Wrong and It’s Costing You

Most people plan trips the same way. They pick a destination first, lock in dates, and only then start thinking about what they actually want to do. It feels logical. It’s also why so many people end up overpaying and coming back from trips that feel underwhelming. If you’ve ever built a trip like this, you’ve probably experienced the same pattern. You spend more than expected, rush through activities, and still feel like you missed something. Tools like Funizy exist to flip that process, but

By Martin Zokov
The Thing Most Trip Planners Get Wrong: The Live Events

Apr 20, 2026

The Thing Most Trip Planners Get Wrong: The Live Events

If you open any of the major AI trip planning tools today and ask for a five-day itinerary in a city, you'll get a detailed plan. Day-by-day structure, specific restaurant recommendations, museums to visit, neighborhoods to walk. The quality of these plans has improved significantly over the last two years. What you won't get, in almost any of them, is anything specific to the five days you've selected. The itinerary would be essentially identical if you'd chosen a different five days — next mo

By Martin Zokov
The Real Difference Between a Generic and a Custom Trip

Apr 16, 2026

The Real Difference Between a Generic and a Custom Trip

The phrase "personalized travel" gets used in marketing for almost every trip planning tool on the market. It's worth being specific about what it actually means in practice, because most of what's described as personalized isn't. The difference between a generic trip and one that was actually planned for you isn't visible on a map view or in the number of days it covers. It shows up in specific moments during the trip — and, more importantly, in the moments that don't happen. The Generic Tri

By Martin Zokov
Barcelona for Music and Festival Lovers: What to Plan Around

Apr 13, 2026

Barcelona for Music and Festival Lovers: What to Plan Around

Barcelona's music calendar is one of the densest in Europe, but it's organized around a set of anchor events that structure the rest of the year's programming. Knowing what those anchors are — and planning your visit around them rather than treating them as potential bonuses — is the difference between a music trip that works and one that was almost great. The Events Worth Building a Trip Around Primavera Sound (end of May / early June) is the most internationally significant music festival i

By Martin Zokov
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