I Planned 15 European Cities in One Year. Here’s What I’d Never Do Again.

I planned and visited fifteen European cities in one year. It looked incredible on paper — efficient routes, full calendars, seamless logistics. The kind of travel people dream about. And in many ways, it was. But once the novelty wore off, I realized something important: some of the ways I planned those trips were quietly working against the experience I thought I was creating.

One of the biggest mistakes I made was moving too often. One- and two-night stays seemed logical at the time, like I was maximizing the trip. In reality, every move carried a mental cost I hadn’t fully accounted for. Checking out, storing luggage, navigating a new transit system, orienting myself in an unfamiliar neighborhood, figuring out food all over again — even when everything worked, it added up. Some of my most draining days weren’t packed with sightseeing — they were transition days, where I technically arrived somewhere new but never really landed. I learned quickly that a city doesn’t start to feel like a place until you’ve been there long enough to stop performing your trip. By the third or fourth day, something shifts. You recognize streets. You return to the same café. You stop checking your phone every few minutes. That’s when a place begins to open up.

I also fell into the trap of treating cities like checklists. The thought crept in more than once: I may never be back, so I should see everything. Ironically, those are the trips I remember the least. Landmarks blur together when they’re rushed. Museums lose their impact when they’re stacked back-to-back. Even incredible meals become forgettable when they’re eaten between obligations. Some of my favorite memories from that year weren’t iconic at all — they were slow walks through the same neighborhood, grocery shopping like a local, lingering over one great meal instead of squeezing in three. It made the trip feel more alive.

Another lesson I learned was the difference between planning around time and planning around energy. Many of my itineraries were perfectly logical. The trains ran on time. The opening hours worked. The distances made sense. But logic doesn’t account for jet lag, heat, crowds, or decision fatigue. Those things compound quickly, especially when you’re moving often. There were days where everything was technically doable, but nothing felt enjoyable — not because the plan was bad, but because it didn’t respect how travel actually feels in your body. Now, I think far more about slower mornings, fewer fixed commitments, and rest before it’s urgently needed. A good itinerary doesn’t just manage your schedule; it protects your energy.

Where I stayed also mattered far more than I expected. I used to choose a city first and figure out the neighborhood later. Now I do the opposite. The place you sleep, eat, and walk through every day shapes your entire experience. Two people can visit the same city and have completely different trips based solely on where they’re based. Some stays felt effortless. Others felt like work, even though the city itself was incredible. When your neighborhood works, so many small frictions disappear without you even realizing they were there.

And then there was over-optimizing. I like systems. I like efficiency. I like making things work well. But travel doesn’t reward perfection the way spreadsheets do. Some of my least favorite moments came from trying to make a trip optimal — squeezing in one more city, catching the earlier train, adjusting plans to save a little time or money. Some of my best moments came from doing the opposite. Staying an extra day. Skipping something “important.” Choosing ease over efficiency. Optimization is useful until it crowds out joy.

That shift — from optimizing trips to designing experiences that actually feel livable — is what ultimately changed how I plan travel today. When I plan trips now, for myself or for clients, I prioritize fewer bases, longer stays, realistic pacing, and neighborhoods that support real life, not just sightseeing. I leave room for rest and spontaneity, because that’s where the most memorable moments tend to happen. Most of all, I plan trips that feel good while you’re in them, not just impressive when you describe them afterward.

If you’re planning a trip and feeling pressure to see everything, move constantly, or make it feel “worth it,” you’re not alone. Most travelers are given the same advice. But travel doesn’t have to be exhausting to be meaningful. If a slower, more thoughtful approach resonates, that’s exactly how I plan trips — and I’d love to help you design one that actually feels good while you’re living it.