Two Coastlines, One Instinct: What Sicily and Portugal Taught Me About Shooting Without a Plan

Modern photography has a technical problem. We obsess over histograms, wait for the “perfect” light, and pack our gear like it’s surgical equipment — all while the actual moment happens somewhere behind the viewfinder, unshot.

I didn’t always think this way. Two decades in management taught me to plan everything, and my early photography followed the same instinct: control every variable, eliminate every risk. Leaving that world behind meant making a different kind of promise to myself — to shoot without a safety net, and trust what’s in front of me over what a manual says I should do.

This spring, three workshops—two through Photo Workshop Adventures in Sicily and Cinque Terre, and one along the Portuguese coast—tested that promise across two very different landscapes.

Sicily: leaning into the noise

Every visitor to Lisbon wants the same clean shot of the yellow Tram 28. But a living city resists postcards. Standing on the cobblestones, I let the overhead wires, the flat grey sky, and the steep pitch of the street shape the frame instead of fighting them.

That instinct followed me to Sicily. Street photography only works if you’re willing to get close — physically and socially. Hiding behind a long lens fifty meters back might feel safer, but it costs you the actual subject. The eccentric artist in wraparound goggles, the vendor serving food in heart-shaped glasses — these are the people who define a place, and you can’t shoot them from a distance.

Autofocus can lock onto a face in a fraction of a second. It can’t manufacture the moment of eye contact that makes the photo worth taking.

Portugal: the trap hiding in plain sight

Photographing a chef at work in Portugal, I noticed something that’s become impossible to ignore on these trips: a phone screen, held up between a person and the thing actually happening in front of them.

It’s everywhere on these workshops now — travelers watching light move across a wall through a six-inch rectangle, checking footage instead of watching it happen. The moment a screen gets between your gut reaction and your surroundings, you’ve stopped making photographs and started making content.

For this stretch of travel, Sony Croatia handed me their latest Alpha body to shoot with — not in a studio, but in exactly this kind of unpredictable, fast-changing light, where a camera either keeps up with instinct or gets in its way.

One test came from an old blue three-wheeled Ape truck rattling past me on an Italian side street. The safe move is 1/1000th of a second — freeze it, keep it sharp. I dragged the shutter to 1/30 and swung the camera with it instead, letting the motion blur do the work a “correct” exposure never could.

Where the coasts diverge

Most travel photography today looks over-processed — flattened, oversaturated, stripped of texture. When students stand in front of a Sicilian cathedral’s heavy shadow, or watch the sky over Portimão and the Algarve catch fire at sunset, my advice is the same: stop shooting the version of the place you’ve already seen in a brochure.

The goal isn’t to document what a place looks like. It’s to get close enough to the mood that a viewer can feel the damp salt air, or the particular silence that settles in right after the light goes.

Sometimes that means pulling color out entirely — letting contrast alone carry the weight of a place’s history, the way it does in the stark geometry of Belém Tower standing against the tide.

The actual lesson

If your camera’s sitting in a bag waiting for ideal conditions, you’re missing most of what this work has to offer. Shoot in weather that makes you uncomfortable. Get close enough to strangers that it feels like a risk. Let a highlight blow out if it means keeping the energy of the moment intact. The settings matter less than you think — the instinct matters more.

I’d genuinely like to hear from you: when you’re shooting somewhere unfamiliar, what pushes you further out of your comfort zone — unpredictable weather and terrain, or the nerve it takes to approach a stranger on a crowded street? Tell me about it in the comments.