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What Painting in Italy Taught Me About Design

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Spoiler: I’m No Michelangelo

This past August, I spent two weeks traveling through Italy (per the ST8MNT tradition of sending employees on a sabbatical once you hit your 5 year anniversary). During the two weeks we travelled from Venice to Florence, down the coast to Cinque Terre, and ended in Rome. While the trip was a chance to step away from the day-to-day, it also became something else entirely: an opportunity to slow down and reconnect with creativity in a more analog, observational way.

I brought along a small watercolor kit I built myself with Winsor & Newton paints arranged into a travel tin, a few pens for line work, some compact brushes, and a sketchbook. My water cup was whatever I had on hand at the moment—water, beer, even an Aperol spritz once or twice. It was simple, portable, and served me well.

What I didn’t expect was how much that small act—sitting down and painting—would reshape how I think about design.

My Travel Art Kit, image that lays out all of the materials in the travel art kit including pens, pencils, clips, watercolor pants, etc.
Everything I packed along with me to make art

Slowing Down to See More

Most of my painting happened while we were on the go: sitting in piazzas with an aperitivo, tucked along canals in Venice (spritz in hand), at the rocky beaches in Monterosso, in the Boboli Gardens, or on the balconies of our Airbnbs. Each environment a delightful mix of architecture, humans, sounds, textures, etc.

Painting forced me to slow down in a way that photography never quite does. You can’t rush a watercolor. You have to look longer. You have to decide what matters.

As designers, we often move quickly—scanning, selecting, refining. But this process reminded me that observation is a skill, and it gets stronger the more time you give it. The longer I sat with a scene, the more I noticed: subtle color shifts, the way shadows softened edges, how textures layered on top of one another.

That kind of seeing translates directly into design.
Collage of images showing a scene in Venice, the tablescape of painting while having aperitivo along with the watercolor painting of the canal
Painting along a canal in Venezia

Italy as a Living Collage

One of the most striking things about Europe in general is how layered everything feels. The design of each building is like a living archive. Generations have added to them: signage, repairs, paint, graffiti, ornamentation. Nothing feels overly precious, but everything feels meaningful.

It’s a collage of time.

In Florence, I noticed a stone shop sign for Corsani carved with a custom typeface that had a modern flair, yet felt like it could have been there forever. Nearby, a hand-painted Tipografia sign carried a completely different energy—more immediate, more expressive. Both coexisted naturally.

There were hand-painted gold window signs on restaurants, vintage exterior signage like Mario, layered street art, and record shops that kept their original signage from decades ago alongside newer updates. At Santa Croce, even the floor tiles told stories—ornate typography and skull mosaics woven into the space.

A collage of images from travels to Firenze, including the statue of David, some nice signage typography and the Birth of Venus

In Rome, Roscioli’s branding stood out immediately—a refined logotype that translated seamlessly into neon signage and extended into beautifully designed collateral throughout their salumeria. At the Vatican Museums, I was struck by handwritten notes from Matisse—surrounded by delicate, spontaneous drawings of filigree and flowers.

A collection of images featuring the Roscioli brand in Roma, including neon signage, swag and tablescapes

In Venice, I found small street shrines covered in layers of paint, offerings, and time. Restaurants like Ristorante da Ivo used stained glass lanterns as signage—function, storytelling, and identity all wrapped into one object.

A collection of images from Venezia featuring stained glass lantern signage for restaurants

None of these elements felt isolated. They built on each other.

That idea, that design doesn’t exist in a vacuum, but instead lives within layers of context—is something I want to carry into every project.

Images of the tablescape featuring watercolors and aperol spritzes along with the view from the balcony and a painting of the view
View from our Airbnb in Roma

Let the Medium Free You

Watercolor is unforgiving in a way that digital design isn’t. You can’t Command+Z your way out of a bad stroke. You have to adapt. Work with it.

Images painting from a rooftop terrace of a view of the duomo featuring a watercolor painting
View from the rooftop terrace of our Airbnb in Firenze

With this, I found myself making quicker decisions, trusting instinct more, and embracing imperfections as part of the final piece. Color relationships became more intuitive, less about exact values and more about feeling. Composition became about balance and movement, not perfection.

Painting palette and view of landscape at Boboli Gardens, along with the finished watercolor painting
Painting at Giardino di Boboli in Firenze

As an art director, it reminded me that not everything needs to be over-refined to be effective. Sometimes the energy of the idea matters more than the precision of the execution.

Scenes of watercolor painting set up in Vernazza in Cinque Terre along with a watercolor painting of the colorful buildings
Painting along the streets in Vernazza in the Cinque Terre Region

 

Italian door way along with a pen line drawing of the doorway in Rome
The last day of our trip, featuring a drawing of a doorway in Roma

Composition with the Grand Canal in Venice in the background, along with images of package design layered on top

Design is in the Details

Beyond the landscapes, design compositions were catching my eye left and right.

It’s no secret that Italian package design is known for it’s extravagance. All of the packaging on the shelves felt considered down to the smallest detail. Candy tins that were so well designed they felt like keepsakes (and they became keepsakes in my case). Restaurant identities that extended into menus, signage, interiors, and merchandise without feeling overbranded.

That sense of cohesion—of branding that feels embedded rather than applied—is definitely something we strive for at ST8MNT. Seeing it executed so naturally reinforced how powerful that approach can be.

Stepping away from screens and working with your hands changes how you think. It reconnects you to fundamentals: observation, composition, storytelling.

Traveling through Italy reminded me that great design isn’t just about aesthetics, it’s about context, history, and human experience. It’s about how things live, breathe, and grow over time.

Creative travel fuels better design.
Observation is a designer’s superpower.
And sometimes, the best way to grow digitally is to step back into something analog.