An engagement shoot is more than a box to check before the wedding day. At its best, it’s a chance to slow down, step into your story as a couple, and create imagery that feels deeply personal. When that shoot happens in a destination like Florence, Italy, it becomes something even more powerful: part love story, part travel memory, part artistic collaboration.

And speaking of artistic collaboration, last fall, a photography workshop organized by the founders of The Wedding Masterclass (a conference for the wedding industry) collaborated with expert destination wedding photographer and repeat contributor to Destination I Do, Collin Pierson, to lead an engagement shoot in Italy. This Florence engagement session is a perfect example of how location, fashion, and connection come together to elevate the entire experience. 

Known for his editorial yet emotionally grounded approach, Collin has built a reputation for creating images that feel both cinematic and intimate. His work blends natural movement with thoughtful composition, allowing couples to feel like themselves while still stepping into something elevated and timeless.

Nathan Jaffan and Caitlin Grace captured images alongside Collin, learning some of his trusted techniques while putting their own talents to use. You’ll see all three of their images in this article – each noted with credit. The couple, Elena & Lorenzo made for perfect subjects in one of the world’s most beautiful cities.

Why a Destination Engagement Shoot Changes Everything

Choosing a destination for your engagement shoot immediately shifts the energy. Florence isn’t just a backdrop; it’s a living, breathing character in the story. From the golden light bouncing off centuries-old stone to the winding streets and bustling piazzas, the city offers layers of texture, history, and romance that simply can’t be replicated at home. “When you’re photographing in a city like Florence, the key is intention over perfection,” says Collin Pierson. “Busy places like Piazzale Michelangelo can feel overwhelming, but with the right planning, patience, and timing, they add energy and authenticity. I always encourage couples to focus on each other, not the crowd. When the connection is real, the city becomes part of the story rather than a distraction.”

If you’re wanting to include a variation of backdrops to your experience, Pierson has some advice. “Little things like stopping in to a small bar (which in Italian means a “coffee” bar,)  to shoot photos or a quick jaunt to a train station (which is very fashion forward,) are ways to add layers to your shoot.”

Being in a destination also helps couples relax into the moment. You’re already out of your routine, more present, more open, and often more affectionate. That ease translates directly into the images. Instead of stiff poses, you get genuine laughter, soft glances, and movement that feels natural. The result is a collection of images that don’t just show what you look like together, but what it feels like to be together in that place and season of life.

Fashion Isn’t an Afterthought — It’s Part of the Story

What you wear plays a huge role in how your engagement photos feel, especially in a destination setting. Fashion sets the tone. In Florence, that might mean flowing silhouettes that catch the breeze, tailored pieces that echo the city’s elegance, or a palette that complements the warm, earthy tones of the architecture.

The key is choosing clothing that works with the destination, not against it. Highly structured outfits can feel out of place on cobblestone streets, while loud patterns may compete with already visually rich surroundings. Neutral tones, soft textures, and intentional layering tend to photograph beautifully in historic European cities. Comfort matters too. If you’re constantly adjusting your outfit or worrying about your shoes, it will show.

When fashion aligns with location, the images feel cohesive and timeless rather than trendy or forced. 

Building a Relationship Before the Wedding Day

One of the most overlooked benefits of an engagement shoot is the opportunity to build a genuine connection with your photographer. By the time the wedding day arrives, your photographer shouldn’t feel like a stranger showing up with a camera. They should feel like someone you rely on completely. “An engagement session is where trust really begins,” says Pierson. “It’s not just about getting comfortable in front of the camera, it’s about learning how your photographer sees, how they move through a space, and how they tell a story. The same happens for your photographer, learning how a couple interacts and how to pull out the best in them. By the time the wedding day arrives, that connection allows couples to be fully present, because they already know they’re being seen and understood.” 

That mutual understanding leads to better communication, more ease, and stronger images on the wedding day when emotions are high and timelines are tight.

The comfort you build beforehand allows them to document your wedding not just as an observer, but as someone who already understands your rhythm and your story.

In the end, an engagement shoot, especially in a place like Florence, isn’t just about photos. It’s about creating space for connection, intention, and artistry before one of the most meaningful days of your life.