If you know me (or have spent time exploring my little corner of the Internet), you already know that I believe the sweetest photos often happen in between the “big” moments. Not when we’re perfectly posed, but in the moments we don’t even realize we’re seen. That’s where the real magic lives. This dazzling session in Pienza, Italy puts that magic on display.

Last summer, I had the wild luck of spending two weeks in Italy—camera in hand, heart wide open. I’d posted about my travel dates on Instagram, the way I do before a new adventure, and that’s how Amy and Gerald found me. They’d just gotten engaged and wanted to celebrate with photos in Tuscany. We landed on a quiet evening in Pienza. Just the three of us, wandering ancient streets together. This tiny town hums with rich culture and storied traditions. It’s just the kind of place most of us envision when we think of Tuscan charm. Pienza is a little-known gem, away from tourists and crowds, and it’s a great location for taking in the scenery your own way on your own time, making it ideal for an intimate couple’s session.

Why Overcast Skies Are a Photographer’s Secret Gift

I’ll be honest—when we met up, the sky was more silver than blue. The clouds were thick, letting just a few surprise rays peek through every now and then. If you’ve ever planned a photoshoot (or just wanted a sunny vacation day), you know that little sigh you let out when you see clouds rolling in. Amy and Gerald mentioned it, too. “We were hoping for that golden Tuscan glow,” they said, half-laughing.

Here’s the secret, though: some of my favorite sessions happen under overcast skies. It’s like the universe pulls out a giant, soft blanket of light and drapes it over everything. No harsh shadows, no squinting, no heat making everyone sticky and tired. The colors glow differently—the bricks become deeper and richer, the green shutters pop, and the fields turn an earthy, vibrant green. Flowers show off a little more. Even the rolling hills seem to stand taller, every curve and line visible.

So, if you ever find yourself worried about the weather, don’t be. Sometimes, clouds bring out the details that direct sunlight overpowers. Amy and Gerald’s session is a beautiful example.

What to Look for When Taking Pictures at a New Location

If you’re ever in a new place and itching to make some memories, here’s a little trick I use when looking for places to take photos: I look for three things—landscapes, architecture, and vantage points.

• Landscapes: Wide open spaces. Fields, hills, forest, or even a city square at just the right angle. Look for places with room to breathe and visual interest. Check, check, and check in Pienza—it offered some of the most idyllic landscapes I’ve ever had the joy of photographing.
• Architecture: Old doors, textured walls, stoops, or staircases. Buildings carry stories, and they frame the people in them in the most unexpected ways. Of course, Tuscan towns have plenty of storied architecture to work with!
• Multiple Vantage Points: Don’t settle for one spot. Circle around, look up, crouch down. Sometimes the best photo is from the ground, looking up at someone’s laughter as they tip their head back. We utilized meadow, street, and hilltop to add more variety to Amy and Gerald’s session

But it’s not about the “best” spot. It’s about the one that feels right. An unexpected alcove as we transition scenes. The terrace where Gerald stole a kiss. Or the narrow alley where we paused, waiting for the light to change.

You don’t have to have a plan mapped out, either. Sometimes, the best photos happen when you leave space for the unexpected. Like the way the light broke through the clouds just when Amy and Gerald walked through an archway at the end of the session—a sweet, cheerful finale. 

Letting Yourself Be Seen

That’s what I try to hold space for, every time I work with couples or families or friends. Not just the “smile here, stand there” stuff, but the fits of giggles and the shy glances and the hand squeezes that say everything without a word.

Amy and Gerald let themselves be seen—any nerves, all the joy, a bit of silliness, and all the sweet pieces that make up their story. That’s what I hope to do for everyone who steps in front of my lens.

If you’re reading this and feeling a little nervous about your own session (whether it’s in Tuscany or your own backyard), I’m here to remind you: You don’t need a perfect day. You just need to show up as you are. The good stuff is already there, waiting to be noticed. 🌿

Make Your Engagement Session an Adventure

Be sure to follow me on Instagram (@iasiskennedyphotography) to view my travel schedule — I may be coming to you!