San Diego Family Photography | Escondido Family Session

There are certain places that hold more than just memories — they hold the weight of a wedding vow, the landmarks of a brand new chapter, and the subtle beginnings of something bigger than ourselves. For Caity and Ben, that place was Rancho Guejito Vineyard – their wedding venue. It’s where they started their life together, and now, years later, they returned with their baby boy for their very first family session.

It was like coming home.

The First Family Session

This was Caity and Ben’s first photo session as a family of three — a part of their family’s story worth pausing for. Baby N is usually all smiles, but on this particular day he was thoughtful and serious, taking in his surroundings with wide eyes. Caity laughed and said, “You’re never this serious!” and part of me felt that pang of longing that she must have been feeling, the kind that hoped we could capture his sweet, smiley, giggly self – the one she sees everyday – during this family session.

But the thing is…family sessions aren’t about manufacturing the perfect image; they’re about honoring the reality of a season. This season for Caity and Ben looks like holding their boy close, soaking in his every expression, and remembering what it feels like to be right here, right now – sweet baby smiles or not. Someday, they’ll look back at these images and remember the weight of him in their arms, the curve of his little cheeks, and the way their love for one another wrapped around all of them like a warm cozy blanket.

Why Documenting Seasons Matters

Every family story deserves to be told — not just in milestones, but in seasons. The newborn stage. The wobbly first steps. The belly laughs, the shy stares, the tender in-betweens. These moments pass quietly, almost without notice, until one day they’re gone.

Returning to their wedding venue wasn’t just about nostalgia for Caity and her husband. It was about continuity. The same place where they exchanged vows now held their family of three. The same pathways they walked hand-in-hand as newlyweds were now traveled with a diaper bag, and a baby nestled between them.

It’s a reminder that stories grow — they deepen and stretch, and when we pause to document them, we give ourselves a way to hold them close long after the moments have passed.

With Little Ones, Flexibility is Everything

If you’ve ever had family photos taken with a baby, you know they run the show. And honestly? That’s part of the magic. Every session with little ones demands a blend of gentle direction and room to breathe. Sometimes we get big gummy grins. Other times, like with N, we get quiet, thoughtful gazes. Both are beautiful. Both are honest.

Rather than forcing smiles, we focused on connection: snuggles, walks, quiet moments in the same spaces that once held their “I do’s.” It was simple, tender, and real — exactly as it should be.

The Final Images

The images from this session feel timeless. There are classic portraits, yes, but also storytelling images that pull you right into the moment: the three of them walking near the same grove they once stood beside as newlyweds, N chomping on a grapefruit that fell in the orchard, mom and dad pressing a soft kiss on their son’s head while N’s favorite song played in the background.

These are the kinds of photographs that become part of a family’s legacy — the kind that grow more precious with time.

Book Your Own Family Storytelling Session

Your story is unfolding, too. Whether it’s your first family session or your tenth, documenting the season you’re in is one of the greatest gifts you can give yourself and your future generations.

Ready to tell your family’s story? Let’s do it.

xo,

Jess