Winter Park Engagement Session at Rollins College & Hannibal Square
European charm, a break in the rain, and the sweetest pup
There’s something about Winter Park that just brings the charm to an engagement session: brick pathways, ivy-draped archways, and the soft buzz of streetside cafes that brings all the romantic European feels. For this particular engagement session, we leaned fully into that charm, exploring both the classic architectural elegance of Rollins College and the more Ivy covered nature of Hannibal Square.
As an Orlando wedding photographer, I’m always looking for Florida engagement session locations that feel timeless yet full of life and this session was exactly that.
The Magic of Overcast Light
We lucked out with a break in a rainy weekend for this shoot. I think it was the only 1-2 hours where it wasn’t raining the whole weekend! But cloudy skies can be such a good thing! Overcast skies are like nature’s softbox, wrapping everything in a soft, even glow that flatters every angle and opens up so many creative options, that we wouldn’t have on a sunny day.
The locations and angles to use at Rollins College, especially, depends on the lighting of the day. On a sunny day, we would often work around pockets of harsh shadows and avoiding hot spots through the trees.
On this day though, we had complete freedom to shoot from every angle of the chapel, including corners that would be far too backlit or bright on a sunny day. The soft gray skies gave us rich skin tones, less squinting, and a dreamy, romantic mood that can’t quite be replicated with sunlight. It’s one of the reasons this session feels so distinct—every engagement session here can look entirely different depending on the light.
European Vibes at Rollins College
There’s no denying the romantic appeal of Rollins College. Between the Mediterranean-inspired architecture, stone arches, and carefully manicured grounds, the campus gives off major Italian-coast-meets-Florida energy.
We strolled the long breezeways, paused under the grand arch of the chapel, and made the most of quiet corners where the ivy climbs just right. The historic white walls, terra cotta roofs, and vintage lanterns created the perfect backdrop for genuine connection without overpowering the couple’s emotion.
Hannibal Square: A Hidden Gem
After soaking in all the elegance at Rollins, we made our way to nearby Hannibal Square—a spot I often recommend for couples who want something classic but with a bit more of an urban edge.
Hannibal Square is filled with texture—old brick walls, charming storefronts, tree-lined sidewalks—and that little mix of history and quirk brings a totally different feel to your engagement session gallery. It’s also typically quieter than Park Avenue, which gave us space to play, laugh, and let the couple just be themselves without feeling like we were on display.
Meet Lisha, Josh, and Their Pup, Janie
Lisha and Josh are one of those couples who are effortlessly connected. The kind of people who make each other laugh without even trying. From the moment we met up for their Winter Park engagement session, they were warm, relaxed, and totally present with each other—and with their sweet pup, Janie, by their side.
Bringing Janie along wasn’t just a fun idea for them—it was important. She’s a huge part of their lives and already makes up a piece of the little family they’ve started building together. Including her in the engagement session was their way of honoring that bond and weaving their full love story into these photos.
And she was such a good girl the entire time.
Bring the Dog (But Bring Help Too!)
If you’re considering bringing your pup to your engagement session, I fully support it—just like I did for Lisha and Josh. But here’s my biggest tip: bring someone to help handle the dog. Whether it’s a friend, a sibling, or even a trusted dog-sitter, having an extra set of hands makes the entire experience smoother and more enjoyable.
For this session, having someone to help wrangle Janie meant we got the best of both worlds: heart-melting photos of the three of them together, and plenty of uninterrupted moments of just the couple. Their helper stood just behind me, calling Janie’s name or squeaking a toy to get her attention—leaving Lisha and Josh free to focus on each other.
Genuine Posing and Real Connection
My approach to posing is always rooted in authenticity. I’ll guide you—so you’re never wondering what to do with your hands—but I always want you to look and feel like you. That means encouraging movement, prompting laughter, and creating space for real connection.
Throughout this session, we laughed a lot. We wandered, we twirled, and there were so many little in-between moments that showed just how much Lisha and Josh adore each other. The kind of warmth that doesn’t need big gestures to be felt—it just shows up in the way they look at each other, how they hold hands, or how they instinctively lean into the quiet moments.
That’s what I love most about being an Orlando wedding photographer—getting to witness that kind of real, unscripted connection and preserve it through photographs.
Looking Ahead to Their Wedding
I’m already counting down the days to their wedding next year. These two are so excited to make it all official, and if their engagement session was any indication, their wedding day is going to be filled with just as much laughter, emotion, and heart.
Their love for each other—and for the little life they’ve already built with Janie—is so genuine and beautiful. And capturing this moment in time, right before everything changes again, was such a joy.
Thinking of Your Own Session?
Whether you’re dreaming of a romantic, cloudy-day session at Rollins or something sun-drenched along the coast, I’d love to help you create images that feel like you. As a Florida engagement photographer, I’ve spent years exploring every charming, hidden, and iconic location in the Orlando area—and I’m always here to guide you through it.
From location planning to outfit styling and dog logistics (seriously—bring the handler!), I’m with you every step of the way.
Let’s create something beautiful together.
