Rachel and Cameron’s engagement session on 5th Avenue South in Naples began with tiny sunglasses, a silk headscarf and one extremely good flower-covered shirt.

Four hours later, they were in Rachel’s mom’s swimming pool while Jay used flash to impersonate the Florida sun after the actual sun had already clocked out.

So yes. We covered some ground 😂

This was technically an engagement session, but Rachel and Cameron were also expecting their first baby!! Instead of separating everything into two different shoots, we photographed this exact, very exciting part of their lives all together: engaged, planning their wedding and about to become parents.

Vintage engagement photos on 5th Avenue South in Naples

Rachel wanted their engagement photos to have a vintage Florida feeling, which made downtown Naples an extremely easy choice.

Fifth Avenue South gave us palm trees, striped awnings, flowering trees, old Florida architecture and those beautifully manicured little corners that somehow make walking down the sidewalk look far more glamorous than walking down a sidewalk has any right to look.

Rachel and Cameron started in coordinating white outfits, but nothing felt overly matched. Her long white dress showed off her bump, Cameron’s shirt was covered in oversized red and green flowers, and then Rachel added the silk headscarf and sunglasses. That one accessory immediately changed the entire look of the photos—which is exactly why I will never turn down an accessory with a point of view!

We walked, wandered through side streets, stopped beneath the palms and used all the colorful little pieces of downtown Naples as we found them. I gave Rachel and Cameron enough direction to keep everything flattering and moving, then let them talk, laugh and be themselves between it all.

That balance is always my favorite. I want you to have beautiful portraits, obviously. I also want your engagement photos to feel like the two of you genuinely spent an afternoon together instead of arriving for an extended appointment with your arms permanently arranged into position.

An engagement session that was also a maternity session

Because Rachel was pregnant, her maternity photos naturally became part of the session too.

There wasn’t a dramatic costume change followed by a completely separate maternity production. Her pregnancy was already visible in everything: the way Cameron rested his hand on her stomach, the way Rachel held her bump while they walked and the tiny moments when they both looked down at the baby.

Their wedding was coming. Their baby was coming. They were standing in the middle of two enormous life changes at once, and I love that these photos will always hold all of it together.

Also, Rachel’s white dress was PERFECT for this. It felt clean and classic against the color of Naples, but still showed off her bump beautifully. Add the scarf, sunglasses and pearl bag, and suddenly we had this slightly retro, extremely Florida maternity-and-engagement situation happening beneath the palm trees.

I was obsessed.

A quick Naples beach stop

Rachel and Cameron love the beach, which makes perfect sense considering they’re getting married at the JW Marriott Marco Island Beach Resort in October with Cocoluna Events!

So, of course, we had to include the Gulf!

Cameron changed into another excellent tropical shirt, because apparently he came prepared with an entire collection, and Rachel swapped out her original sunglasses for a cool red pair, and we headed toward the water. We kept this part easy: barefoot walks through the sand, palm trees overhead and the two of them laughing while the wind attempted to participate. Also…it was super crowded. But you’d never know from the angles I chose!

The beach photographs connect so naturally to what they’re planning for their wedding at the JW Marriott Marco Island. They still feel like Naples, but they also give us that little preview of the warm, tropical atmosphere their guests will experience in Marco Island.

And then we left the beach and drove to Rachel’s mom’s house because Rachel had one more idea.

Poolside engagement photos after sunset

Rachel wanted photographs in her mom’s pool.

By the time we arrived, however, it was getting dark—and bright, playful pool photos become slightly more complicated once the sun disappears.

Fortunately, Jay looked at the lack of daylight and essentially said, “That seems fixable.”

He pulled out the flash and created light that looks like we photographed everything in the middle of the afternoon. The result is this ridiculously fun little poolside world filled with yellow stripes, colorful swimsuits, a matching float, tiny white sunglasses and ice cream that quickly became more of a prop than a snack.

Rachel and Cameron splashed each other, played around on the lounge chairs and eventually got all the way into the pool. Fully committed. No cautiously standing near the edge while protecting the outfits. Into the water they went!

These are some of my favorite photographs from the entire session because they feel so specific to them. They’re colorful, slightly chaotic, very funny and full of the energy that happens once everyone forgets we’re technically taking engagement photos.

They also prove that gorgeous light does not always require a perfectly cooperative sunset. Sometimes it requires Jay, a flash and a very convincing impression of the sun.

Planning your own Naples engagement photos?

Your engagement session can include more than one side of your life.

You can dress up and walk through 5th Avenue South. You can head to the beach, bring the sunglasses you’re currently obsessed with, stop at a place your family loves or jump into your mom’s swimming pool with striped pool floats. You can make it polished, nostalgic, sentimental, completely ridiculous—or all four within the same afternoon!

Rachel and Cameron gave me a full tour of who they are right now, and their photographs feel so much richer because of it.

Now I’m extremely ready to see these two again for their October wedding at the JW Marriott Marco Island with Cocoluna Events. If the engagement session involved three shirts, two headscarves, a beach and an aggressive amount of pool splashing, I have very high hopes for the wedding!

And if you’re looking for a Naples Florida wedding photographer who will happily follow your engagement-session idea from Fifth Avenue to the bottom of a swimming pool, please tell me everything you’re planning!