When couples ask where they should do their engagement session, I usually start with places that already mean something to them. Drew and Trent had plenty of beautiful options, but none of them felt quite right.
Then they asked about Lakeland.
It was home. Their first date happened there. Trent spent much of his childhood on his family’s cattle farm nearby. So I packed my bags and headed south.
Over the next few days, we explored Lakeland, ate at some of their favorite restaurants, played golf at Streamsong, and spent time on the family farm in Bartow.
Lakeland wasn’t just where we took the photographs. It was part of why the photographs mattered.
We stopped looking for the perfect location.
We went home.
Starting the trip at Streamsong felt like full-circle magic since Drew and Trent both worked there back in the day. Knowing how much I love golf, Drew pulled off a miracle and snagged us a 9 a.m. tee time last second.
Safe to say, she made the course look easy. Me? I blew through 12 golf balls in the first four holes.
No official engagement photos were on the schedule for the morning, but my camera came along anyway. It was a morning full of huge laughs, incredible views, and playing one of the coolest courses I’ve ever seen—complete with a few resident Florida swamp puppies.
Streamsong
Texas Cattle Company is where Drew and Trent had their very first date, so there was no question where Day Two of their Lakeland engagement session needed to begin. The staff at the legendary steakhouse was kind enough to let us in before opening hours, giving us full access to the empty dining rooms.
We had an absolute blast capturing candid engagement photos around the rustic restaurant interior and stepping back into the exact booth where their story started.
For the second half of the afternoon, we moved over to Hollis Garden in downtown Lakeland, Florida. The neoclassical architecture, manicured botanical paths, and waterfront views offered a stunning, elegant backdrop for the next chapter of their engagement portraits.
back where it started
Texas Cattle Company & Hollis Garden
For our final day, we made our way out to Trent’s family cattle farm in Bartow, Florida. Trent spent much of his childhood on the land, and as his relationship with Drew grew, the farm quickly became a central part of her story as well. It’s a backdrop tied deeply to family, heritage, and incredible memories for both of them.
The Bartow property is massive. It's the kind of Florida terrain where you definitely need four-wheel drive. We hopped into Trent’s truck and spent the afternoon exploring the sweeping acreage. Listening to them share stories about the land as we drove made capturing their country engagement photos even more meaningful.
We wrapped up the weekend in the open pasture just as golden hour hit, watching the sun drop behind the tree line. It was an unforgettable trip, and I’ll cherish every moment spent photographing Drew and Trent's multi-day Florida engagement session.
Trent's family farm
bartow, florida
