Postcards from Boca Grande
📍 Boca Grande, Florida

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There’s something timeless about Boca Grande, and every time I try to put it into words, I find myself coming back to the photos. The soft pastel shutters, the late afternoon light on Banyan Street, the quiet rhythm that settles over the island—it’s all a little dreamlike. We were in town for one of my dearest friend’s weddings (more on that in upcoming posts!), but in between the festivities, we managed to soak up a few slow, beautiful days at the Gasparilla Inn. This post is a little peek into those moments—the in-betweens that made the trip feel so memorable.

Most mornings started the same way: a stroller walk down to the Inn Bakery. Brennan happily babbled from her stroller while we sipped our coffee and waved to familiar faces along the way. It’s one of those rituals that feels like it belongs to a slower, more gracious time—everyone unhurried, barefoot or in tennis whites, with a newspaper tucked under their arm. We’d pick up a box of pastries (almond croissants were the clear winner) and enjoy the on the Inn’s front porch while Brennan took in the scenery, thoroughly entertained by the local lizards.

The afternoons were for the Beach Club. There’s no better place to be when the Florida sun is high in the sky and the Gulf breeze is drifting in. We set up under the striped umbrellas while Brennan napped beside us, the Gulf just a short walk away. I love how easy everything feels there—no overplanning, no rush. Just towels, books, snacks, and lots of sunscreen. Brennan even had her first little dip in the sea, squealing every time a wave touched her toes.

In the evenings, we’d stop by BZ’s for a cocktail before dinner. The vibe is relaxed but classic—wicker chairs, warm lighting, and a bar that feels like it’s been there forever in the best way. During these little scapes, my parents would babysit Brennan so we could have a few moments to ourselves. BZ’s always been one of my favorite places to unwind at the Inn, and this visit was no exception. We toasted to a beautiful weekend, and to the feeling that we’re entering a new season—not just of the year, but of life.

Looking back through the photos, I can feel the ease of it all. The simplicity. The way the light lingers a little longer in Boca Grande. I’ll share more from the wedding soon, but for now, these quiet snapshots are the ones I’ll hold onto the most. A few slow, sun-soaked days by the sea, full of tiny rituals that made everything feel special.

Love from Boca Grande,
Katie

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Pool and Sun with Baby
📍 Gasparilla Inn, Florida

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There’s something about being in the water with your baby that makes time slow down in the best way. No schedules, no to-do lists—just sunshine, salty air, and a splashy little sidekick discovering the world one wave (or pool noodle) at a time. This trip was full of firsts for Brennan: her first time dipping her toes into the Gulf, first time “swimming” in the pool with Dad, and first time keeping her sunhat for longer than five minutes (a small miracle). It felt like everything was new and full of wonder—for her, but honestly, for us too.

We spent most of our days toggling between the beach and the pool, letting the rhythm of her naps set the pace—which, in hindsight, might be the secret to a great vacation. At the beach, Brennan was completely mesmerized by the waves. She’d sit on our towels kicking her feet in the sand, squealing every time the water got close. Meanwhile, David and I took turns soaking up the sun, always within arm’s reach of a beach toy or snack. The simplicity of it all—no big plans—was what made it so special. Just being together in the sunshine felt like more than enough.

The pool was a whole new adventure—cool water, bright floats, and the best views of palm trees overhead. David held her while I had a few moments of relaxation and then we’d all float together, Brennan giggling as she splashed. We brought along a few baby swim essentials—a sunhat she actually tolerated, a long-sleeve rash guard, and a shaded float that the Gasparilla Inn generously provided us. Pool time became our daily ritual, the perfect mix of low-effort and high-reward. Brennan loved it, and we loved watching her confidence grow with each little kick.

Of course, traveling with a baby always comes with a few curveballs. There were poolside diaper changes, moments of overtired fussiness, and at least one sunscreen-related meltdown (hers, not mine…though it was close). But there was so much joy in these days. Watching Brennan discover sand for the first time, hearing her laugh echo across the water, and catching little glances between David and me that said, “Can you believe she’s ours?” These are the memories I know we’ll hold onto. Sun-drenched, a little chaotic, and completely golden.

Love from Boca Grande,
Katie

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Baby Girl in Boca Grande
📍 Gasparilla Inn, Florida

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There are some places you visit once, and others you keep going back to. For us, the Gasparilla Inn in Boca Grande has always been the latter. David and I have been coming here for years, drawn in by the charm of old Florida—bike rides under swaying palms, quiet mornings by the water, and a pace of life that makes it easy to relax. It’s one of our favorite places to unwind, and this year felt extra special: we got to bring Brennan for the very first time.

The last time we were here, I was four months pregnant. I remember walking through town wondering what it would be like to come back with a baby. So to return this year with Brennan in our arms—and my parents along for the trip—felt full circle in the best way. We all stayed in the historic main inn with rooms right across the hall from each other, which turned out to be perfect. Brennan loved crawling back and forth between the rooms, soaking up all the attention and turning the hallway into her personal runway.

Our mornings were slow and sweet: coffee in the lobby, pastries from the Inn Bakery, and Brennan waving at everyone we passed in her stroller like she owned the place. The staff at the Inn couldn’t have been kinder—they greeted her every time with a smile, a compliment on her dress, or a quick hello that made us feel right at home.

Naps happened at the Beach Club under striped umbrellas, with the ocean breeze in the background. One of us would hold her while the other snuck in a few pages of a book or sipped something frozen. It’s always a gamble napping a baby on the go, but she did great—especially considering how exciting everything was.

The rest of the day was spent by the water or exploring around the Inn. Brennan was fascinated by the palm trees, the birds overhead, and honestly, just watching people walk by. Everything is new when you’re a baby, which made even the simplest moments feel fun.

In the evenings, we got dressed for celebrating friends, leaving my parents as world-class babysitters. It was so nice to have some room for a mommy-daddy date night filled with great food, fun cocktails, and lots of dancing.

She won’t remember the trip, of course, but I hope it’s the first of many. It already feels like the beginning of something we’ll do again and again—same time, same place, just a little older each year.

Love from Boca Grande,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.