Pool and Sun with Baby
📍 Gasparilla Inn, Florida

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Tee || Pareo || Bikini Top || Bikini Bottom || Flip Flops || Tote Bag || Sunhat

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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Dress & Baby Girl Dress

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

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Back in the Sunshine State
📍 Boca Grande, Florida

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Top || Shorts || Sandals || Clutch || Earrings || Lip Color

It had been a year and a half since my last visit to Florida, and this time, I genuinely felt like a tourist. The palm trees, pastel houses, salty breeze—it was all familiar, but it didn’t feel like home anymore. It felt like a mini escape in the best way. Slower mornings, sunnier afternoons, and that easy, no-plans-needed kind of energy Florida does so well.

We started the trip in St. Petersburg, the city where David and I met, got married, and lived for years before our move to NYC and Connecticut. It was our first time back with Brennan, which made every little moment feel more special. We walked through our old neighborhood, had coffee at our favorite spot downtown, and caught up with friends who have been with us through so many chapters. There was a comforting sense of familiarity—but this time, we were visitors, not locals. We noticed things we never used to, took our time, and didn’t mind moving at a slower pace.

After a quick overnight in St. Pete, we drove south to Boca Grande for a dear friend’s wedding at the Gasparilla Inn—our favorite place to completely unwind. The Inn was as charming as ever, and the island felt like something out of a Slim Aarons photo: timeless, bright, and beautifully relaxed. Between wedding events, we made the most of our downtime with beach club lunches, frozen cocktails, long stroller walks, and sunset watching that felt like a daily ritual.

Of course, traveling with a baby changes things. Our bags were heavier, naps dictated our schedule, and nothing happened quickly—but it also made the whole trip feel even more meaningful. Watching Brennan splash her feet in the Gulf, giggle at lizards darting by, and nap peacefully under a palm tree is a memory I’ll keep tucked away for a long time. It felt like the beginning of a new tradition.

This wasn’t our usual Florida trip, and I think that’s what made it so memorable. There was no rushing, no big agenda—just a chance to revisit some of our favorite places with fresh eyes (and tiny hands in tow). Sometimes you need a little distance to appreciate a place all over again. Florida, you still know how to work your magic.

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.