KATIE KENNEDY

An Overnight at the Vinoy

An Overnight at the Vinoy
đź“Ť St. Pete, Florida

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One last blog post from the Sunshine State! You’ve followed along on my Gasparilla Inn adventures, but there’s still one more leg to share, Brennan’s first visit to St. Pete! For those of you who are newer followers, I am a born and raised Floridian, calling St. Pete home for many years. It’s where David and I met, got married, and holds so many incredible memories. Although we are beyond happy with our move to Connecticut, we still miss a few things about this little corner of Florida. Apart from family and friends, the Vinoy Hotel is one of those things that we miss. Before heading down to Boca Grande, we decided to stay at this historic hotel for a quick overnight, and it was such a great decision! 

The Vinoy has been a fixture in downtown St. Pete for nearly a century, and stepping inside always feels like a return to something familiar. Built in 1925, it was originally a seasonal resort for the well-to-do escaping northern winters. Over the years, it’s welcomed celebrities, baseball legends, and generations of Florida families. After falling into disrepair during the mid-20th century, it underwent a major restoration in the 1990s and has only become more beautiful with time. Today, it’s part of Marriott’s Autograph Collection and blends historic charm with thoughtful modern touches—ornate ceilings, terrazzo floors, and that unmistakable blush pink exterior that always makes me smile.

We checked in and went straight into vacation mode. The pool was our first stop, and even though the setting has been refreshed over the years, it still holds that same relaxed energy I remember growing up. Brennan was taken with the shallow end, splashing and squealing excitedly while we caught up with friends under a big striped umbrella. Later that afternoon, we met one of our dearest friends for lunch at Paul’s Landing, the hotel’s breezy waterfront restaurant. I had a frozen Congelado (so good on a warm day), and we watched boats bobbing in the harbor while Brennan people-watched from her high chair like a seasoned local.

The next morning, we were all up early and decided to take a family walk along the bay. The light was soft, the breeze was gentle, and there’s just something about those quiet, early hours in St. Pete that feels restorative. Brennan loved taking in the boats and birds, and we took our time soaking in the views and crisp morning air. Afterward, we grabbed coffee from Lottie and found a spot on the Veranda patio to sit and relax. It was the perfect little pause before heading down for breakfast by the pool. Dining poolside felt like such a treat—Brennan was content in her high chair, we had a shady table with a view, and the Bloody Marys were as good as I remembered. It was one of those simple, unhurried mornings that reminded us why we love this hotel so much.

It was a quick trip, but exactly what we needed. The Vinoy will always be one of those places that feels like a chapter of our story. I’m so glad we carved out the time to visit, especially with Brennan in tow. Watching her take in the same sunshine, poolside giggles, and waterfront views I’ve loved for years was pretty special. If you ever find yourself in St. Pete, this spot is absolutely worth a stay—or at the very least, a slow morning coffee on the veranda.

Love from St. Pete,
Katie

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Black Tie Wedding by the Sea

Black Tie Wedding by the Sea
đź“Ť Gasparilla Inn, Florida

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After a few magical days soaking in the laid-back beauty of Boca Grande, our time on the island ended with the kind of evening you wish you could relive over and over again. A black tie wedding at the legendary Gasparilla Inn—equal parts grandeur and charm—was the perfect final chapter. There’s something truly special about an event where every detail feels meaningful, and every moment feels suspended in time. The swaying palms, the golden light, the hum of live music floating through the air—it all created a setting that felt both cinematic and deeply personal.

We were in town to celebrate the wedding of two dearest friends. The bride and I met years ago at a blogging event in SoHo, back when I had just moved to New York City. It was one of those rare, instant connections—the kind of friendship that begins easily and grows quickly. Over time, our partners formed an equally strong bond, and together we’ve shared so many unforgettable moments: late-night dinners in the city, long weekends in beautiful destinations, and more laughter than I could ever count. To witness their love story unfold and be there as they said “I do” was nothing short of an honor.

What stood out most about the wedding—aside from the sheer joy in the air—was the attention to detail. Everything felt effortless yet incredibly thoughtful. The reception was held on the Inn’s sweeping lawn, framed by towering palms and that unmistakable old Florida architecture. There was a distinct sense of place: cane furniture with monogrammed linens, citrusy cocktails, floral arrangements that felt handpicked from a garden rather than a catalog. It was elegant without being fussy, refined without ever losing its warmth. The setting sun casting a soft glow on the façade of the Inn made it all feel like something from a Slim Aarons photograph.

Since this was my first official black tie event (surprisingly!), I knew I wanted a look that felt classic and versatile. I chose a one-shoulder black satin maxi dress that skimmed the body just so—understated yet striking. I can already imagine wearing it again for future weddings or formal events, which is always a win in my book. I paired it with simple yet comfortable block heels from Margaux, which gave me height without sacrificing dance floor stamina. These heels stayed on the entire night of dancing and twirling. My handbag was a round Clare V. raffia handbag—a nod to the tropical setting, with just the right amount of texture and whimsy. Hair slicked back, gold jewelry, and a warm breeze—it all came together beautifully, without ever feeling overdone.

I have to give a little credit where credit is due: David looked incredible. There’s something about seeing your partner dressed to the nines that just hits differently. His tuxedo, a sharp black number from J.Crew, fit him perfectly and matched the tone of the evening. Instead of traditional dress shoes, he wore Rothy’s loafers—which, fun fact, I found at a thrift store during one of my treasure-hunting weekends. They’re sleek, sustainable, and unexpectedly polished. His whole look was understated but refined, and he carried himself with that relaxed confidence I always admire.

The entire weekend was filled with beauty, laughter, and moments that felt like little treasures. But that final night—standing under strings of lights, surrounded by dear friends in tuxedos and gowns, most dancing barefoot by the end of it all—was something I’ll carry with me for a long, long time. The Gasparilla Inn has a way of making time feel slower, more intentional, more beautiful. And as we packed our bags the next morning, I couldn’t help but feel grateful—not just for the memories made, but for the people who make them so special. We’re already dreaming of our next visit.

Love from Boca Grande,
Katie

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Beach Club Celebrations

Beach Club Celebrations
đź“Ť Gasparilla Inn, Florida

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There’s something so special about kicking off a wedding weekend with a welcome party—and my dear friend’s was truly unforgettable. Held at the Beach Club at the Gasparilla Inn, the evening felt like the perfect blend of elegant coastal charm and laid-back celebration. Set right on the water, with wide open views of the Gulf of Mexico, the entire party felt bathed in golden light and sea breeze. It was the kind of setting that made you instantly exhale and just be—present, joyful, and ready to celebrate one of the most important weekends in our friend’s life.

As guests arrived, we were greeted by soft music, signature cocktails, and the gentle sound of waves in the distance. The space was styled beautifully—effortlessly chic with shell-inspired details tucked throughout. From the shell place cards to the creamy white florals and rattan accents, everything tied back to the beach in a subtle, sophisticated way. There were so many little touches that felt thoughtful and intentional, and I know how much care went into creating a space that felt celebratory but still true to the Inn’s coastal, unfussy style.

For the evening, I chose a pale blue dress from Tuckernuck that struck the perfect balance between playful and elegant. The high neckline and tailored silhouette kept things polished, while the feather-trimmed sleeves added a whimsical, celebratory touch that felt just right for a beachfront soirée. I paired it with nude heels from Sarah Flint, a woven clutch, and a pair of classic pearl earrings—an effortless nod to the natural beauty of the setting. David wore a lightweight knit polo from Octobre by Sézane, paired with slim dark olive trousers. It was a warm, breezy night, so his blazer didn’t make it into the final look, but he still looked every bit the part with a refined yet relaxed style that complemented the evening’s laid-back glamour.

This night set the tone for the entire weekend—it was relaxed, joyful, and full of love. There was so much laughter, a little bit of happy crying, and more dancing than I expected (always a good sign!). While I’ll be sharing more from the wedding day itself in an upcoming post, I wanted to give this evening its own little spotlight. There’s something about those first moments of a wedding weekend that feel extra tender, full of hope and love and anticipation. And this one, set by the sea with salty air and starry skies, was simply unforgettable.

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.