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KATIE KENNEDY

Scenes from the Gasparilla Inn

January 11, 2024

Scenes from the Gasparilla Inn
📍 Boca Grande, Florida

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Gasparilla Inn, Boca Grande, Tuckernuck, Florida, Grand Millennial, Red Dress

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Nestled on the tranquil shores of Boca Grande, the Gasparilla Inn stands as a beacon of timeless elegance and southern charm. This historic hotel unfolds new layers of delight with each visit, making it a perennial favorite. Last Fall, we embarked on another journey to this gem of Florida alongside some of our dearest friends. Here’s a quick recap of our most recent vacation, highlighting lovely scenes, and some pictures to help inspire your next vacation to the Gulf Coast.

Gasparilla Inn, Boca Grande, Tuckernuck, Florida, Grand Millennial

About this Historic Hotel

Stepping onto the grounds of the Gasparilla Inn feels like entering a bygone era. Established in 1913, this historic hotel exudes old-world charm. Its colonial-style architecture, lush gardens, and welcoming verandas transport guests to a time when life moved at a gentler pace. As a member of the Historic Hotels of America, the Gasparilla Inn has seamlessly blended its rich heritage with modern amenities, ensuring each stay is a journey into the past with all the comforts of the present. It’s less than two hours away from Tampa, but it feels like you’ve been transported into the middle of the Caribbean.

Gasparilla Inn, Boca Grande, Tuckernuck, Florida, Mocktail

Mocktails at the Beach Club

One of the highlights of our visit was the leisurely afternoons spent at the Gasparilla Inn’s Beach Club. With toes in the sand and the Gulf breeze whispering through the palms, we indulged in a delightful array of island drinks. Mocktails, for me, would be more accurate, and the Beach Club team most certainly delivered! From refreshing citrus concoctions to tropical fusions, each sip celebrated the relaxed atmosphere that defines this retreat. The Beach Club isn’t just a destination; it’s a sanctuary.

Gasparilla Inn, Boca Grande, Tuckernuck, Florida, Grand Millennial

Endless Interior Charm

Beyond the sun-soaked exteriors, the Gasparilla Inn unfolds a world of interior charm. The lobby, adorned with vintage Floridian décor, expertly curated by Kemble Interiors, invites you to sink into plush sofas and relish the soothing ambiance. From the iconic pink and green color palette to the antique furnishings, every detail is a nod to the Gasparilla Inn’s commitment to preserving its enchanting history. For the interior design obsessed, this hotel’s decor alone is a treat for the senses and a visual feast.

Gasparilla Inn, Boca Grande, Tuckernuck, Florida, Grand Millennial

Tour of the Presidential Suite

During our stay, we received a tour of the Presidential Suite, a lavish haven just off the main lobby. The suite’s views of the islands are awe-inspiring, offering a glimpse into the privileged world of those who’ve graced this distinguished accommodation. Yes, that includes presidents! Elegantly appointed rooms, a private terrace, and personalized service elevate the experience, making it a stay fit for dignitaries and those seeking luxury.


All in all, the Gasparilla Inn isn’t just a hotel, but a destination transcending time. It’s where history mingles with comfort, drinks by the beach are moments of bliss, and every nook tells a story. Our recent vacation to Boca Grande was not just a getaway; it was a reaffirmation that some places, with their enduring charm, become a timeless part of our hearts.

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. 


Filed Under: Boca Grande, Florida, Travel

It’s a Gasparilla Girl!

January 8, 2024

It’s a Gasparilla Girl!
📍Boca Grande, Florida

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Gasparilla Inn, Boca Grande, Tuckernuck, Pregnancy, Maternity, Baby Girl

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David and I have been holding a secret since August!

David and I are thrilled to share that we’re expecting a precious addition to our family this May… A sweet baby girl! The joy that fills our hearts is indescribable as we embark on this journey toward parenthood. From the moment we learned about the impending arrival of our little one, our lives have been filled with a whirlwind of emotions—excitement, wonder, and a profound sense of gratitude. The flutter of tiny kicks and the melody of her heartbeat during ultrasounds have transformed our home with warmth and anticipation.

David’s support and infectious enthusiasm have been my greatest pillars, turning each milestone into a celebration. He’s embraced fatherhood with a joy that is both heartwarming and contagious. As we navigate parenting books and attend prenatal classes, the prospect of guiding and loving this tiny soul together has become a shared dream quickly becoming a reality.

As we navigate these next few months of pregnancy, we are overwhelmed with gratitude for the support, love, and encouragement that surrounds us. May is not just a month on the calendar; it’s a chapter in our lives that will begin a beautiful and sleep-deprived adventure into parenthood. Our hearts are ready, our home is getting prepared, and our souls are brimming with excitement as we eagerly await the arrival of Baby Girl Kennedy this May.

I can’t wait to give you more details along the way as we experience this new chapter stage of my life.

Love from Boca Grande,
Katie and David

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. 


Filed Under: Boca Grande, Florida

Ins and Outs for 2024

January 5, 2024

Ins and Outs for 2024
📍 Boca Grande, Florida

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Ins and Outs, 2024, Trends, Gasparilla Inn, Boca Grande, Florida

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Happy Friday! How is the first year of the New Year treating you? After a relaxing New Year’s Day, I’ve been at full speed to catch up on work. It’s the crux of having a full week away from the office. Although I rang in 2024 with more laid-back festivities, the New Year is one of my favorite holidays. Like opening up my brand new planner, it feels like a fresh start and has room for almost limitless opportunities. It’s also a time to reflect on the growth and changes I hope to make in the 365 days to come. I have loved reading about people’s Ins-Outs over the past few days and wanted to share one more for good measure. Here’s a quick recap of my trends for 2024.

Ins and Outs, 2024, Trends, Gasparilla Inn, Boca Grande, Florida

Reading Every Night Before Bed

As a kid, I was a ravenous bookworm, reading until I couldn’t keep my eyes open anymore (often under the covers with a flashlight). Each year, I have a goal to get back into reading. I start strong, but right around mid-summer, it ultimately gets derailed. Maybe my number is too lofty. I mean, 50 through a whole year sounds like nothing. David suggested I make a goal of 24, as in 2 books per month. That’s what I have penciled down, with hopes to read many more.

More Frequent Moments of Self-Care

I almost criminally procrastinate on self-care. Oh, I don’t need a haircut. I’ll get a pedicure closer next week. A massage seems like a frivolous spend. The list goes on. This year, I want to find opportunities to treat myself while making daily activities a spa-like experience. First on my list? That haircut! I’m making an appointment at a salon in Manhattan to refresh my hair and feel a little pampered.

Jazz Playlists with Morning Coffee

This is something that David and I started in 2023. I can’t wait for it to continue into 2024 and beyond. It’s nice to start each morning with a pre-work ritual. David, an early riser, makes a fresh pot of coffee to lure me out of the warm bed. We listen to light jazz, prep for our day, and discuss ideas we’re working on. In truth, it makes me feel like such a power couple! Consider it our tiny moment of zen that we’ve both come to know and love.

Ins and Outs, 2024, Trends, Gasparilla Inn, Boca Grande, Florida

Mindless TV Watching

I love a little background noise while working on my computer all day. Just pop on a favorite comfort show, and I feel inspired to be a little more productive. Sounds great, right? The problem happens when I plant myself on the couch and continue watching that show into the evening. This year, I would like to limit my TV time, focusing on making it a shared experience with David. We don’t have to miss the newest movie or the hottest TV show, but we want to make our habits more intentional.

Working Through My Lunch Break

With a remote job and hobby that takes place almost entirely online, my screen time consumption has been way up. This year, I want to focus on giving myself mini breaks away from the screen, namely, when I’m eating lunch and taking my dog, Tripp, for a walk. These tiny moments away from technology will help me connect with the present, decompress during a stressful day, and support my eye health. Besides, I’m sure Tripp would be much happier if my focus were on him. That work email can wait a few minutes.

Cluttered Closets and Wardrobes

I’ve already laid a lot of groundwork to declutter the spaces in my life. Moving across the country will force you to look hard at what you own. Thinking well into 2024, I want to purge the clothes that don’t fit and what I don’t wear to leave room for a perfectly curated capsule collection. Your 30s is when you can nail down your personal style. I’ve been enjoying timeless silhouettes in monochromatic colors to optimize their versatility. Cheers to multifunctional pieces that will last me a lifetime!

Like I said, I love reading about people’s Ins and Outs. It is a fun and more approachable pivot from the dreaded resolutions that ultimately don’t last more than a few weeks. No matter what’s made your list this year, I hope you can maintain healthy boundaries and find little ways to make the day brighter through 2024.

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. 


Filed Under: Boca Grande, Florida, Travel

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