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KATIE KENNEDY

Travel Daydreams for 2024

January 12, 2024

Travel Daydreams for 2024
📍 Boca Grande, Florida

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Gasparilla Inn, Boca Grande, J. Crew, Travel, Grand Millennial, Coastal Living

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I shared some incredibly wonderful news earlier this week that will likely slow down travel in 2024. Trading a few trips and adventures for Baby Girl Kennedy seems like the deal of a lifetime! Still, travel will always be on my mind! Even though I’m not sure what this year has in store, I look forward to new and old destinations. Here’s a look at six places I daydream of visiting in 2024.

Newport, Rhode Island

June will mark not just the arrival of summer but a milestone as we embark on Baby Kennedy’s inaugural journey. What better place to introduce her to the wonders of travel than Newport, our beloved New England haven. This seaside town isn’t just a destination; it’s a tapestry of history and coastal beauty that we can’t wait to share with our upcoming family member.

Gasparilla Inn, Florida

Returning to the Gasparilla Inn in Florida is like revisiting an old friend, and this time, we’re transforming it into a family affair. Our stay is motivated by a friend’s wedding, and we’re turning the celebration into a multi-generational vacation by inviting my parents along. With its timeless charm and the promise of sun-soaked days on the Gulf, we hope Baby Kennedy will love this slice of paradise as much as we do!

The Claremont, Maine

The Claremont in Maine has lingered on my travel bucket list for several years. This year, I hope the drive to this retreat becomes a reality. Nestled in Arcadia, we plan to make the journey as memorable as the destination, with a pit stop at the White Barn Inn in Kennebunkport. From exploring coastal charm to relaxing poolside in the heart of Maine, The Claremont promises a blend of adventure and tranquility.

Hamilton Princess, Bermuda

If our wanderlust extends beyond domestic borders, Bermuda is the top choice, especially the Hamilton Princess. With its pastel hues, pink-sand beaches, and a charm that dances between British elegance and island ease, Bermuda is the epitome of effortless travel. The island beckons with the joy of introducing our little one to a world beyond her own.


In the tapestry of our 2024 travels, each destination represents not just a pin on the map but a chapter in our family’s story. Our travel dreams unfurl with the promise of adventure, connection, and the creation of memories that will linger long after the suitcases are unpacked. As the year unfolds, so will the pages of our travel diary, narrating the tales of exploration and the joy of discovering the world anew.

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: Travel

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

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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