Lauderdale-By-The-Sea: Perfectly Imperfect Coast - City #5

Lauderdale-By-The-Sea marked a fifth city stop, technically a town, sure, but with its own post office, which feels official enough for blog purposes.

South Florida Food Tours turned out to be the right call. The guide stitched the area together with equal parts history and hometown pride, the kind of storytelling that makes each bite taste like it belongs. A standout stop: a small Jamaican spot tucked right in the heart of downtown, called “Alexandra’s.” Alexandra greeted guests at the door with a bright smile and a soft Jamaican lilt: “Welcome, please, come on in.” The jerk chicken was the kind of good that doesn’t just end a meal; it plants the seed for a return trip.

Lauderdale-By-The-Sea stays low to the ground on purpose, a true low-rise community with a height limit that keeps the sky feeling big. With only about 6,000 residents, an “old Florida” ease lingers, as if the modern world agreed to whisper for a while. The beaches were clean, but the wind arrived with an attitude, pushing salt air in sharp gusts and roughing up the water into white-capped drama. Out along the shore, the broken pier stood like a reminder that nature always gets the last word. Damaged in a recent hurricane, the pier faces an especially tricky rebuild because of the coral reef below. Privately owned and expensive to repair, the structure is also tangled in legal and financial hurdles. Rebuilding requires approval from multiple agencies, including the Army Corps of Engineers and the Department of Environmental Protection, and the process is expected to take several years. Until then, the scene looks perfectly imperfect.

For views, Aruba Beach Café stole the show. When the wind isn’t quite so relentless, the doors open and the place becomes a front-row seat for ocean watching, live music in the background, good food on the table, and that steady rhythm of waves doing what they’ve always done. The “Aruba Ariba” adds a playful tropical curveball: vodka, rum, passion fruit syrup, crème de banana, and a bright mix of orange, pineapple, and cranberry juice, vacation with its volume turned up.

A perfect ending to a weeklong trip: sun on shoulders, sand in inconvenient places, laughter that carried late, and (in full honesty) a little too much drinking. Thanks for the memories, Florida.

Raised Bridges and Restless Waters - Boca Raton City #4

 Boca Raton was city number four, and it made a polished first impression. This is city 4 of 4 that I don't remember visiting. This is a town that clearly cares about appearances The town just feels clean. It is meticulously kept, and spotless at every turn, as if every sidewalk and palm tree knows its role. The rhythm of the city felt coastal and unhurried, shaped by fishermen casting lines and beachgoers drifting toward the sand, alongside a steady stream of tourists drawn by the promise of sun and sea.

One of the most intriguing features was the series of drawbridges crossing the Intracoastal Waterway. They felt almost theatrical in their timing and presence. At one point, a bridge tender’s voice boomed sternly over a loudspeaker, scolding an unsuspecting jogger who had chosen the worst possible moment to cross, the bridge rising beneath his feet. Oblivious to the warning at first, the jogger scrambled off as the tender urged him to clear the bridge quickly, adding a moment of unexpected drama to an otherwise tranquil scene.

The visit came with moody weather. Rain drifted in and out, and the skies couldn’t quite make up their mind. Sudden gusts of wind swept through the streets, and the Atlantic Ocean looked restless and angry, its waves crashing with purpose. Even so, the energy of Boca Raton remained vibrant. The city felt alive, expressive, and inviting, proof that sunshine isn’t the only thing that gives a place its charm.

Despite the unpredictable weather, Boca Raton was fun to explore, full of character and coastal flair. It’s a destination that leaves a lasting impression, and one I wouldn’t hesitate to return to, ready for more moments, more memories, and perhaps a little more fun in the sun.

 

Deerfield Beach: Sun, Salt, and Simple Pleasures City #3

 City #3: Deerfield Beach

Deerfield Beach was city number three, and from the moment I arrived, it felt like a place that didn’t need to shout to be noticed. I have never been here before, so this is 3 of 3 cities that I have never visited. Laid‑back and quietly confident, the city holds more life than it first appears, nearly 90,000 people tucked between ocean blues and palm‑lined streets. It’s known for its pristine Blue Wave beach, its internationally recognized fishing pier, and an atmosphere that invites visitors to slow down and stay awhile.

For just two dollars, you can stroll the length of the pier, listening to the rhythm of waves beneath your feet. Four dollars buys you a chance to fish, and sometimes, a story worth remembering. One local fisherman proudly showed off a king mackerel he had just caught, so massive it refused to fit inside his oversized cooler, as if even the fish here resisted containment. The beachfront stretched endlessly in both directions, soft sand meeting open sky. In the distance, a lighthouse stood watch about two miles away, steady and timeless against the horizon.

Pelican Harry, my unofficial name for him, was perched on the pier as if it were his personal lookout. He let me get close, close enough that I nearly could have touched him, yet he never shifted or flinched. He wasn’t camera shy in the slightest; if anything, he seemed to welcome the attention, posing patiently as the waves rolled beneath us. Calm, unbothered, and entirely at ease, Harry felt like just another local, perfectly content, soaking in the slow, steady rhythm of the day.

The parks throughout the area were spotless, lush, orderly, and clearly well cared for. You could see where the city invests its pride. While I couldn’t help but wonder about the property taxes, the answer was right there in the manicured green spaces and welcoming public areas that made the city feel loved.

Even when scattered rain showers passed through without warning, the weather remained gentle and forgiving. Deerfield Beach didn’t seem bothered by imperfection; it embraced it. As evening settled in, pizza places appeared on nearly every corner, each promising comfort and familiarity. Ending the day with pizza and a cold beer felt exactly right, the perfect close to a day that asked nothing more of me than to relax, observe, and enjoy.

 

Where the Waves Set the Pace - Pompano Beach City #2

 Pompano Beach, Florida: City #2.

Pompano Beach, Florida marked the second city on the 60‑city tour, and it immediately leaned into that laid‑back coastal vibe. I had never been to Pompano Beach before, making it two out of two cities so far that were completely new to me. The Wyndham Resort would be home for the next seven days, and it felt like a solid choice from the start. The spacious suite came with not one, but two balconies, one offering a glimpse of the endless blue Atlantic Ocean as it shimmered between two towering timeshare buildings, and the other overlooking the glassy, slow‑moving waters of the Intracoastal Waterway. Warm ocean air drifted through the open doors, carrying the faint scent of salt and sunscreen. It felt like there were more resorts here than palm trees, a clear sign that this town knows exactly how to cater to vacation mode. Arriving on a weekend meant weaving through clusters of sunburned tourists and beach bags while figuring out which nearby spots were easy to reach on foot, but that’s all part of the beach‑town rhythm.

The pool area quickly became a favorite retreat. The water was cool and inviting, a welcome contrast to the thick Florida heat, and the hot tub quietly bubbled nearby. It wasn’t overrun with kids, which made the space feel calm and unhurried. Patches of shade offered relief from the relentless sun, making it easy to settle into a lounge chair and lose track of time. Just a short block away, the beach delivered exactly what you hope for, warm sand underfoot, rolling waves, and a steady ocean soundtrack that seemed to wash the day clean. Sitting back and listening to the waves crash and retreat against the shore was deeply tranquil, the kind of sound that slows your breathing without you even realizing it.

That evening wrapped up perfectly with a quick stop at the grocery store to pick up a few essentials, followed by dinner at a cozy, hole‑in‑the‑wall Italian restaurant. The food was simple, comforting, and full of flavor, the kind of meal that feels especially satisfying after a sun‑soaked day. Unpretentious and delicious, it was the perfect ending and made Pompano Beach feel easy, welcoming, and surprisingly effortless to settle into.

Fort Lauderdale: Canals, Sunshine, and Vacation Mode City #1

Fort Lauderdale has a pretty cool backstory. It started out as a military outpost during the Second Seminole War back in 1838 and was named after Major William Lauderdale, whose expedition built forts along the New River. Fast-forward a whole lot of years, and this once-quiet winter escape has grown into what people now call the "Yachting Capital of the World."

One of the first things that makes Fort Lauderdale stand out is all the water. The city has more than 300 miles of navigable waterways, with 165 miles running right through the city itself, which is why it’s often called the "Venice of America." It really does feel like boats and canals are part of everyday life here.

It’s also a huge spot for boating and cruising. Fort Lauderdale is home to more than 50,000 registered yachts, and Port Everglades is the third-busiest cruise port in the world. Between the massive ships, marinas, and endless boats, it’s easy to see how the city earned its reputation.

Fort Lauderdale also has a legendary spring break history. Back in the 1960s, the cult-classic movie Where the Boys Are helped put the city on the map as the original wild spring break destination, drawing huge college crowds every year. These days, though, the vibe has shifted a lot more toward family-friendly beach town than party capital.

And of course, the weather is a big part of the appeal. With an average temperature of 75.5° F and more than 3,000 hours of sunshine each year, Fort Lauderdale is basically built for warm-weather escapes. Snow is almost unheard of here, it’s only happened once in recorded history, on January 19, 1977.

Flying into Ft. Lauderdale was such an easy start to the trip. From the airplane window, the view was gorgeous, bright blue ocean water crashing against strips of white sand, like a postcard come to life. The airport itself was small and super easy to get through, which made grabbing a rental car quick and stress-free. After that, it was an easy drive to the hotel with barely any traffic, which honestly felt like the perfect way to kick off a full week of vacation. If the rest of the trip starts this smoothly, I’m already off to a great beginning.

A Birthday, a Boarding Pass, and the Year Ahead

 Today, the calendar turns and so does my life

Day one of a year-long odyssey: sixty cities, sixty candles, sixty stories waiting to unfold.
With a flight to Ft. Lauderdale, the horizon opens wide, inviting adventure and possibility.

Morning greeted me with three phone calls and a constellation of messages
Each one a gentle reminder that I am held in the orbit of love and friendship.
How fortunate I am, surrounded by voices that echo care,
Beginning this journey not in solitude, but in the company of cherished hearts.

As I step into this milestone year,
I carry gratitude like a passport, stamped by kindness and connection.
The world awaits, and I move forward
Not alone, but sustained by the warmth of those who walk beside me.