This year, winter came, and she was an unkind, leggy beast that left me in her dreary, shivery wake, weak and weary. Just one day after my grandma’s 91st birthday, hours before the birthday party we were all getting ready to happily attend, she was rushed to the hospital and a few days after that, she peacefully bid this world farewell. Sure, 91 is an incredibly long life, but grandma made it feel like she wasn’t ever going anywhere. She was sharp, fashionable, funny, full of vim and vigor. It’s never easy to say goodbye, even when it’s a graceful exit like hers, and it wasn’t easy. Sadness always weakens my immune system and shortly after grandma’s passing, I became incredibly ill and caught pneumonia. This took me out for, honestly, a couple of weeks in total, causing me to have little energy to distract myself from my sadness. Not to mention, we endured a polar vortex and I for one am a desert dweller at heart. I hate to bum anyone out, as I typically run on optimism, but, life happens and we need the dark to appreciate the light. I needed light. I didn’t just welcome spring, I needed spring.
I preface this post with this because it illuminates the purposes of this trip I’m about to detail: escapism, fun in the sun, and quality time together to have fun and be on “island time.” We hadn’t taken a trip just the two of us since the previous year’s spring break, so we were overdue. Al and I always have fun together, even at home doing chores, but one of the reasons I truly fell for my adventurous man is because of how well we traveled together from the very beginning when we were young, penniless bucks. Our trips together recharge my battery and equip us with a reserve of glittering memories. At first we were considering somewhere in the Caribbean, but we were late to the booking game and decided to head somewhere in the U.S. that wouldn’t be a logistical fiasco and would still offer us a tropical vibe. Key West fits that bill, and though I have been a few times, to me, it’s a destination worth revisiting especially with this vacation agenda. Neither of us had ever spent any real time in Miami, so we decided to spend our first two nights in the heart of South Beach before renting a car for the day to road trip down to Key West for the remaining three days of our trip. Below are highlights and favorites of this sunny, coconut flavored, true Vacation.

Trip itinerary:
- South Beach, Miami for two nights, staying at Hotel Breakwater in the heart of Ocean Drive
- Key West, FL for three nights, staying at the quaint and convenient Tropical Seascape Inn just off Duval Street
South Beach nightlife:
We flew into Fort Lauderdale, as it was cheaper, and got a Lyft from FLL to South Beach, an easy 30 minute ride. The sun had set so we were greeted by Ocean Drive’s neon Art Deco signage and the relentless vibrations of both DJs pumping club anthems from the indoor/outdoor restaurants and lounges lining Ocean Drive and attention-seeking Ocean Drive drivers competing for who can blast their music loudest. I knew South Beach was notorious for its party vibe, but I didn’t genuinely appreciate that known fact until I lived it. I’m a Vegas girl at heart and I can honestly say, I think South Beach is more wild than Vegas. Al and I posted up at an outdoor table at Havana 1957, our hotel’s restaurant, where we engaged in cocktail and appetizer sampling and one of the most amusing South Beach pastimes: people watching. A river of humanity flows up and down the sidewalks of Ocean Drive, the iconic main boulevard parallel to the equally iconic beach lined with fruit loop colored lifeguard huts. Bachelorettes, bachelors, spring breakers, elderly couples, families, and armies of girls trips flood the scene. It’s a ceaseless flow that moves to the rhythm of Latin beats and pretty hostesses beckoning their prey, the air ripe with mint, rum, and sugarcane, and a neon rainbow of flashy and questionable fashions. Al and I quickly learned that Ocean Drive is absolutely the place to go for amusement, but not for authentic or notable dining. The drinks were decent along Ocean Drive, albeit, insanely expensive. We did a little make- your-own bar crawl, which ultimately ended in my personal demise the next morning. The bar/club literally next to our room, which unfortunately was on the first floor and the noisiest room we have ever stayed in, turned out to be one of our favorite bars on Ocean Drive- fantastic music, entertainment galore in the forms of bachelorette and bachelor parties and European families hitting the dance floor altogether, and they surprisingly made a fabulous extra dirty martini, of which I had one too many for this overly eager spring breaker. I believe the club was an extension of Havana 1957. If you go to South Beach and hit up Ocean Drive, you won’t be able to miss it, it’s in the heart of the action and has a DJ on a stage and fountains running down the middle of its living wall lined open air courtyard. Al and I ended our super late first night on the beach, toes in the sand, giggling at other vacationers who had bravely decided to skinny dip. Bottom line on South Beach nightlife: it’s a party. We didn’t attempt to go to any actual clubs, but our Lyft driver told us the clubs don’t heat up until 2 AM, and most people don’t go out until 1 AM at the earliest. He said most people aren’t finishing their evenings until 7 AM. And I thought Vegas was wild.




Little Havana and Wynwood:
Though I got off to not my finest of mornings the following day, I was able to get myself together at a reasonable hour so we could tour a couple sights of interest: first stop, Little Havana for authentic Cuban food, and a mini Cuban culture immersion. Then, on to Wynwood for street art admiring and strolling the hip neighborhoods. Little Havana was not exactly what I was expecting, it’s a bit more spread out than I had imagined, but it’s still worth a stop! We ate at Versailles, which is one of the oldest, supposedly most authentic Cuban restaurants in Little Havana. I learned on this trip that Cuban food isn’t my favorite cuisine, but I still enjoyed the experience of this restaurant and the service was fantastic. I ordered the Cuban paella, while Al ordered the Cuban sampler plate which kept him overly satiated until 9 PM. After Versailles we took a quick Lyft to Calle Ocho, the famous street of Little Havana where we first stopped at Ball and Chain for Coronas and amazing live salsa music. We then walked up and down Calle Ocho, which is a remarkably un-American sensory experience. Between the serenade of chickens and roosters and the fragrance of coconut and fresh fruit stands on every corner, and then Domino Park clad with weathered faces and the delicate clinking of strategic tile placement, Calle Ocho feels like what it is: a little Havana, a trip beyond borders.




We got another Lyft to head to Wynwood, our first stop: the Wynwood Walls. Upon entrance into Wynwood, the vibe could not be more of a stark contrast to Little Havana, which was neat for us because we had such a diversified, touristic day. Wynwood is hip, trendy, arty, and young. Wynwood Walls is an indoor/outdoor art “museum” full of whimsical, vibrant wall art as well as avant- grade collections of sculptures, paintings, and collectibles produced by various artists across the world from various time periods. It is absolutely worth checking out! After Wynwood Walls we strolled the streets a bit until we got to the Wynwood Marketplace, an outdoor market with endless rows of tented vendors selling clothing, jewelry, art, food, and beverages. In the center of the marketplace is a loud indoor/outdoor bar. We strolled and tried on various treasures before deciding the sun was a little too ruthless and our bellies were still a little too full from our authentic Cuban cuisine experience, so we headed back to South Beach for a small siesta on the beach. The beach is lovely, albeit, napping was a challenge with the party that is South Beach. Between three different girls trips surrounding us and then two couples who came stumbling onto the beach just beside us, the entertainment was unavoidable and distracting. We caught a creamy, dreamy, pastel sunset on the raucous beach before heading back to the hotel.










Dinner in South Beach:
We were both still licking our wounds from our far too lubricated first evening out, and we were also in need of a reprieve from the feral amusement of Ocean Drive, so we hunted for a quiet, sophisticated Italian restaurant about a mile off the main drag. We walked to Macchialina, which looked adorable and charming and smelled divine, but sadly they were entirely booked up. We walked a couple blocks past Macchialina and found a quiet, bistro lit, white table clothed Italian spot called Da I Frasca and decided to take a chance. They sat us out on the peaceful patio, candlelit, and tented with a living wall and Italian regulars, one accompanied by his adorable Italian dog. This place was heavenly. The pasta was homemade, the wine list was extensive, and the service was impeccable. We highly recommend!

Road Tripping from Miami to Key West:
Al and I have done the trip from Fort Lauderdale to Key West via convertible before, and we remembered it fondly. The ride is flat and easy, but such a wondrously watery visage! For much of the ride, you are sandwiched between turquoise waters stretching as far as the eye can see. The road and water are nearly on the exact same plain, so it creates the illusion that you’re riding atop water, which is a welcome trip in our book. We rented a newer Mustang convertible through Hertz at the Miami airport and then hit the sandy road. Getting out of Miami takes about 20-30 minutes of highways, then you’re on double lane roads flanked by dense mangrove swamps and cerulean seas. We drove for about an hour and a half before stopping in Key Largo for lunch. I had originally planned for us to go to a sleepy hole-in-the-wall called Mrs. Macs, but when we drove past it, it looked a bit more sad than charming. We did a quick search for waterfront lunch spots and I liked the looks of Skippers Dockside. We took a chance as it is kind of set in an unassuming neighborhood off the coastal highway, but this place is one we would absolutely recommend and love to return to for lunch! It had a circular outdoor deck that hugged a canal clad with a bevy of nautical vessels, from pristine and stately to vintage and rusty. We enjoyed the local catch as we were serenaded by an incredible live musician crooning classic rock staples that inspired massive waves of nostalgia for us both. The food, service, and ambiance were a Floridian vacation lunch at its finest!

After lunch we headed to John Pennekamp State Park for some sea and mangrove maze kayaking. This was a peaceful way for us to burn off a little bit of our hefty lunch and to soak up some Florida sunshine in the first underwater park established in the U.S. The park is well appointed with public restrooms and showers, a gift shop with aquatic gear for rent and purchase, and a sweet little visitor center with a huge aquarium where you can learn about the ecosystem and who it is home to. We opted for the short kayak loop, as we still wanted to stop at a couple more places along our route, and this was the perfect amount of time for us to get a small dose of exercise and to take in the mangrove landscape. The water isn’t that cerulean dream color that many Florida beaches boast. Instead, it was a dark emerald color, but still quite clear. I kept looking out for marine life, but sadly all we saw was a great deal of tall, underwater grass. My favorite part of the loop was when we got out to an open stretch of ocean after kayaking the back marshes, and we took a little break to admire some boats anchored nearby, the water gently lapping against the planks.
A little briny and sunkissed, we hopped back in the convertible to head to our next stop: Islamorada. We were hoping to find the inn where Bloodline is filmed, which is called Mooring Inn and Spa. We did locate it, and it looked gorgeous and charming, however, it was clearly marked as private property and cautioned no trespassing, so we obeyed and admired from the car. We had planned on doing a full stop in Islamorada for the artist village, but decided against it so we could make better time for Key West check-in. We did have to make a stop, however, at Hawk’s Cay in Duck Key. Alex’s grandma used to be a member of this ritzy, family style resort and spa, and he talks about it frequently with great nostalgic fondness. We stopped here the last time we went to Key West, and so it has become a bit of a tradition. Though you’re not supposed to pop in for a drink, as they want members only, each time we have come and told them our story of how Alex spent childhood summer vacations there, they have allowed us to enter and enjoy the premises. We like the tiki bar at the pool that overlooks the lagoons. They have a great bar menu, perfect for a road trip snack and sip pit stop.
I really wanted to stop at the Sea Turtle hospital in Marathon, which is one of the closest keys to Key West, but sadly, it was past 6 PM when we got to it and they had closed. I heard great things about this hospital, and I love any excuse to interact with animals, especially turtles! So, next time!
We caught a fiery sunset as we drove into Key West. We had to first drop off our car rental at the Key West airport, which might be one of my favorite airports because it is so tiny, beachy, and laid back. There was one lady there to receive us who didn’t even look at the car and just needed our paperwork. Easy breezy. We got a cab from the airport to our inn and got to take in our first reacquaintance with the charm of Key West; a white and pastel grid of southern plantation style homes and funky beach cottages, bistro lit cafes, sunny and bright restaurants, nautical bars, and the sound of live music and the clinking of glasses… this is the soundscape and landscape of Key West, and what makes it an irresistible spring break dream. Our inn, Tropical Seascape Inn, was in a prime location, just off of Duval Street (quite literally) but yet on the quieter end of Duval and on a charming, quiet side street. Like many inns in Key West, the quarters are small, but we loved our inn’s little back patio equipped with a hot tub surrounded by palm trees, an ice machine, and an outdoor shower. We immediately went for a soak in the hot tub and relished the sound of palm leaves swaying in the gentle breeze.
We went for a super European dinner at 10 PM to a romantic spot called Nine One Five. The restaurant shares an old southern mansion with another restaurant upstairs, which might be equally as good, but we highly recommend Nine One Five. The kitchen was closing, but our server helped us out and got our orders in quickly. The food was exquisite and we sat out on the candlelit front patio, which meant we could enjoy some Duval Street people watching. Duval Street’s people watching is far more tame than South Beach, but still can be amusing.
After dinner we walked Duval to find a fun bar with live music. We stopped at a cowboy/saloon style bar, but it proved to be a bit too right wing for me… literally, they were playing Televangelist Joel Osteen on one of their TVs. We stuck around for a couple songs, before bailing and ending up at the famous Willie T’s. You’ve probably seen pictures of Willie T’s or been there if you’ve visited Key West. It’s the open air bar adorned in dollar bills on every nook and cranny of its walls and ceiling. In my opinion, they always have the best live music, and it is the epitome of Key West night life. We stayed until last call before heading back to our inn.
The following morning I decided to take a run, one of my favorite ways of getting a lay of my land in a new surrounding. Though I got caught in a brief sun storm, I oriented myself geographically and discovered a cute beach called Higgins Beach with a beach walkway running parallel to it.

Al and I enjoyed a perfect vacation breakfast at Banana Cafe. It’s a popular spot, so you can expect a wait, but it’s worth it. Fantastic ambiance and food. We wanted to have a half beach day but were undecided on which beach. The only downside to Key West, in our opinion, is there aren’t that many fantastic beaches. There are a couple, which I’ll explain in a moment, but to me, none of them are wow-worthy because they all have a great deal of sea weed that beaches itself on the shores and clumps in the shallow water. On our previous trip we went to Fort Zachary to explore the fort and go to the state park beach. The water is fantastic at Fort Zachary. It has the least amount of seaweed of all the beaches, however, there is a big caveat: no sand. It’s all rock and shell, even in the water, which makes laying out and entering the beautiful, tranquil waters, not so tranquil. It was scorching when we got to Fort Zachary, so we spent about 2 and a half hours there, mostly in the water, before deciding we needed some Pina Coladas and a stroll. We did a little shopping on Duval and, though we aren’t art officianados, something we like to do in new towns is browse the art galleries. Key West has many!

Something we did the last time we were in Key West was go on a sunset booze cruise, which is a complete must! We went through the same company as last time, Fury, and opted once again for the catamaran with a live band. This is such a delightful experience! The price is right, the crew is always engaging, the live music is wonderful, and in addition to unlimited booze, they provide platters of decent snacks and appetizers. Of note: a large charcuterie plate, which paired quite nicely with my Chardonnay. Sunsets in Key West, in my opinion, rival, if not supersede, California sunsets. The band aboard our Fury catamaran took requests, which got many passengers aboard, ages ranging from 8 to 75, up and dancing with their loved ones. It was such a sweet sight.


After our sunset serenade at sea, we walked from the marina to Blue Heaven, one of Key West’s most notable restaurants. We dined at Blue Heaven on our last trip and were completely smitten; the food, the ambiance, the live music, all make Blue Heaven a, fittingly, heavenly experience. Blue Heaven is a completely outdoor space sheltered by the intricate, intertwining, and infinite limbs of mossy draped Banyan trees. Rainbow lights project into the jungly canopy and an array of nautical, pirate themed paraphernalia adorn the live music hut, the circular bar in the center of it all, and the hostess stand. Though going barefoot is encouraged, there is nothing casual about the cuisine and service. The ambiance is unparalleled, but sadly, we weren’t as wowed by our meals on this visit as we had been a few years ago. Perhaps they got a new chef? Regardless, it’s a fantastic place worth visiting for dinner if you’ve never been.
After dinner we headed back to Willie T’s for another late night of ample cocktails and noteworthy live music. We were in complete awe of this one performer named Ike Kanakanui who was essentially a one man band. Just when we thought he couldn’t possibly play another instrument he would pull a different apparatus from a seemingly endless and magical pile of instruments ranging from a kazoo to a mini trumpet. We ended up staying until closing yet again, and talked to Ike as well, who proved to be just as interesting and free-spirited as one would imagine.
The next day Alex’s family was due to meet up with us as their cruise ship stopped in Key West. We all enjoyed a rooftop lunch at Schooners Wharf Bar and Grill at the marina. The food and drinks were good, service was meh, but the views were priceless. We then rented bikes and rode to the Southernmost Inn beach. Lounge chairs are astronomical at this beach so we splurged for only two, which didn’t bother us since most of us went straight into the water and didn’t come out for close to two hours. The water wasn’t that seaweedy, and this beach does have a smooth, sandy bottom, unlike the rocky basement of Fort Zachary. After bidding our family bon voyage, Al and I extended our bike rental for the next 24 hours and rode up and down Duval Street and side streets until just before sunset. Once sunset beckoned, we headed to the famous Sunset Pier for drinks and dinner. We lucked out and got one of the best sunset facing spots. I must say, we were pleasantly surprised by the food at Sunset Pier. It’s quite touristy, so the food would be expectantly garbage, but it was excellent. We watched our final Key West sunset send a shimmering flame through the horizon before the edge of the Atlantic slowly swallowed every last bit of orange radiance, blanketing the peninsula with twinkly dusk. We rode our bikes after dinner all over the town, up and down Duval, through the cemetery, and up and down side streets, before calling it a night.




Our flight didn’t depart until 2 PM the next day, so we got up early and, knowing the Key West airport is incredibly tiny and manageable, squeezed out every final minute we had in tropical paradise. We rode bikes to Pepe’s Cafe, the oldest dining establishment in Key West. We waited for a table in their outdoor patio, suitable for the likes of Jack Sparrow or Captain Ron, but then decided to eat at the weathered teak bar, where we feasted on a sweet and savory breakfast. After breakfast we rode our bikes to the beach walkway I had run to the previous day at Higgins Beach and rode until we got to Smathers Beach. We took a leisurely stroll along Smathers and discovered our error in spending our beach day at Fort Zachary. Next time we will absolutely be going to Smathers Beach for the day as it has a velvety stretch of sand, clear waters, water sports, and ample space for privacy and relaxation. We decided against Smathers as we heard the seaweed was inescapable and it caused an unbearable “low tide” aroma. This was not the case. Definitely get yourself to Smathers Beach for a beach day when in Key West.
After our beach discovery and stroll, it was time to pack up and head to the airport, which took us all of fifteen minutes total to get from our inn, to the airport, and through security to our “gate,” of which they don’t really even have, it’s just one big waiting area where they call your flight over the loud speaker.
All in all, our sunny Spring Break to Miami and Key West was a perfect balance of high-energy city life meets laid-back seaside escape. Every beat of live music, every drop of Pina Colada, every splash of salty sea water, and every fiery sunset defrosted us from our winter blues and healed our heavy hearts, heralding a return to lighter days and the dawning of a sweeter season ripe with hope, promise, and laughter.

