Our final approach into Key West International Airport was one of my most memorable so far. Looking out the window, a little smile suspended my cheeks in a dreamy state of cheerfulness as the turquoise waters of the Gulf of Mexico and the Atlantic Ocean met below us, guiding the way to the Conch Republic. We landed and took our phones off airplane mode and I let me family know we’d made it safely.
The airport grounds crew rolled up a ramp to the door of the plane, as though an impressive set piece in an extravagant production and we collected our bags, thanked the in-flight crew and bounced down the metal pathway, eager to get the day started after spending hours traveling. A warm breeze whipped through the air and the thunder of jet engines and nearby construction roared in our ears as we followed the fluid foot traffic from the plane, through the tiny terminal with car rental counters and an indoor bar aiming for island vibes, and to the ride-share pickup area. A hankering for cocktails by the water and a grumble in our bellies decided the itinerary for the afternoon, but first we wanted to drop our bags off at the hotel.
Mike summoned a Lyft and we were off. Our driver, a friendly man from Haiti, welcomed us to Key West and told us we would love it and, without prompt, assured us it was a safe place. “Nothing bad ever happened here,” he said, “You can walk around and just enjoy yourselves. You don’t have to worry.” We were not worried to begin with, but it was nice to hear his advice all the same and we were more than ready to walk around and enjoy ourselves.
Our driver dropped us off at our hotel, The Marker, and the staff at the front desk were friendly and accommodating when we asked to store our bags until our room was ready. Bag check tags safely stowed in my handbag, we made our way to Sunset Pier by the Ocean Key Resort & Spa to satiate my thirst for cocktails by the water. I ordered a Grapefruit Crush and Mike got a Florida Keys Brewing Co beer from the bar and we chose two colorful stools overlooking the water and the island of Sunset Key.
No view beats a water view, for me. Make that water turquoise and crystalline and I’m in love. Vacation had officially started and I grew pleasantly drowsy as the jetlag sat heavy upon on my eyelids, the fruity alcohol concoction going down easy, and the gentle sound of water lapped at the pier below and before us through the slats of the railing. We decided we were craving tacos and narrowed our preference down to Amigos Tortilla Bar on Greene Street as it was close and well reviewed and we were hungry.
We were seated immediately at an outdoor counter overlooking Greene Street, a prime people-watching station which I recommend as a top Key West activity. Across the street was Capt. Tony’s Saloon, a bar that boasted a claim of being the oldest bar in Florida, which we knew could in no way be true as we’d been to St. Augustine two years earlier. Still, as we waited for our food, we enjoyed watching the Capt. Tony’s patrons attempt to “feed” coins to the Atlantic goliath grouper suspended above the establishment’s sign, in hopes that good luck would follow them throughout their time on the island if their coin was successfully consumed.
Lunch was both delicious and refreshing. I opted for tacos, one pork and one shredded chicken, both on corn tortillas and an Islamorada Ale. We were still waiting on the text from our hotel informing us that our room was ready and I wanted to explore Duval Street. We paid the bill and set out to explore.
Duval street is packed with shops, restaurants, and people – hoards and hoards of people. The days we were there, we saw a large cruise ship docked in the port at Mallory Square which definitely contributed to the congestion of the Historic Seaport and Old Town neighborhoods of the little island. Though crowded, we’re not talking Times Square crowded, so we were hardly phased.
We perused the shops and architecture along Duval Street from the sidewalk and navigated south until we’d had enough of the kitchy offerings peeking out at us from shop windows, and changed course in search of the Custom House building, home to the Key West Museum of Art & History, which I had read sometimes displayed large sculpture pieces in front of the building. With no large sculpture on display to marvel at on our visit to the building, however, and receiving the text that our room was ready, we made our way back to The Marker via less busy streets, ingesting the local architecture with each colorful bungalow and guest house we passed along the way, feeling the heat of the afternoon Florida sunshine.
Our room at the Marker was spacious and bright with a king-sized bed, balcony overlooking a palm tree-ensconced parking lot, and a full bathroom equipped with both a shower stall and large soaking tub with key lime scented bath amenities. Mike took a nap and I finished editing a YouTube video and settled in, setting my suitcase on the luggage rack and sliding into my new, pink, satin, travel slippers which replaced my now-recycled, overworn, gray slides with the decorative bows.
Feeling refreshed after getting off of our feet for a couple of hours, we ventured to the outskirts of the Mallory Square Sunset Celebration in search of what all the travel blogs, vlogs, and Tripadvisor promised to be an unforgettable experience. The Sunset Celebration is held nightly and begins approximately two hours before sunset. The celebration is home to lively entertainment including street performers, souvenier and food vendors, live music, and hoards of tourists preferring to see the sunset through their phones instead of with their eyeballs.
It is said that the playwright, Tennessee Williams, began the Sunset Celebration, choosing to applaud the sunset from Mallory Square each evening, with a gin and tonic in hand (what a multi-tasker). Today’s celebration is a far cry from the magic of that image and the dreamer in me felt the experience was muddied by the circus-like spectacle. The crowd was applauding and began to disperse even before the sun reached the horizon, concealed by a cloud for the final moments of its descent, before colorful brushstrokes painted the sky.
We relocated to Sunset Pier next door for pre-dinner cocktails, settling in for the real magic as the crowds thinned and dusk approached. I’m a sucker for a cotton candy sky and this one did not disappoint.
We chose to have dinner at First Flight Island Restaurant & Brewery, a restaurant housed in, and adjacent to, the original PanAm ticket office. I am sorry to say it, but I do not have positive things to say about our dining experience there, beyond that the atmosphere of the outdoor patio was indeed very pleasant. Let’s just say we got to enjoy that atmosphere, and that atmosphere alone for a while, as we waited over thirty minutes for our drink order to be taken by someone who was allegedly not supposed to be our server.
Our drinks arrived about twenty minutes after that, delivered by the same “back-up” server who took down our food order which arrived over an hour later, delivered by our “back-up” server who also told us she had to put our dishes on the tray herself in the kitchen. Despite the lackluster service, we still had high hopes that the loftily priced food would be as delicious as the online reviews has promised. We were disappointed in that as well, unfortunately. If you are going to be a brewery and a restaurant and charge lofty prices, please aim to do at least one of those exceedingly well, or reduce your prices.
We decided to seek out adventure for the next day and signed up for a snorkel and sail tour with Island Jane Charters. We started our second day in Key West with brunch at Moondog Cafe. Walking up to Moondog and seeing the huge crowd outside was a little stressful as we were strapped for time, needing to get to our snorkeling rally point in a little less than two hours. I checked in with the hostess, a laid back, Audrey Hepburn admirer who assured me it would be no more than a fifteen minute wait and introduced me to the system of “putting your name down” at Moondog. She withdrew a box of laminated cards from the hostess stand and instructed me to, “Pick a card, any card.” I read the card I withdrew from the box, “Walt Disney,” the name instantly drawing to mind sunny visions of my friends Chelsea and Paige who each frequent Disney vacation properties.
“Are you really?” said the hostess with airy fascination.
“Why not?” I said with a shrug and a smile.
Sixteen minutes later “my name” was called and the hostess widened her eyes with a smile and said, “Shortest fifteen minutes of your life, am I right?”
We followed her inside, past the counter of freshly baked pastries on display and over to our little table beside a colorful floor to ceiling mural depicting Hemingway and the famous cats that now resided at his former property across the corner. Breakfast was delicious and any stress I felt melted away with the first sips of coffee and a few bites of my “Moondog Classic”. It was a relief to taste delicious food after my epic fail of dinner the night before.
We hurried back to The Marker to change for our snorkeling tour and got to the rally point in a less than direct way, but on time, only to be informed that snorkeling the reef was not possible that day due to the recent windy weather making the water too murky to see anything. The sail was still on offer though, and boasted unlimited drinks. We’d get a partial refund if we chose to go on the sail or a full refund if we preferred not to. We decided that already being there and in search of an adventure, that we’d join for the sail and it turned out to be a fun and informative way to pass a couple of hours. Being out on the water alone was worth the price.
One thing first time visitors should be mindful of when visiting Key West is that there are not sandy beaches where you can wade into the water barefoot and bask in the gentle tide. Beaches in Key West, other than Smathers Beach, outside the historic, walkable downtown, are manmade and rocky (and crowded!). It is better to go in search of the plethora of watersports, cruises, and activities offered to satisfy your splashy goals and search for those breathtaking views.
We sat poolside at the Marker for a while after our sail, enjoying live music up until the point where an attention-hungry, over-tanned, grown man decided it would be fun for everyone to experience the interactive journey of him canon-balling into the pool. Next was our old haunt, Sunset Pier, then dinner at what I was hoping would be an excellent Cuban restaurant. (First Flight really pummeled my restaurant confidence, can you tell?) We changed for dinner and walked to El Siboney in the Old Town neighborhood. The place was crowded with tourists when we sat down so I had high hopes it would live up to the hype, and live up to the hype it did.
I ordered the ropa vieja (shredded beef with onions, peppers, tomato, and spices with a side of white rice and black beans) and Mike got the lechon (slow roasted pork marinated in sour orange mojo with onions and a side of white rice and black beans). We both decided it might be the best ropa vieja we have ever tasted and we have tasted some excellent ropa vieja, let me tell you.
We walked back to The Marker, our bellies full, breathing in the humid evening and dodging palm fronds as we passed the colorful bungalows that hugged the sidewalk, warning us to Beware of Flamingos and informing us that Life’s a Beach. We made our way along the streets, many with names of members of British royalty and returned to the Marker, satisfied with our adventures for the day.
We drifted off to sleep, sheltered by the palm trees, enveloped in the welcoming conch spirit, our rental car and Florida Keys road trip lying in wait. We went to Moondog again for one last meal before heading to the airport to collect our rental car and drove east with the thought that one more day in paradise would have been just right.
cozy does it 