Between the four of us in the Wiffullens crew, (Bobby and Christina Mullens, plus Will and Tiff), we like to go somewhere for one or two of our birthday’s each year. We did Barbados for Christina’s birthday in December, and local things for Tiff’s birthday in January, so for my birthday in March, we planned to do another group trip to Key West.
Planning For Four
We planned it all out accordingly, learning from our previous trips to Key West, and booked a room for four right on Duval street where we could walk or bike everywhere we wanted to go.
Unfortunately, a few days before the trip, our friends informed us they were no longer able to join us, leaving us scratching our heads on whether we should go with just the two of us, or cancel the trip all together. Well, the condo’s cancellation policy made it easy for us to decide whether or not to go, so we went just to have something to show for being $800 poorer.
The First Trip
We had been to Key West twice before, and still hadn’t determined how we felt about it. The first time was with Tiff’s family just two days after they helped us move all of our life’s belongings from Maryland down to our new home, Southwest Florida. So, it’s safe to say we were pretty overwhelmed and a little distracted during this first trip to Key West, but still had a great time together.
The keys were nice and all, but we left there talking about how over populated and a little “run down” Key West was compared to our little slice of paradise in Naples/Fort Myers.
The second time we visited, we had lived in Florida for more than a year already, and knew not to compare Key West to Naples. So, we embraced KW for what it was, a party beach town, known for drinking and spending too much…
And, that’s exactly what we did! Admittedly, it left a huge dent in our wallet, but also a lot of great memories with the Wiffullens crew. It was also our first time taking the Key West Express ferry from Fort Myers Beach over to Key West, which was about a 3-hour ride.
To be honest, we were scared at how much this third trip would end up costing with just the two of us. So we made a game plan: Bring alcohol and make our own drinks, stay on Duval so we don’t need a cab, and bring our bikes, so that once the car was parked, it didn’t move until we were ready to head home.
We also got a full briefing and spread sheet of “must do” items from fellow marina residents once they heard we were going to the keys. With this, we bought a bike rack for Elsa (Tiff’s car), loaded up the night before, and headed out early Friday morning!
On The Road Again
We stopped at Bahia Honda on Big Pine Key to have lunch, before heading on to Key West.
We Made It
Soon after making it, we hopped on the bikes, cruised past the Southernmost Point and hit the nearby “beach.” Side note, the beaches in KW are kind of a joke compared to ours in SWFL. They’re really just small patches of man-made sand piles, which doesn’t really classify as a beach if you ask me.
Anyways, when we were ready to leave, we realized we didn’t bring the key for the bike lock… So, we had to walk back to the house to get the key, before going back to the bikes.
Luckily, it was only 4 or 5 blocks away, so it was just a short 10-minute walk, and we were in Key West, how could we complain! Our place had the perfect location just off Duval Street.
Later in the evening we went to Mallory Square to watch the infamous street performers. Once I realized they made good tips, I volunteered to join in on the act. Not only did I not get any tips, the guy stole my wallet as apart of the act! Of course he gave it back, and the show went on, until sunset stole the attention of everyone in the square.
Being from SWFL, we weren’t all that amazed by the cloudy sunset, since we can literally walk across the street and see the big orange ball sink into the water every evening… spoiled much? I know.
It should be known that this trip wasn’t all pleasure. We were on a mission, and the mission was to say we’ve been there, done that, and got the T-shirt. In order to do that, we had to accept the Key West Cocktail Challenge. The challenge was to visit a series of bars, purchase their signature cocktail and get your “passport” stamped.
Some were tasty, like the Key Lime Pie Martini from Island Dogs, and others were pretty brutal, like the Oyster Shooter at Half Shell Raw Bar. After a delicious conch sandwich, we conched out pretty early because we had big plans for Saturday!
We booked the Yankee Freedom Ferry from Key West to the Dry Tortugas. So on Saturady we woke up before the sun, biked a mile and a half to the marina, and arrived to find the captain telling everyone to expect 6-8 foot seas, 30-40 mph wind gust, and pretty much guaranteed misery.
We knew we could handle some rough seas, after all we live on a boat… but we wanted our first time in the Dry Tortugas to be the complete experience, ie. enjoying the ride, the beautiful water color and weather, snorkeling, etc. Since this clearly wasn’t going to be the case, we opted for the full refund, and kind of winged the day from there.
We got over our botched plans rather quickly once we biked to our favorite breakfast spot in the world, Fire Fly, for their bomb-ass chicken and waffles and biscuits and gravy.
We did some exploring, some bar hopping, some shopping, and a lot of relaxing. We let our rebel souls loose as we snuck into an undisclosed location, and hung out at their seaside lounge for the duration of the day. We knew we had to preserve our energy because a night of raging was ahead of us.
The Duval Crawl
We were on our second day, and hadn’t even walked Duval street! So, by nightfall, we went to many of the spots on our “must do” list, and anywhere else there was entertainment. We had a great time eating a ginormous burger at Charlie Macs, people watching at various bars, singing along with the country band at Cowboy Bill’s, and joining the “shots train” at Senior Frogs.
Eventually we ran out of places to go as the town was shutting down by 2am. Well, there was one more place…. only problem was that there was half naked guys walking on top the bar with dollar bills sticking out of their whitey-tighties.
I remember the first time I walked by this place with Tiff’s brother, and was disgusted at the scene. This time however, I was more relaxed… maybe it’s the island lifestyle I’ve adopted since moving to Florida, but there was music and drinks, so what the hell, we don’t want to go home yet, right?
The Morning After
We woke up with a slight headache the next morning and decided we MUST try new breakfast place. Apparently everyone else had chosen the same place, so guess where we ended up?
Yup, back at FireFly. Hey, at least we tried different meals this time!
Cruising the streets after brunch, we heard a steel drum band at the Blue Macaw, so we popped in to listen a bit. Tiff secretly wants to learn the steel drums to compliment my ukulele, but have you ever checked the price of those things? Let’s just say it’ll be awhile before we buy one of those…
We’re Not Done Here
We rapped up our trip by picking up a conch horn, getting pictures at mile marker zero, the southernmost point, and all the touristy stuff people have to do every time they visit Key West.
By the end of our trip, we had completely changed our views of Key West… it was by far the most fun we’ve had there, and it was just the two of us, go figure!
On the ride home we laughed at our memories or lack-there-of. I mentioned, that I hadn’t seen a single Key Lime farm anywhere for the area being so big on Key Lime Pie. It was a 7 hour ride, so I did some digging, and to say the least, I now refer to KW’s hometown dessert as Key LIES pie.
To take it further, the “Conch Republic,” imports their conch from farms in the Bahamas!! We were shocked to discover that everything that makes Key West “KEY WEST” is IMPORTED, yikes!…
Whatever, Key West is still a fun place in our books. However, we’d rather explore new Keys and/or Caribbean islands before heading back to Key West again.
Okay, We’re Done…
Here are some highlights from our trip…
Watching cat videos playing on the TV at Island Dogs bar
Watching a bartender chase down a tab skipper
Stephanie and the free shot train
Random strip club discovery on the way to the country bar’s bathroom
Completing the cocktail challenge and getting our “free” t-shirts
Collecting drink coasters from every bar
FireFly, of course
Our secret seaside lounge discovery
The dancing pool guy and monkey coconut mug at Sunset Grill on Marathon Key
Places we visited:
Half Shell Raw Bar
Bourbon Street Pub
A&B Lobster House
*List to be continued whenever Key West Take Four happens…