When I was a kid, Key West was a tropical island paradise that could have very well been in a different country for how exotic it seemed to me.
I’d only been there two times on vacations with family before this February. Good times and good memories.
So, when my mom and stepdad (Dennis) offered Nick and I a paid two-day Key West excursion (all we had to do was pay for our food and entertainment), we had to jump on that!
Despite it being super busy at work, Nick and I took one day off and met my mom and Dennis in Ft Myers one very early Friday morning at the dock for the Key West Express.
Did I mention it was early? It was still dark.
Luckily our early arrival scored us some prime seats on the high speed catamaran, which turned out to be much swankier than I had expected. With cushioned seating around large tables for six, big screen TVs, a full bar and a lounge complete with small snack kitchen, this baby was stocked!
The seats were roomier than most planes or buses and some people really took advantage of them; like this guy…
(We thought he was dead for about an hour)
After the 3.5 hour ride directly to the port in Key West, we headed straight to our hotel, The Inn at Key West, which was located at the northeast end of the island. The hotel turned out to be one of the best parts of our trip – our own little tropical retreat of sorts.
After we had ditched our baggage in our rooms, we went down to the outdoor restaurant, Hammocks Cafe and almost everyone jumped right on the chance to order the first tropical drinks of the weekend.
I meanwhile started to go slightly delirious with hunger (early wake-ups always make me hungry)…
After we filled our previously rumbling bellies with some island-style fare (fish salad and salad for me), we decided to make use of the beautiful sunny day and take advantage of the lagoon style pool area.
Lucky for us, it had a pool bar. I mean, what is a trip to Key West without a Key Lime Martini to start things off?
By the time we showered and got ready to go out, it was just a couple hours before sunset. So of course, we went to the prime spot for Key West sunsets, Mallory Square.
The island has decent public transportation with their bus system, which we tried out for this trip. At just a couple bucks (less if you qualify for the senior discount – Dennis did and bragged about his discount the whole way to downtown), you save money, but be prepared for LOTS of stops if you are traveling from the opposite end of the island like we were.
Once we got to Mallory Square, we wandered through the back entrance and walked through all the street performers who had taken over big blocks of space for their acts. You’d think they organized some kind of schedule since there was always at least one act going, but they didn’t all compete for your attention at once.
There were a bunch of art vendors lining the water’s edge as well that you can peruse.
One thing I couldn’t help but notice was the chickens. EVERYWHERE. Baby chickens, momma hens and roosters where scuttling around the streets and sidewalks like I’m used to seeing squirrels. Turns out, they are the area’s version of pest control! Who knew?
Since it was mostly overcast that first night, we knew we weren’t going to see much of a sunset so we walked down the waterfront and into the shopping area of Mallory Square.
One of the most popular items being sold?
Why sponges of course!
Sponges used to be the big money maker for the area back before they were over-harvested. Then came the synthetic sponge and the sponge industry died down quite a bit. They still have plenty of the real thing on hand to buy though.
We opted for another purchase at this point though and followed Nick to his favorite Conch Fritter stand for our first sampling of these delicious fried delicacies.
They were incredible and after trying some from various points all over the island that weekend, I agree that this stand is the best. Their key lime mustard is out of this world!
One thing you almost have to expect to see in Key West is people in costume. We saw some folks dressed up in costumes who seemed to protesting… a variety of things. I’m still not quite sure.
Duval St. is the legendary avenue for all things drinking and eating in Key West and I can honestly say that by the end of the weekend, we covered pretty much every inch of that sucker.
The first night, however, we decided to take it easy with just a cursory amble to some of the legendary spots like Sloppy Joes (the original as well as the existing location).
But our stomachs got the best of us and we went off in search of a good seafood restaurant. After meandering the streets for almost an hour we found the Conch Republic Seafood Company on Greene St. and were thrilled to find that their food and drinks were all amazing!
I ordered a salad that turned out to be the size of my head and a a honey mojito that was possibly my favorite find of the weekend. Their bread though? It had coconut in it and possibly some pineapple. I’m not sure exactly, but I was addicted – it tasted like a less sweet pina colada!
We took a taxi back to the hotel that night, which aren’t that pricey if you have a group of four or more. You can spot them all over town thanks to their bright pink exteriors. They charge you per zone, so you don’t get different drivers charging you more.
Dennis and Nick tried the pool bar at our hotel when we got back, but my mom and I both crashed.
The next morning, I tried out the gym and then we all reconvened at Hammocks Cafe for a delicious breakfast. Our initial plan had been to go out on a snorkeling trip that morning, however, Mother Nature decided not to cooperate giving us a gusty day that caused our trip to be canceled.
Luckily we had our wonderful tropical retreat at the hotel! The pool lies in the center of the hotel so that the winds didn’t reach us as much. We spent most of the morning floating around the pool and enjoying the live pool entertainer (who even gave my mom a free hat at one point).
Once lunchtime rolled around we were back downtown on the waterfront enjoying a quick bite before we set out on our exploration of Duval St.
After another not-quite-sunset at Mallory Square, where we posed for our best group shot of the weekend, we walked from one end of Duval to the other, making stops along the way.
Important stops like The Flying Monkey Bar where you can create a frozen drink of your choice from an entire wall of pre-mixed concoctions. I think I had a Dizzy Monkey or something like that (chocolate and banana – it was yummy), but we all tried something.
We even stopped to book ourselves on a parasailing trip for the following day (and our final day in Key West) at one of the many Fury booths lining the street.
By the time we reached our goal destination, the La Concha Hotel Crowne Plaza Key West, it was dinnertime. We went straight to the roof deck for the undisputed “best views of the island” (so said every local we talked to).
It was a pretty spectacular view too.
But our growling stomachs beckoned us down to street-level before long and we dashed into the first restaurant we saw that looked appealing.
I’m pretty sure I went straight to sleep when we got back to the hotel that night too, but I was so exhausted I think I might have dozed off in the taxi.
Our last day’s plans were thwarted again on our last day, Sunday, by down pouring rain that began shortly after we woke up and continued the entire day. Everyone assured us that this weather was very abnormal for Key West at any time of the year, but it didn’t do us any good.
We kept our plans to go to the much talked about Blue Heaven for breakfast, but with the rain, we were put in one of their small indoor dining rooms (no chickens or live entertainment). Though the food was good, the atmosphere inside wasn’t anything special and we all agreed that the only spectacular thing about the food we ate and saw was that some folks were having foot-high slices of Key Lime Pie for breakfast (I so wish I had gotten a picture of that!).
It was like a monsoon when we left breakfast, so we were drenched by the time we reached the stand for the Conch Train Tours. We opted to jump on board and spend the rest of our time touring the island in the semi-covered trains. We didn’t exactly dry out, but we did learn and see a lot!
It turned out to be one of the best things we did.
Finally, it was time for us to depart so that we could wait in line for good seats on the returning Key West Express – it was Super Bowl Sunday and the Patriots were playing, so we HAD to have good seats near a TV.
The Pats may have lost the Super Bowl, but we were all really happy with our weekend adventure in Key West nonetheless.
Looking back at how much we accomplished, I have to admit it felt like we were there longer. There is so much to do, whether you want to go on tours or just lounge by the pool (the beaches aren’t anything to write home about), it’s hard not to have a good time in Key West.
It makes you understand where Jimmy Buffet got his inspiration for his upbeat tropical tunes.
It also makes me want to go back to Key West again in the near future, even if just for two days.
Have you ever been to Key West? What were your favorite things to do?