How I spent 3 days in Key West

Being born and raised in Florida, traveling to Key West is like the pilgrimage to Mecca; you have to go at least once in your life. I can’t believe it’s taken me 31 years to make it there, and of all the times to go, I decided to go in the middle of this never-ending pandemic. Florida is officially in Phase III of reopening, which means everything is full capacity, but you have to wear a mask. I can comply with that. I feel naked without my mask, anyway. 

Key West – Day 1

Monday morning, I flew down to Key West on Silver Airlines. Since I work in aviation, I was super excited to fly on the new ATRs. As boarding began, the gate attendant announced he was “boarding all groups, all rows,” and jokingly herded all 15 of us to, “get in line and get out of here.” Once on the plane, the flight attendant said we could sit anywhere we like and to, “please keep your mask on and enjoy the flight.” Yes! With a window seat and a row to myself, this vacation was starting on the right foot.

The weather couldn’t have been better, either. We must have had a tailwind because we arrived half an hour early. Not to worry, this gave me time to shamelessly take selfies in front of the terminal and watch the local roosters run after arriving passengers in hopes they could shake them down for food. 

Tiny island Beach in key west - Things to do in key west.

Where We Stayed – Ocean Key Resort & Spa

I arrived at the Ocean Key Resort & Spa just before noon, meeting up with Aaron and two of his best friends. They drove down on Saturday and had been in vacation mode for a few days. Wasting no time, we changed into our swimsuits, made a cocktail, and headed to the pool, that happened to be an entire 3 feet from our balcony.

Have I already said the weather was perfect?!?! Because it couldn’t have been more beautiful outside. Florida has a way of teasing us with comfortable temperatures and low humidity every once in a while; the kind of weather you imagine when watching one of the Corona ads of a couple on white sand beaches, hearing the waves lap peacefully against the shore. That weather. The four of us set up camp in a cabana. Aaron was diligently “working remotely” poolside, while the rest of us floated around the pool for most of the afternoon. I alternated between sitting in the shade, jumping in the pool, and then eventually joining Aaron is the cabana for a much-needed nap. 

Things to do in Key West - Stay right on the water

Where To Eat

Our hotel was steps away from all the famous landmarks and bars. Our first stop of the evening was to a small stand on Duval for some very hot and delicious conch fritters. They were just what we needed after spending the afternoon lounging around the pool with little more than daiquiris in our stomachs. Not to let our buzz fade too much, we stopped in Capt. Tony’s Saloon (the original Sloppy Joe’s in the 1930s). If you’re not privy to the goings-on in the life of American writer Ernest Hemingway, you will quickly see Key West is an homage to his life and legacy. Capt. Tony’s proudly displays a sign on the outside of the saloon boasting the patronage of Hemingway.

I imagine the bar looked very different when Hemingway frequented the bar in the 1930s than it does today. Today’s Capt. Tony’s is decorated with women’s bras and dollar bills lining the rafters. Every inch from the wall to ceiling is covered. It’s a sight to see. Who knows, maybe Earnest himself started the bra trend; he did have quite the way with the ladies. Not to miss out on the fun, we of course signed and added our dollar to the bar’s wall.

We finished our drinks at Capt. Tony’s and set off for dinner, eventually finding ourselves at Jack Flat’s. This was a covenant stop for dinner because they had food (which I desperately needed), and the final game for the Stanley Cup just started. We ordered more drinks, the food was plentiful, and the Tampa Bay Lightning won the Stanley Cup! I’m not into sports (unless it’s the Olympics), but a win for a home town team is always cause to celebrate. After returning to the hotel, I went to bed early while the boys headed off to the pool for a late-night swim. The next day was going to be full of activities, and I simply couldn’t hang anymore. 


Key West – Day 2

Tuesday, I woke up feeling recharged. Eight hours of sleep on the most comfortable mattress and the room temperature set to below freezing helped start the day off right. We all shuffled around, getting ready while deciding where to eat breakfast. Aaron was adamant about finding a breakfast spot with the best Bloody Mary. Wouldn’t you know it, The Breakfast Club, too, proudly proclaims on the home page of their website “Best Bloody Mary in Key West.” Sold! 

At breakfast, we each order a different Bloody Mary. Then, coffee orders, a Nutella French toast appetizer, and eggs benedict. Everything was delicious! My Bloody Mary was the “Fire Mary” which had the perfect amount of spice and acidity. While we ate breakfast, we began to formulate our plans for the day. Since this was my first time in Key West, the guys planned the day to go to all the touristy spots with me. We finished breakfast stuffed (and with leftovers, which I would think myself of later) but ready for the day. 

Bloody Mary's - Things to do in Key West Florida.

Tuesday was quite a bit warmer than Monday. So, instead of walking around the island, we decided to rent bicycles; this was the best idea! I highly recommend biking to all the must-see destinations. It saved us so much time, and we didn’t melt in the Florida sun. After picking up the bikes, we set off for the Hemingway house. I’m not the biggest Hemingway fan. I read “The Sun Also Rises” in school and remember learning about his life (mostly his womanizing and love for rum). What I was most excited about were the cats! They are famous for being polydactyl, meaning they have six adorable toes.

They did not disappoint. The property has over 50 cats in total, all related to the first polydactyl cat gifted to Hemingway by a ship captain. While we waited for the next tour to begin, we roamed around the property, taking pictures of the cats and counting their little toes. The tour started inside the home, which was air-conditioned to my surprise (Thank goodness!). Each room represented a different time in Hemingway’s life, from his time as a war correspondent through the nine years he lived in Key West. My favorite part (besides the cats) was learning about his dedication to writing and seeing his office, untouched, exactly how he left it. 

The Hemingway House
The Hemingway Bathroom
A Hemingway Cat

We said goodbye to the cats and biked down the street to the Southernmost Point Buoy. A popular tourist spot marking 90 miles from Cuba and being the most southern point in the U.S. The line for pictures wasn’t long. We waited under five minutes, got our photos, and hopped back on the bikes. Weaving up and down the streets, we stopped to take pictures and read historical markers, making sure to hit all the highlights. Sufficiently tired and hot from biking the island, we headed back to the hotel to change for our snorkeling sunset cruise. 

I was most excited to do a water activity because Aaron and I had matching swimsuits. It has been a long journey to get Aaron to agree to match outfits, but he is now totally on board. We bought these swimsuits in January by mistake. We walked into a Cubbies store to look around and came out with three swim trunks for him and a swimsuit for me. Snorkeling was our first opportunity to wear the swimsuits together, and I was so excited! 

The snorkeling activity we booked was Rum & Reggae Snorkel Sunset Combo with Fury. We loaded up on the catamaran and sailed for 45 minutes to the snorkeling location. We weren’t able to go to the coral reef on this day due to high seas, but the alternate site was just as plentiful with sea creatures. One of the crew members was able to find a nurse shark and a massive grouper. The best part was the stingrays. I’ve seen schools of stingrays swimming together in the ocean from a pier, and I’ve seen them in aquariums. It was a whole different experience seeing massive stingrays buried in the sand with just their eyes poking out while swimming over them.

The water was perfectly warm, and the wind was blowing just enough to keep you cool. After snorkeling around for an hour, it was time to get back on the boat; as promised, the crew members opened the bar, and reggae music echoed in all directions around the ship. The four of us spent our time taking photos and refilling our cups with rum-punch or champagne (or in Aaron’s case, champagne mixed with rum-punch). The sunset was on cue with us entering back into the marina. The last moments on the boat were spent watching the sun slip below the horizon and discussing whether or not Rose could have let Jack on the door after the Titanic sunk. 

Sunset Cruise after snorkeling - Key West Florida
Sunset after snorkeling. The cloud in the distance was said to look like the Titanic. Sparking the debate; did Rose have room on that door?

We may have had too much to drink on the boat because we scattered in different directions once we were off. I ran to the hotel to use the bathroom, and Aaron bought a painting (it’s stunning, so I can’t blame him) from a local artist Isaac Valdes at Key West Sunsets. Not only are the canvas photos so vivid you feel like you are on the beach, but Isaac’s wife, Danay, creates unique customs frames for the art work from recycle lobster trap wood collected from fishermen in Key West. The art work and the use of recycled material will make for a beautiful conversation piece in Aaron’s home for year’s to come. 


Eventually we regrouped at the hotel to shower and change. We spent the night on Duval Street, hopping from bar to bar. We ran into some a couple were on the snorkeling cruise with us. They complemented Aaron and me on our matching swimsuits. We decided to hang out, grab a pizza, and listen to some live music. As we were getting ready to head back to the hotel, the smallest but mightiest rain cloud began dumping buckets of rain. While we all wanted to wait it out, as grown adults do, Aaron insisted on playing in the rain. Being it was late at night on an empty street, we took the opportunity to take pictures and jump over the careening rivers that seemingly appeared out of nowhere. 

Sloppy Joes in Key West Florida - Things to do in Key West

Key West – Day 3

Wednesday, we drove back to Tampa, but not before stopping by Sloppy Joe’s, where the guys had made friends with the bartender and were hoping to see him before we left. Unfortunately, he wasn’t there. However, we did take the opportunity to order Sloppy Joe’s (hence the name) before we started our drive back. It’s no wonder they named the bar after them; this was the best sloppy joe I’ve ever had! The bartender suggested adding shredded cheese, and she wasn’t wrong. A little food was all I needed to bring me back to life after yesterday’s adventures. 

Sloppy Joe's in Key West Florida

We couldn’t leave Key West without Key Lime Pie. Many of the places for Key Lime Pie were closed for the season, but luckily, we were able to stop by Kermit’s Key West Key Lime Shoppe to fill our cooler with six pies for friends and family to enjoy. 

Things to do in Key West - eat key lime pie.

A trip to Key West was the vacation we all needed. If you’re ready to travel, I would highly suggest putting a Key West adventure on the list. The cruise ships aren’t currently making port calls, which has drastically reduced the number of tourists visiting the island, so if crowds are not your thing, now’s the time to go! Also, if you enjoy supporting “local” business, they will appreciate your patronage. Even though this has been a trying time, every person we had the pleasure of interacting with was living their best life, making the most of it. They are the ones that keep this southern island paradise alive.

12 thoughts on “How I spent 3 days in Key West

  1. I love Key West. I can picture in my mind the roosters chasing passengers around at the airport looking for a free lunch, We’ve been to Hemingway’s house. The six-toed cats are awesome. They own the place. I’m glad you had such a great vacation.

  2. I visited Key West with a friend last year over Labor Day weekend. It was such fun. I can’t wait to go back there. We were lucky that the three days we were there, no cruise ships dumped passengers off and it wasn’t all that crowded. We used the hop-on, hop-off bus to get around. I’d be worried about drinking and biking.

  3. A few years ago, we met some friends from Spain in Miami where he had some business. After a few days we got bored with Miami and decided, on a whim, to drive to Key West. We loved the place and had a great time. We would love to go back, but, being from Seattle, we are about as far from Key West as you can get, and there are so many places to see. Thanks for the revisit.

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