I’ve gone Coastal on Ya

I’ve gone Coastal on Ya

After I relocated to Florida, I knew I wanted to visit the Keys. I figured that Memorial Day would be a perfect time to take a trip down to Key West. After asking around, I decided it would be another Third Wheel weekend with Heather and Lux. I had a blast at Epcot, so I knew this trip would be amazing too. We booked our flights, which were surprisingly more expensive than they should be. Being the Marriott devotee that I am, I found that The Saint hotel had the best location: directly off Duval Street. It turns out that the owner of the hotel also owns the hotel of the same name in New Orleans. And I love that hotel.


My flight into Jacksonville was delayed and delayed. I nearly missed my final leg. Luckily, I made it. Unfortunately, my bags did not. I finally got home at midnight. I had to leave for the airport at 4:30 AM. Awesome, who needs sleep, right? To my surprise, the baggage handler showed up promptly at 4AM, leaving me a little time to repack and still make my flight. I connected through Miami, so I at least got to hit the Centurion Club for some breakfast. I finally touched down on the island. Here is a pro-tip for you. Get a window seat for your incoming flight. It is truly beautiful flying in. We landed at the small airport, and I was ready for some fun in the sun.

This is the airport of Key West

The hotel was very nice. I was greeted by an incredibly attractive front desk staff member, and the bellhop whisked my bags away. This hotel has a very strong feeling of privacy and secrecy. I liked it.

The phrasing on the carpets at the hotel says it all.
This place felt like a private club

Day One

I was tired, but I knew I needed to rally. I grabbed one of the bikes from the hotel and headed out. I figured I could check out the brewery scene before Heather and Lux landed. I headed over to Bone Island Brewing. Turned out that this place isn’t a normal tap room, but more like a grocery store/sandwich shop/brewery… Whatever. I tried their beers. They were okay.

I love these postcard style murals

From there, I headed over to Waterfront Brewery. As the name implies, this location opens up directly to the water and marina. The views were amazing, but the beer was not. I liked some of their names. My next stop was Cork & Stogie. This place had my kind of vibe: some great taps, knowledgeable staff, good music. My next stop was the Southernmost Buoy to take my tourist picture.

Key West’s iconic buoy
Chilling at the southernmost point in the USA… #NBD

After this, I was wiped. I had sweat through everything, and needed some pool time. I ended meeting a pretty awesome crew in the pool, and it was happy hour from 4:17 to 7:14. So I partook of the 2-for-1 specials. The bar is really top notch. By the time happy hour ended, I needed a nap. So I closed my tab, and headed to the room. What I didn’t plan on was my energy crash. I hit the bed, and I was out like a light.

Day Two

Lux had to knock out some work, so I decided to check out the lighthouse and Hemingway’s house while I waited. If you visit Key West, I strongly recommend hiking up the Lighthouse stairs for the view. Here are some tips: bring hand wipes, bring a hand towel to wipe the sweat off, bring some water, and go early. It offers some amazing views of the island.

The beautiful church across Duval from my hotel
Looking up at the lighthouse
This whole island is very colourful and accepting

Then I wandered across the street to see the Ernest Hemingway house and his famous cats. This place is really cool, and you get a nice history lesson. The cats here really are polydactyl. It is quite interesting. They live the best life I could imagine: they are petted all day, they are fed, they relax.

I love this request outside the Hemingway House
This is my dream right here. Please note the extra toes
Apparently, this was the urinal from Hemingway’s favourite bar. When he learned they were closing, he told them he had pissed enough money away in there, so he took it.

Finally Heather made the sweaty hike from her hotel and we met up at Firefly for a little brunch. This food was amazing, We decided to start our Key Lime Crawl. From this point, we were going to try as many Key Lime pies as we could in a day.

This towering slice came from Blue Heaven

Lux was finally able to join us, but we were able to sneak in around 5 slices of pie first. And of course I had to be a tourist at the Margaritaville: Booze in the Blender

This frozen concoction that helps me unwind
Heather and Lux being tourists

We wandered around and listened to music, but we found the best music and food was at Smokin’ Tuna Saloon. It is a little off the beaten path, which is nice. The food was extra tasty, and the band was playing some fun tunes. We finished our night at Durty Harry’s. This place has a lot going on, but It was nice. Everyone was able to have something they liked. After Lux and Heather went to their hotel, I decided to hit up The Porch for a nightcap. I ended up running into friends from the hotel. So the night was young for me. From there, I hit up Senor Frogs and enjoyed the islands vibes.

Day Three

We wanted to hit a pool party, so we headed over to grab a quick brunch at Off the Hook. This ended up being our favourite restaurant,  so we actually booked it for dinner reservations. Their food is amazing, and to top it off, their waitstaff are all beautiful and wonderful people. What a deal! We grabbed a cab and headed out to Dante’s for our pool party. We were one of the first groups there (which I advise, strongly), so we picked our spots and grabbed a beer pong floaty. Lux and I proceeded to go on a 10-game streak, while Heather played wingwoman for me.

If I am going to be a third wheel, I might as well take cute pictures, right?
I need to pick one of these up for myself
he pool at Dante’s before the madness began

It turns out, if you come early to Dante’s and stay all day, you will probably end up missing your Sunset Cruise appointment. Oh well. The friends from the hotel pool showed up, and we had a grand ole time. We were able to rally and make our dinner RSVP. Thankfully, because the food was just as awesome for dinner. After dinner, I headed to get my tattoo.

Day Four

The time had come to head home, so I packed up and rolled out. They were able to have a fun day ou playing in the ocean since they had a later flight. Well, I wish I had brought my laptop, because they offered me a voucher, hotel stay, and rebooking the next day. But I couldn’t take it.


Yes, it is kinda cheesy. No, there isn’t a good beach. Yes, it is full of tourists. Bu I loved it. It felt like New Orleans on an Island. I would make a cool Bachelor Party destination. I recommend people without kids go check it out. I still want to go back for the sunset cruise, Dry Tortugas park, and the other keys.

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