Sumner Says

I recently traveled to Key West, Florida for a family member’s 21st birthday. It was my first time in the Florida Keys. Since I was going for a family event, I didn’t put as much effort into planning as I typically would for a long weekend trip. This was more of a go-with-the-flow kind of vacation.

Day 1

My girlfriend and I arrived in Key West mid-afternoon. We flew in to the only airport on the island. The first thing I noticed: the airport was very small. The second thing I noticed: chickens everywhere! Chickens were walking all over the sidewalks and in the streets.

We stayed at the Best Western Hibiscus Motel. My girlfriend was initially scared when I said it was a motel, but I promise it wasn’t scary at all. The price was reasonable and was within walking distance to Duval Street. The property also included a pool, which was a huge plus with the killer heat.

Our first stop was the Green Parrot bar. Google will tell you this is one of the most popular bars on the island. It was… fine. Pleasant atmosphere, but nothing to write home about. It did have free (but stale) popcorn.

The next stop was The Rum Bar. I can confidentially say I had the best drinks of the whole weekend here. I highly recommend the Mango Punch and the Painkiller. Even though the establishment was pretty small, we still managed to squeeze 7 people in at the bar.

The Rum Bar was close enough to walk back to our hotel for a quick break. This may be an unpopular opinion, but I’m a big fan of a afternoon break at the hotel. I need to get my second wind if I’m expected to make another appearance that evening. Plus, Key West is one of those places where you have to change outfits halfway through the day because you will sweat through your first outfit.

We ended the night at Kaya Island Eats. The service and food were great. I tried my first local delicacy, conch fritters, and they were a 10/10. The restaurant offered karaoke, but the clientele was really into sad country (a genre I wish I could un-hear). If you like thinking about your ex and questioning your life decisions, this is the karaoke bar for you.

Day 2

We kicked off the second day at the complimentary hotel breakfast. It was a decent spread – waffles, build-your-own bagel sandwich, fruit, and other common hotel breakfast items.

Some of our group decided to take the Conch Train Tour. The tour was amazing – honestly a highlight of the trip! We drove by many well-known tourist sites while the driver taught us the history of Key West (including the chicken lore). Taking this tour earlier in the trip was beneficial because it gave us ideas of where to visit the following day. The tour dropped us off next to a nice giftshop, where my partner and I purchased lots of rooster memorabilia.

Next stop was lunch at Ana’s Cafe Cubano. I split a Reuban and an Italian hoagie. I’d pick the Reuban over the Italian if I had to go again, but I likely wouldn’t return to this location. It was good for a quick bite though.

We hit The Rum Bar again (it was just so good the first time) and then traveled to the marina for Schooner Wharf Bar. While Schooner’s website boasts “best bar”, I’d say skip it. The bar sits right on the water and has a nice view, but the smell of someone gutting a fish left much to be desired.

After a brief hotel break, we were back at it again at the iconic Sloppy Joe’s. Now this bar was worth the hype. There was live music the entire time we were there. The opening act, Sloppy Seconds, was a duo who made me laugh and who I considered better than the main act. Food was available early in the evening. I had to try the Sloppy Fries, but honestly, the sauce was a bit too tomato-y for my liking. Later in the evening, tables were cleared to make a dance floor and we were able to dance our way into the night.

Day 3

Our last full day in Key West was the day for all the tourist attractions. We started our day at a cute little coffee shop, Keys Coffee Co. The food, coffee, and service were all superb. I had the avocado toast, which I’m always a sucker for whenever I see it on the menu.

We decided to visit several of the places we passed during the Conch Train tour, including the US 1 Mile Marker 0 sign, the Ernest Hemingway House, and the Southernmost Point Buoy.

The Ernest Hemingway House is worth seeing if you are:

1. A fan of the writer
2. A fan of cats

The writer’s house-turned-museum is home to 59 cats! We saw 35 / 59 on our self-guided tour of the house. Also, if you are a collector of Cat’s Meow Villages (I am), the gift shop sells portraits of the house and of Sloppy Joe’s Bar. I had to cop Sloppy Joe’s Bar, which is now sitting pretty over my office door.

I knew we couldn’t end our trip without trying authentic Key Lime Pie. Reddit revealed the best Key Lime Pie could be found at Blue Heaven. When we arrived at the restaurant, there was a 45 minute wait, but we were told we could wait at their bar across the street. When we walked over to the bar, we were pleasantly surprised to find they also sold the Key Lime Pie there! The pie was HUGE. While the flavor wasn’t my favorite, it’s still worth getting simply to cross off your bucket list.

Later that evening we grabbed dinner at Seaside Cafe at the Southernmost Mansion. Not only was there no wait at this restaurant, but we were sat right on the water. The drinks and the food were both amazing. If you like glorified chocolate milkshakes, I’d recommend ordering the Mudslide. If you like seafood, I’d highly recommend the half lobster / half street corn pizza.

General Horseplay, a Bill Murray inspired bar with speakeasy vibes, was the first bar of the night. The bar wasn’t busy or loud, so it was a good place to just sit and talk. This was a nice change of pace from the loud, boisterous bars we had been to previously.

Next, we made our way to Willie T’s. I would consider this bar another skip. It was loud, crowded, and I was served a different drink from what I ordered. We were only there a short period of time before we moved on.

The last and best bar of the trip: Bobby’s Monkey Bar. This cash-only bar was tucked away off the main street, but is well worth the trek. We had another chance at karaoke here and it was a much more upbeat karaoke experience this time around. People were actually singing the crowd pleasers (Wannabe by the Spice Girls, anyone?).

Day 4

Day 4 was the departure from hell. Don’t fly on a plane hungover. That’s all I have to say.

To summarize – Would I go again? Yes, but only for a 21st birthday celebration or a bachelorette trip. The party atmosphere is great for a celebration, but not for a romantic getaway. Overall, Key West was everything I thought it would be – partying, bars, and god-awful humidity.