Key West, Fl – What’s all the Hype?

As with any place, the experiences you have are at least somewhat dependent upon your expectations. It had been over twenty years since Hakam was in Key West, a place he often referred to as Paradise, so his only expectation was that it hadn’t changed since he left. Twenty years is a long time for things not to change, however. I had never been there, and although very excited about visiting, I didn’t really expect it to be “Paradise.” I wouldn’t even know what paradise looks like, as I’m sure it comes in many forms. I did want to experience something new and different, however, and maybe come to understand the obsession people seem to have with the tiny island. We were only going to be there a week, so I wasn’t sure that would be enough time to figure out what all the hype is about.

Mallory Square – One of our first stops was Mallory Square. A famous slab of concrete seemingly reserved for sunset watchers and street entertainers. This is the place where people from all over the world gather to eat and drink, socialize, sometimes dance, watch with envy as yachts float by, and allow themselves to be awed by entertainers working for tips. And then, like clockwork, everyone stops whatever they’re doing and turns their attention to the sun. The whole crowd is in unison as everyone faces the same direction to bear witness to what is known as the finest sunsets on earth. At least that’s what I heard. Unfortunately for us, that wasn’t the case. It rained a lot the week Hakam and I were in Key West, so the sunsets we witnessed at Mallory Square were a little less than impressive. It was clear during the day, but the clouds just wouldn’t cooperate at night. Luckily, we were able to catch a beautiful sunset right outside our tiny home at our campsite. We had an oceanfront seat to the spectacular show, and it felt like we were the only people in the audience. It was personal, and much better than sharing it with hundreds of people. We were so grateful for that, because visiting Key West without being able to sit back and take in a beautiful sunset would be criminal! As for Mallory Square…. with or without a spectacular sunset to gaze at, it shouldn’t be passed up. It’s an interesting social event, and depending on the night, some of the entertainers actually have talent. The others are just weirdos. At the very least, it’s a great place to people-watch. You won’t be disappointed!

Duval Street – Because I don’t think it’s possible to visit Key West and not explore the infamous Duval Street, we found our place amongst the crowd of tourists and herded along the never ending row of t-shirt and gift shops and restaurants and bars. Anything from post cards and conch shells to art galleries and fine dining can be found on this street or any of the adjacent ones. The streets are congested with vehicles, trolleys, mopeds and scooters, rental bicycles, and bicycle taxi’s. Crossing some of these streets takes skill! And if your exploring the area with your four-legged traveling companion like we were, many of the stores place a bowl of water, or even treats, on the sidewalk for the thirsty pups.

At night, Duval Street turns into another animal. If you came to key West to “party”, or just consume alcohol until you’re comatose, Duval Street stands ready to accommodate. There are too many bars to list, but the infamous Sloppy Joe’s is one of them. As you might expect, it’s loud. One bar seemingly trying to drown out the neighboring bar’s music or live band with its own. It’s still congested with all the same modes of transportation, but the traffic is moving at a much slower pace. I assume the drivers are either cruising the strip taking in the sights, or busy concentrating on keeping their vehicle between the lines. There are tons of people walking the street, undoubtedly moving from one trough to the next. There are drag-queen shows, clothing optional clubs, and strip joints. Whatever you’re looking for, Duval Street has it. And then periodically, situated amongst all the chaos, loud music, and staggering drunks, an upscale restaurant, with its formal- attired patrons dining on an outside patio, appears from nowhere. And contrary to assumption, everyone seems to co-exist peacefully. It’s so odd it makes sense. Duval Street isn’t really our scene, day or night, but we weren’t about to visit Key West without checking it out. I’m glad we did.

Dining – Food is pretty much the first thing on our minds whenever we visit a new place. I’d say we like to immerse ourselves in the culture through food, or something sophisticated like that, but the truth is, we just like to eat and going somewhere new gives us an excuse. We certainly can’t afford to dine out daily, especially at Key West prices, but we budgeted for a couple lunches and dinners during our stay to satisfy our love for it.

Key West has no shortage of restaurants and a ton of variety as well. If you think it’s all seafood, you’re wrong. There are of course countless seafood restaurants, but there’s also Cuban, Mexican, Italian and Thai cuisine. There are also breakfast, lunch, dessert and coffee cafe’s everywhere. The restaurants available are overwhelming, but even with all those choices, Hakam seemed to be obsessed with just one. Before we even arrived at Key West he was talking about a restaurant called Bo’s Fish Wagon. He referred to it as a “shack” or “hole in the wall” type of place, but said it had the best fried grouper sandwich and that the restaurant was well-known for it. He went on and on about this place and how he used to eat there all the time. He couldn’t wait to get there, so this was our first budgeted lunch. He finally got to consume the famous grouper sandwich he’d been missing for over twenty years. It was definitely “something,” both the food and the experience, and we’ll tell you all about it in our restaurant reviews post!

During our stay in Key West we also dined at Schooner Wharf, The Stoned Crab, Pepe’s Cafe, 5 Brothers Grocery and Sandwich Shop, Blue Heaven (take out only), and Kermit’s Key Lime Shoppe. There were others we had pegged as our first choice, but they weren’t dog-friendly, so we moved on. A couple of the restaurants we dined at were excellent, while the rest ranged anywhere from very good to shockingly poor. A full review of all these restaurants, which will include information about the food, service, cost, and atmosphere, will also be available in our restaurant review post. They won’t all be good, in fact at least one of them will be border line brutal, but they will be honest.

Key West is very expensive, and their restaurants are no exception! You might think that because a restaurant is expensive their food is going to be wonderful, but that can be so far from the truth sometimes. The cheapest meal we had was by far the best. If you’re planning a trip to Key West any time soon, be sure to check out the reviews. It could save you a lot of money!

Off The Beaten Path – Having the benefit of a former Key West resident as my personal tour guide, we didn’t stick around the commercialized areas too long. Sure, we did the “touristy” thing, briefly, because it would almost be negligible not to hit attractions like Mallory Square and Duval Street, but we quickly headed off the beaten path to see what Key West is really about.

Just more than a few blocks from all the chaos, we found ourselves walking the tree-lined streets of neighborhoods lived in by the locals. It was quiet and calm and had a completely different vibe than where we just came from. We were no longer feeling claustrophobic since we freed ourselves from the herd, but then we started wondering how we were the only people with this idea. Why weren’t there more people like us over here? We weren’t sure what the punishment was for not following protocol, but we were ok with not knowing as we strolled along the sidewalks taking in the perfect combination of beautiful older homes and smaller quaint cottages. Although all of them priced at the typical Key West fortune, and beyond reach for “normal” people, none of them were intimidating or made us feel like we didn’t belong. The houses, like their owners, presented as casual and welcoming with a whole bunch of character and charm, and plenty of stories to tell, I’m sure.

Mingled throughout the neighborhoods are local businesses lacking newer façade, flashing lights, and neon signs…. thank God!  And amongst all those is a small unassuming market, that doubles as a restaurant, called 5 Brothers. Hakam remembered it as a local’s favorite from when he was stationed there. Eager to see if it “stood the test of time,” but more eager to eat, we entered the little business and placed our order. Although there’s seating available inside, we chose to eat our Cuban sandwiches, and later drink our Cuban coffees, outside on the benches under the awnings.

Here we were greeted by locals gathered to eat or just enjoy the company of those who were. All, however, more than happy to give their history and listen to ours. We told our story about how we traded in our old life for a new one, and they told theirs. We learned about the Key West neighborhoods we admired so much, the sky-high real estate prices even wealthy people can’t afford anymore, and how the hordes of tourists can be overwhelming for the locals. We understood this having just left Charleston, SC, a city also known for attracting them. We even met a long-time resident of Key West who frequently visited Charleston and was familiar with all the same places, and even the roads, we were. Small world!

We watched people come and go from this quaint little business serving up delicious food, but they always stopped to chat it up with those sitting outside. Although I was engaged in conversation at the time a casually-dressed gentleman stopped by, I was later informed he was the former Mayor of Key West. Nothing about him would have suggested it, which is a good thing. We saw marked and unmarked police cars pull up and leave after brown-bagging their order, so they could eat on the road, but none of them forgot to wish us all a good day. The “everyone knows everyone” feeling we got the moment we stepped off the beaten path was without a doubt confirmed…. and we loved it. Who would have thought that our delicious lunch at a very reasonable price came with a side of new friends!

And no worries……our pup Richey wasn’t left out or ignored. Key West is very dog-friendly, and the locals are even more so. Richey was adored and showered with pets and hugs. He was even lucky enough, but probably more like cute enough, to be allowed a visit to the 5 Brothers “secret door” where one of his favorite things in the whole world awaited him. I’m sure the “door” is a highly-coveted island secret, so I’m not comfortable revealing information about it without permission. But please, if you visit Key West with your furry four-legged friend, do not deprive him or her of this experience. If you’re not already, this stop will make you his or her hero!

Needless to say, since we were in Key West for a week, there was plenty of time to return to our now favorite spot to eat at and additional strolls through the island neighborhoods we’d come to love so much. I’m so glad we decided to break away from the herd, because I think we would have missed out on “Key West” if we hadn’t.  As for expectations…. maybe the best expectations to have is to have none at all, and to be open to whatever and whomever comes your way. Just wear comfortable clothes, relax, go for a stroll, have lunch with strangers, and make a new friend. It’s worth the trip. And yes, I can see what all the hype is about.

Thanks for reading! Please don’t forget to share this post on your social media and subscribe to our blog before leaving the site. Sharing and subscribing is a way to support our content, which makes it relevant and helps to get it seen by more people. We love the work we do, but we can’t do it without you! Until next time…