No Stress in Key West: Soaking Up the Sun on Ernest Hemingway's Erstwhile Island Home

(Photo: Jametlene Reskp)

Much like Luke Skywalker trying to fend off the Dark Side, or Batman beating back the urge to kill Joker — lest he escape and wreak havoc upon Gotham for the hundredth time — deciding to travel to what could only be described as a tourist trap is, for me, a gripping internal struggle. Niagara Falls, Cancún, Mackinac Island: I’ve been to a number of them in my day.

There’s nothing inherently wrong with that; it just means you’ll likely be hit with inflated prices at restaurants, inundated by gift shops selling an infinite number of frivolous knickknacks, and surrounded by hordes of the worst kind of people known to mankind: tourists. And if you now, in this moment, find yourself wondering, “But wait, wouldn’t I also be considered a tourist?”, then yes, you just might be. Meantime, the rest of us will concern ourselves with being travelers.

All right, calm down, I’m just kidding. I’m not that pretentious. All of this is really just to say that Key West, where my family and I decided to vacation for a week in early 2023, fits the bill as far as tourist traps are concerned. However, that didn’t stop us from having one hell of a good time — especially considering we escaped what proved to be one of the coldest weeks of the winter in the Midwest.

Key West wasn’t necessarily high on my travel bucket list, but it was on there (as is just about every other destination on planet Earth). Regardless, I figured it was better to visit sooner rather than later; that is, before the Florida Keys succumb in their entirety to the catastrophic effects of unchecked climate change and become the newest version of the Lost City of Atlantis.

So there we were, having come from Northern Michigan, Oklahoma, and Chicago, plopped down at the end of the line, the last spit of land at the very bottom of the continental United States. The weather? Sunny and 77 degrees Fahrenheit, or thereabouts, nearly every single day. The Airbnb rental? Centrally located, within walking distance (roughly 20 minutes or less) of just about anywhere you’d want to go. The possibilities to create core memories? Infinite.

On Duval Street, in the heart of downtown, there is typically more live music than you’d know what to do with

Come on Down to Duval with Me, Won’t You?

The first thing that comes to mind for many at the mention of Key West is Duval Street, which, as the heart of downtown, is a happenin’ place to be at all hours of the day and night. Lined with bars and restaurants, such as Sloppy Joe’s, Irish Kevin’s, and Lucy’s Retired Surfers Bar & Restaurant, this area is crawling with foot traffic all day long. In the evening, live music is the name of the game, with several spots playing host to local musicians, some of whom play for hours on end.

On the subject of music, there happened to be a festival taking place while we were in town. The five-day, country-infused Key Western Fest used Duval Street as its backdrop on opening night, with the kickoff event hosted on an outdoor stage assembled in the middle of the street. So, as Little Texas, Ricochet, and Kendall Marvel — the three acts performing that night — serenaded the crowd with their twangy tunes, we did as the Romans do: grabbed ourselves some adult beverages and swayed right along.

Over the first few days, there was one spot just off Duval on Greene Street, another main thoroughfare, that kept calling me back. This was Capt. Tony’s Saloon, which bills itself as the oldest bar on Key West, and the “original Sloppy Joe’s”.

Built in 1851 as an icehouse/morgue combo (now isn’t that something?), Capt. Tony’s has served as host to a number of big names over the years, including Truman Capote, Tennessee Williams, Jimmy Buffet, and the post-title-stealing son of a gun himself, Ernest Hemingway, who is said to have frequented the watering hole while living on the island in the 1930s.

The names of famous friends hang from the rafters at Capt. Tony’s Saloon just off Duval Street

From what I gathered, each of the bar’s famous visitors gets their name painted on a bar stool, which is then hung from the ceiling after they’ve passed from this life into the next. Sadly, one of the newer additions was that of college football coach Mike Leach, who died in December 2022 after suffering a heart attack. The stool bearing his name now hangs in between those reading “Papa Hemingway” and “John F. Kennedy” near a pair of pool tables in an area off to the right when you first walk in.

We visited Capt. Tony’s at least three times, maybe four, over the course of the first couple days on Key West, but after that it was time to try some other digs on for size. Two of the other bars we stopped at — Sloppy Joe’s and Irish Kevin’s — I’ve already mentioned, but there were also appearances at a pair of three-in-one combos.

The first was Rick’s Entertainment Complex, which is comprised of three separate venues. Rick’s Bar, a two-story watering hole with live music at street level and a live DJ upstairs, is what you might consider the heart of the complex. But then you also have Durty Harry’s, where you can catch house band The Durtbags once or twice a week, and the Red Garter Saloon, the self-described “premier gentleman’s club in the Florida Keys” (note: we skipped that one (this was a family vacay, after all)).

Just down the street, at the intersection of Duval and Caroline, another three-headed monster awaits. The Bull & Whistle Bar bills itself as the last of the old-time Duval Street open-air bars. At street level is The Bull, a larger space with a long bar, table seating, and décor that gives off Texas-y vibes. Upstairs is the Whistle Bar, where you’ll find pool tables, darts, and a balcony that wraps around the two street-facing sides of the building, where you can sip on your adult beverage of choice and judge all the peasants walking by down below.

Up on the rooftop is where things get truly wild, though. That’s because the Garden of Eden is a clothing-optional bar where people take that option seriously. While you can access The Bull and Whistle Bar for free, the Garden will cost you a small cover charge (I want to say it was $10, but don’t quote me on that). After you hand the man your cash money, you can head up the stairs and step into a whole new world. Keep your clothes on and take in the view, or jump into the fray; it’s totally up to you.

Key West’s South Beach can be found at the very southern end of Duval Street

Let’s Go to the Beach (-each), Let’s Go Get a Wave

Here’s something that might surprise you: there aren’t actually that many public beaches on Key West, and the ones that do exist aren’t all that big. A quick glance at a map of the island would tell you there are four main beaches. In no particular order, they are Smathers Beach, South Beach, Higgs Beach, and Simonton Beach.

The largest of the group is Smathers, which is very close to Key West International Airport on the south side of the island. Here you will come across all manner of activities to keep yourself occupied, including parasailing, windsurfing, and kayak and jet ski rentals. Much of this is offered through Sunset Watersports, which maintains one of several outposts at Smathers Beach. They also rent out beach chairs by the hour or the day (because, of course, you cannot expect such luxuries as a place to sit to be given away for free!).

Moving a little to the west, you’ll come across Higgs Beach, which was probably my favorite. About a 20-minute walk from our condo, there is a ton to do over this way. The beach — sporting a pair of volleyball courts, a playground, and an old military lookout surrounded by gardens — is the focal point, of course, but there are also nearby tennis and pickle ball courts, as well as a dog park. A key, key component of the experience, though, is the ability to order alcohols to-go at the window at Salute! On the Beach (where you can also grab a bite to eat).

Continuing westward, you’ll hit South Beach, where the main attraction (for those pesky tourists, at least) is the nearby buoy-shaped, concrete monument marking the Southernmost Point of the Continental U.S. In a sign of the times, there were still several stickers (or was it paint?) on the sidewalk leading up to the historical landmark urging everyone to stay six feet apart. The spacing and quantity of these safety reminders, which stretched a block or so, suggested we might have had to wait in a lengthy line to get those all-important family photos. Thankfully, however, we apparently stopped by at a good time.

South Beach itself features a quaint cut of sandy shoreline, a cute little pier that juts out a couple hundred feet into the water, and the Southernmost Beach Café — part of Southernmost Beach Resort (which you can read about yourself by following that link (did you think I was gonna do everything for you?)).

Those damn tourists, am I right?

Finally, you have the only beach we spent absolutely zero time at: Simonton Beach. Found on the northern side of Key West at the end of Simonton Street (shocking, I know), this appears to be the island’s smallest public beach. On either side of this tiny L-shaped stretch of sand sits Lagerheads Beach Bar & Watersports and the Blue Mojito Bar & Grill at the Hyatt. So you’ve got options there. Another great thing about Simonton is that it’s just a couple blocks from the heart of downtown, so you’re basically in the thick of things.

And, Finally, a Shoutout to Mother Nature

Look, friends and neighbors, I feel like this is dragging on a little, so allow me to wrap it up with one last item that deserves a mention. On Key West, there are a multitude of outfits that offer excursions out on the water, including Sebago Watersports, Fury Key West, and Ocean Vue Adventures. The day cruise we decided to do, however, was one organized by the lovely folks at Sunset Watersports. Their Sandbar & Kayak Eco Adventure is kind of the best of both worlds if you’re the type of person who likes a little alcohol with their nature.

We met the crew — Capt. Chuck, Spin, and Brynn — at the seaport on the end of William Street one fine morning during our weeklong stay before promptly climbing aboard “Miss Valyn”, the 54-foot catamaran that would carry us out into the blue waters of the Gulf of Mexico. The day trip was essentially a two-parter. After cruising a little ways out from shore, first up was kayaking through the mangrove islands.

Spin led the way and spit some fun facts about the scenery as our little kayak train choo choo-ed along. Mangroves, wouldn’t you know, can stand up to hurricane-force winds, and help stabilize Florida’s coastlines, reducing erosion and providing habitats for little Nemo’s and Dory’s. Additionally, and perhaps most importantly, they make for interesting visuals as you ride by in a kayak.

The second half of the Sandbar & Kayak Eco Adventure was where the adult beverages came in. Immediately after our rendezvous in the mangroves, lunch was served and the drinks began to flow. Captain Chuck steered us to a nearby sandbar once we were good and stuffed full of Cuban sandwiches, chicken tenders, and what-have-you, and then out came the floaties and the football and the frisbee. Now tell me: what could be better than day drinking on a sandbar in the ocean with the glorious Florida sunshine raining down upon your shoulders? Well, maybe world peace or something of that nature, but come on, we’ve got to be realistic here.

And, in the vein of keeping it real, I must now say this is the end of my spiel. If you’ve made it this far, congratulations. There are no prizes, but at least you can walk away knowing social media hasn’t totally fried your attention span just yet.

-LTH