For years, I’ve considered myself a professional Man of Leisure. I have nothing against working hard, but I like to pick and choose when and where to exert my efforts (such as this Guide to fun things to do in Key West). The old adage “work smarter, not harder” might as well be my personal mantra. I subscribed to it through high school, college, and every job I’ve had in my entire life.
Of course, now I live in a van, so maybe I should have worked harder at something. But let’s not quibble.
When Tiffany and I decided to sell our house and go on this adventure, Key West was a non-negotiable destination. For a man of leisure, it’s quite possibly the best place to visit in the country. Sure, there’s the fishing. And the restaurants. Not to mention the laid-back lifestyle. But mainly, I wanted to take Tiffany to Key West because, despite being born and raised in Florida, she’d never visited the Keys.
Additionally, after being together for nearly 10 years, I decided that if Tiff didn’t like Key West, we should probably call it quits. My only hope was to do my best to turn Tiffany into the woman of leisure she was always meant to be.
Therefore, I presented to her (and now you) this, my magnum opus: A Leisurely Guide to Key West. Follow along closely. These ratings may save your relationship. Or your life.
Try as Many Key Lime Pies as You Possibly Can
Look, just about every restaurant in the Keys will tout its Key lime pie. My suggestion: try them all. Some have meringue, like the pies at Blue Heaven. Others have lime slices and whipped cream. The best ones (at least in my opinion) have a graham cracker crust. But almost all of them are different.
Heck, Kermit’s even features chocolate-dipped Key lime pie slices on a stick. Those were so tasty that Tiffany and I went there twice.
We’re not gluttons. You’re a glutton.
The bottom line here is that you can’t have too much of a good thing. Everyone has different tastes, so why not work through the process of elimination and find the Key lime pie for you. And if you don’t like Key lime pie, then I’m not sure I can help. That’s a you problem.
Leisure scale: 8/10
Eating pies after every meal might be a requirement of the leisurely lifestyle.
Spend a Day at Smathers Beach
For most of my adult life, I abhorred the beach. I don’t like getting sandy. Or wet. And I hate the feeling of having suntan lotion all over my skin. (Side note: Tiffany makes fun of me for calling it suntan lotion. I guess it’s sunscreen? Sunblock? Sunarmor? I don’t know.) Basically, I used to turn into a huge baby anytime I ended up at the beach.
Things changed in the Keys. For the first time in my life, I actually suggested relaxing by the beach for a day. We chose Smathers Beach, which turned out to be a great choice. The crowds weren’t too bad, the chair and umbrella rentals were quite reasonable, and the water was a pleasing temperature. I even took my shirt off to try and get some sun(!).
This would be my first step to becoming what I call a Super Tan Man. These are the guys you see at the beach with the sun-drenched, leathery skin who never wear shirts. They look awesome in the way cigarettes make everyone look cool. My ultimate goal now is to become a Super Tan Man of Leisure. But, I digress.
The day we went to Smathers also happened to coincide with the Blue Angels performing at the nearby NAS Key West Southernmost Air Spectacular. So every now and then, Blue Angel F/A-18s would fly directly over us. Not a bad day at the beach, if I do say so myself.
Other rentals are available here, as well. Kayaks, stand-up paddle boards, and other recreational watercraft can be rented for the day. Since I’m not the greatest kayaker, and I refuse to even try a SUP out of principle, relaxing in the sun turned out to be just what I needed. Do yourself a favor and spend some leisure time at Smathers. You won’t regret it.
Leisure scale: 9/10
Some people will smoke cigarettes around you, and it does get very hot. But still, quite leisurely. It’s literally a day at the beach.
Visit Mallory Square for the Sunset Celebration
Okay, so this is pretty touristy. And it gets really crowded. Those are typically two things that lead me in the opposite direction; however, the Sunset Celebration is something you simply must do if you go to Key West. Artists, musicians, and street performers turn out in droves, creating an interesting spectacle with a magnificent sunset as a backdrop. Did I mention the crowds, though?
The night we checked this out, two dudes performed acrobatics on a ladder, a spaced-out old guy tried to walk a tightrope while juggling, and another guy fit his entire body through a tennis racquet while perched on a balancing board on top of a table. You know, just regular stuff. But this happens every night. You really need to check it out at least once.
Be warned, however, that every single person there will be trying to take a photo of the sunset. Unless you get there early and stake out a spot along the water, you’ll end up frustrated and cursing. Or maybe that’s just me. But that leads me to the next item on our list.
Leisure scale: 5/10
There is too much going on for this to be a true leisure activity, but you can sandwich sunset between dinner and other nighttime jaunts that are less hectic.
Fun Things To Do in Key West: Take a Sunset Sail
We may have been rebuffed in our attempt to get a great sunset photo from Mallory Square, so we took matters into our own hands. After a quick search on the interwebs machine, we found what sounded like an awesome time: the Wind and Wine Sunset Sail from Danger Charters. All-you-can-drink cocktails, yummy hors d’oeuvres, and an amazing sunset? Yes, please.
For less than $100 per person, we spent several hours on the boat with an entertaining cast of characters and saw one of the best sunsets we’ve ever witnessed. Oh, and we also drank our fill of spirits and destroyed some finger foods, which helped enhance the experience.
The crew of our boat took great care to make sure everyone had a great time, and everyone left with a smile on their face. Except for the shirtless guy who could barely walk when we made it back to the dock. He had more of a grimace. But he had a lot of fun before that, I promise you.
Bottom line: this is definitely something you need to do in Key West. Leisure to the max.
Leisure scale: 10/10
C’mon. It’s a booze cruise on a sailboat in the Florida Keys. With food.
Visit the Dry Tortugas National Park
As amazing as it would be to sleep in every day, sometimes you do have to get up early in the Conch Republic. People of my ilk understand that life doesn’t begin humming in the Keys until noon or so, but some exceptions do apply. Visiting the Dry Tortugas National Park is one of them.
The Dry Tortugas sit 67 miles west of Key West, and the only way to access the park is by boat or seaplane. In our case, we booked a ferry ride on the Yankee Freedom (the park’s official ferry service.) This also meant we had to be on the boat by 7am, which is an ungodly hour for someone such as myself. Miraculously, we made it on time and enjoyed the ride out to the Dry Tortugas, during which we saw a ton of flying fish and several sea turtles.
Once we got to the park, Tiffany and I made a plan of action. We would explore Fort Jefferson and then do some snorkeling. (The ferry provides gear with the cost of the trip.) With only five hours of time before we headed back to Key West, we made a quick tour of the fort and then snorkeled all the way around the exterior of the moat. While we didn’t see much in the way of tropical fish, we did see some yellowtail snapper and barracuda.
I also managed to drop my snorkel and mask in the water as we were getting out and didn’t realize it until we made it to the other side of the island where we stored our stuff. Thankfully, when I got back, the water was so clear that I could see the blue of my mask from a good distance away.
One thing to note about heading to the Dry Tortugas: plan ahead. We booked our ferry tickets several months before we got there. It’s our understanding that the boat can sell out pretty quickly.
Leisure scale: 2/10
Not only did we zoom through the fort, we snorkeled for several hours. I got real tired. Not the most leisurely activity, but highly recommended nonetheless.
Fun Things To Do in Key West: Enjoy the Restaurants
Where do you even begin when talking about the restaurants in Key West? Living in a van makes things a bit more difficult (pesky budget and all), but we managed to have a few great meals that didn’t leave our bank account hurting. Here are two of our favorite, laid-back spots:
Conch Republic Seafood Company
The best way to relax after touring the Dry Tortugas is to stop by the Conch Republic Seafood Company. It’s located just a few blocks away from where the Yankee Freedom disembarks, right on the water. There’s ample outdoor seating, an open-air bar, and tons of great, fresh seafood options on the menu. You’ll run into boat captains, fishing guides, tourists, and locals here.
The atmosphere really captured the Key West vibe. With so many sights, sounds, and smells happening while we sipped cocktails and ate seafood, it made us feel like islanders. Also, the musician that played the night we were there was truly phenomenal. Always a plus.
Pro tip: try the cracked conch. We ended up getting two orders.
Leisure scale: 10/10
Very laid-back atmosphere, great drinks, great food, and a great time.
When we asked around as to the best Cuban-inspired food in Key West, every single person mentioned El Siboney first. Naturally, we had to try it. We visited the location on Stock Island because it was close to our campsite, but both locations are supposedly the same. We tried the Cuban sandwich (amazing) and the daily special (a beef stew served over rice) and both were ridiculously good.
Leisure scale: 8/10
It actually took some hard work to finish our meals. The serving sizes are humongous, and we both ended up with meat sweats.
The first time I went saltwater fly fishing was roughly a decade ago, in the Bahamas. I caught a good number of bonefish and loved every second of it.
Then, I tried to catch a tarpon.
Let’s just say that tarpon and I are not on the best of terms. And I won’t even get started on permit. Regardless of how you fish (fly or spin), spending a day on the water attempting to catch some of the best gamefish in the world is never a bad day.
Leisure scale: 6/10
While I didn’t catch a tarpon (again), I did catch a good-sized jack that gave my arms a workout. I also ended up with bruises in my stomach from fighting and releasing the fish. I’m also a huge baby.
Bonus Info for Van Lifers:
When Tiffany and I decided to spend time in Key West, one of the first things we did was research campgrounds. We thought about trying to camp in a parking spot somewhere on the island, but we heard from a few people that the cops have been cracking down on sleeping in vehicles, so we thought otherwise. We didn’t want all of the fun things to do in Key West be ruined by getting a ticket, or even worse arrested.
Eventually, we settled on Boyd’s on Stock Island. Because we were scared of the campground filling up before we got there, we went ahead and made reservations ahead of time. I’d highly recommend calling ahead. Try your best to get a waterfront site. This was the view we woke up to every morning:
Fun Things To Do in Key West: Final Thoughts
For Tiff and I, our five-day getaway in Key West was a great chance to recharge our creative batteries and enjoy each other’s company. (When you live in a van, that last one is somewhat important.) Overall, as a Man of Leisure, I give Key West my official seal of approval.
Leisure scale: 10/10
There are so many fun things to do in Key West and I love everything about it. I’d move there tomorrow and live the rest of my days as a fly-fishing bum if I could. With or without Tiffany. She’s still not quite a full woman of leisure.
While we tried to cover a wide variety of activities and things to see/do, we know we’re missing some good ones. Leave some more ideas for fun things to do in Key West in the comments!