The Best Worst Cigar I Ever Had

Many years ago, I spent a week under the Mexican sun at Haven Riviera Cancun with friends and family…the kind of trip where everyone’s vibing, everyone’s sipping, and everyone’s on island time…except the lone cigar guy in the group.

Ya boy.

Relegated to the smokers’ area like a feral cat wandering the resort grounds looking for a patch of shade and a moment of peace.

Mexico used to be a cigar paradise, back when cigar lounges were tucked inside every resort like little sanctuaries for the leaf. Dark wood, leather chairs, humidors humming like a choir. But over the last few years, the country tightened its smoking laws with the type of precision only government bureaucrats and angry HOA board members possess.

As a sober smoker, the crackdown hits different.

While everyone else is throwing back Scooby snacks and pounding mini-beers like they’re being timed, I’m over here trying to find a quiet spot to light up and lean in.

Not easy when the government decides smoking is basically sorcery.

In 2023, Mexico rolled out what might be the strictest tobacco laws on earth, no smoking in public. No beaches. No hotel patios. No nothing. Add a total ban on advertising, promotion, or sponsorship, and suddenly those once-romantic cigar lounges get repurposed into juice bars or yoga studios where Chad and Brittany can realign their chakras.

But the trip I’m talking about happened before the purge, back when you could still catch a faint waft of something glorious drifting across a pool deck.

So… back to the beach.

Traveling with a group always turns into a weird sociological experiment.
Everyone’s got their own ideas of paradise:

someone wants adventure

someone wants to shop

someone wants to sit in a chair for seven hours

someone inevitably tries to schedule a group activity at 7:00am

Eventually, we agreed on one shared quest:

Take a catamaran to Isla Mujeres.

We rented golf carts, zipping around the island like a broke version of Mario Kart, and eventually headed toward Tortugranja, a sea turtle sanctuary we’d read about. Educational. Wholesome. Instagrammable. A great story for later.

Except…

It was not what I thought it was.

What we walked into wasn’t a sanctuary.
It was turtle jail.
Different Yards. Different levels of security.
A full-on reptilian penitentiary dressed up as an “animal experience.”

"Clink."

That was the sound, the unmistakable prison-door clank, that echoed behind us as we stepped into Tortugranja. Not the soothing, ocean-sanctuary vibes I had pictured in my head. Nah. This wasn’t “Finding Nemo.” This was Shawshank Redemption.

Instead of a peaceful conservation refuge, it felt like we walked into Turtle County Jail, complete with different Yards.

There was minimum security. The turtles there looked like white-collar criminals…accountants who fudged a few too many tax documents. They were pacing slowly, staring out into the distance like:
"If I ever get outta here, I’m goin’ straight."

Then, there was mid-security; the turtles who might have gotten into a bar fight or sold some questionable seaweed. They gave us that slow, squinty side-eye…like they were sizing us up:
"Yeah, you ain’t from around here, are ya, turista?"

And finally…

Maximum security.
Where the hard cases were. The repeat offenders. The turtles who’d seen some things. Their shells were cracked like they’d been through a few prison riots. These dudes were posted up in the corners like:
"What you lookin’ at, bro? You want the smoke? Didn’t think so."

There was one big-boy turtle, had to be like eighty years old, just staring at a patch of algae on the wall like Red from Shawshank. I swear if he could talk, he would've said,
"Been here since ’74… ain’t leavin’ till they fix the filtration system."

Meanwhile, the juvenile turtles were in another little holding cell, a daycare/solitary confinement combo, splashing around like they were plotting the next great escape.
One tiny turtle kept ramming the side of the tank with the kind of energy that said,
"I may be 4 inches long, but I WILL taste freedom."

I looked around and thought:
This is what happens when Pixar lies to us.
These turtles aren’t out here riding East Australian Currents hanging loose with Crush.
They're serving time.
Hard time.

If there had been a commissary window where you could buy shrimp with turtle stamps, I would not have been surprised.

Our time at Turtle Jail eventually came to an end, and we headed back downtown to do some shopping. You know how it goes…split up, wander, let the sights and sounds tell you what you “need” even though you don’t actually need a thing.

But me?
I did what any brother of the leaf does in a foreign land:
I went hunting for fellowship.

Near the docks, I found a little shop selling all kinds of alleged “Cubans.”
You could practically smell the counterfeits from the doorway.

But I still walked in, like a hopeful romantic.

I gave the boxes a once-over, the way only seasoned smokers do:

Factory codes?

Date codes?

Does the Garantia seal have the QR hologram or does it look like someone printed it off an old Dell inkjet?

Are the bands embossed or flat like kindergarten craft paper?

Are the colors slightly off, like a bootleg DVD cover from 2009?

After bartering over a box of “Siglo IVs,” I walked away.
Seal broken.
Vibes off.
Desperate sales pitch.

Everything inside me screamed, “These ain’t it, brother.”

As we made our way back toward the boat, my wife offered sweet condolences over the missed Cuban opportunity. Before I could respond, my friend, who I didn’t realize had been shadowing me like a cheerful golden retriever, chimed in:

“Bro, don’t even trip. I got you!”

He reaches into his bag and proudly whips out a humidified 5-pack of Cohibas.

“I got these for $30, bro! Absolute steal!”

Someone definitely got robbed…

Still, he was so proud. So genuinely excited to bless me with what he thought was a treasure that I didn’t have the heart to tell him he’d purchased the cigar equivalent of a knockoff Gucci belt in Times Square.

“Let’s smoke these when we get back to the beach,” he said.

Brother…that sounds like a plan.

A few hours later, the sun is dropping behind the shoreline, the breeze is perfect, and he hands me a cigar with the kind of grin that tells you his heart is 100% in the right place.

Within moments, moments, my cigar explodes Yosemite Sam style, unraveling like a cheap party streamer. But I’m committed. I’m trying to cherish his excitement even as this thing tries to fall apart in my lap.

Then I glance over… and he’s staring at his, examining the large canoe forming like he’s witnessing a crime scene. He looks up at me with the most deadpan expression I’ve ever seen him pull off.

“These aren’t real Cubans, are they?”

We both LOST IT.

I’m talking full-on belly laughter…the kind where your lungs tap out and your eyes leak and strangers start checking on you. Two grown men, dying laughing on a beach in Mexico, smoking absolute dog-turds and loving every second of it.

And honestly?

It was the best worst cigar I ever had.

I used to spend so much time with him.
Before sobriety reshaped my life.
Before fatherhood reshaped his.
Before the heaviness crept in and made joy feel suspicious to him.

We’re different now.
Older. Busier.
Weathered by life.

He carries battles he’s not ready to say out loud. Depression and addiction lie; they tell you everyone is against you when, in truth, the people who love you are cheering the loudest.

But when I think of him, I rarely think of the hard stuff.
I think of us on that beach.
Two dudes, sunburned, sand-covered, laughing like kids….smoking terrible fake cigars and not caring one bit.

Just living.
Just being.
Just together.

Continued on my blog due to character limits: https://www.brolocigars.com/blog/the-slowburn-the-best-worst-cigar-i-ever-had