A Gringo in Cuba…

Where to Stay: Finding Home in the Ruins

Havana is a fever dream.
A crumbling postcard from another century — grand colonial mansions held together by salt, rust, and defiance. It’s beautiful and battered, like a boxer past his prime but still throwing punches. Choosing where to stay in this chaos can feel overwhelming, but here’s a breakdown that might help — and a gentle nudge in the direction I’d take.

Option 1: Old Havana (Habana Vieja)

This is the classic image — cobblestone streets, vintage cars, mojitos at El Floridita, and music on every corner. It’s incredibly picturesque, especially for first-timers.
But know this: it’s also hectic, heavily touristed, and crawling with hustlers. Everyone’s got a cousin who can sell you cigars. Everyone wants a tip. It’s stunning, yes — but it’s the Cuba you share with thousands of others.

Option 2: Centro Habana

A little west of Old Havana, this area can look rough around the edges. Buildings are more decayed, the streets louder, the energy more raw.
It can feel chaotic and even intimidating at first glance — but it’s real. That said, it’s loud as hell, and not the most relaxing base if you like your sleep.

Option 3: Vedado (My Pick)

This is where Havana breathes. Wide streets lined with faded mansions, leafy trees, and a surprising calm by city standards. It's a little further out, but that’s a feature, not a flaw.

I stayed here and loved it. It forced me to walk the Malecón — that weathered stretch of seaside concrete that runs the length of the city — all the way through Centro and into Old Havana. As a photographer, it was a gift. Every block had a story.

Vedado is where you’ll find the soul of Havana in the quiet moments. And if you squint, you might catch a glimpse of what this city used to be — and what it stubbornly refuses to stop being.

I stayed with a truly amazing couple here — Arnaldo and Julia. They treated me like a long-lost son, with warmth, generosity, and damn good coffee. They also helped arrange airport transfers and even changed money for me at a fair rate — which leads us right into the next survival skill every gringo needs.

Safety, Scams, and the Money Maze

Let’s tackle the obvious:

Is Cuba safe? And do they hate Americans?

First — yes, Cuba is incredibly safe, especially compared to many parts of Latin America. You won’t see much visible police or military presence, but don’t let that fool you. There are eyes everywhere. A dictatorship with secret police and harsh consequences has a way of keeping petty crime in check.

That means you can wander the streets solo — camera in hand, sun on your back — without looking over your shoulder. I never once felt threatened or stressed out. But that doesn’t mean you should act like a clueless idiot.

• Don’t flash wads of cash.

• Don’t get drunk and wander down dark alleys.

• Take a taxi at night.

• And maybe, just maybe, don’t brag about your crypto portfolio in public.

Scams? Oh, absolutely. Especially in Old Havana.
If someone calls you “my friend” and asks where you're from, there’s a 99% chance they’re about to lead you to an overpriced bar, sell you fake cigars, or hit you with a sob story that ends in a bill. Just smile, nod, and keep walking.

Also worth noting: there are a lot of working girls in Centro and Old Havana. They’ll come right out and ask if you’ve got a hotel or casa. Don’t engage. At best, it’s a setup. At worst, it’s a crime. Either way, not worth the risk of getting robbed or detained.

Now — about that U.S.-Cuba tension.
You’d think with all the decades of embargoes and hostile headlines, there’d be animosity toward Americans. But nope. Not even close. Cubans are warm, educated, and shockingly good at separating politics from people. Everyone’s got a cousin or sibling in Miami. You’ll be welcomed with curiosity, not contempt.

The Real Headache: Money

This is where things get tricky. If you’re American, your credit and debit cards will be completely useless in Cuba. They will not work at all. There is no backup plan, no exception. You need to bring cold, hard cash.

The silver lining? U.S. dollars are widely accepted — and often preferred. Cuba’s economy is in freefall, inflation is sky-high, and the dollar has become a kind of unofficial second currency. It’s ironic, really, but it works in your favor.

Here’s the deal:

• Bring at least $1,000 per week of travel. More if you’re not booking everything in advance.

• Book your lodging and as many experiences as possible ahead of time on Airbnb.

• If you can, bring euros too — they sometimes fetch an even better rate.

I had the luxury of carrying a Mexican credit card as backup, but you probably don’t. So bring more cash than you think you'll need.

Now, about exchanging money...

The official exchange rate is a joke — currently around 24 pesos to the dollar.
The real rate on the street is closer to 370 to 1. That’s not a typo. That’s inflation, baby.

Do not — I repeat, do not — exchange money at state banks or government exchange houses. You’ll get absolutely fleeced.

But also — don’t change money with random strangers on the street. That’s a fast track to getting scammed, robbed, or handed counterfeit bills.

Your best bet? Your Airbnb host.
They’ll often offer a solid rate and a safe transaction. And pro tip: only exchange small amounts at a time. Once your dollars become pesos, it’s damn near impossible to trade them back.

The State-Owned Trap: What They Don’t Tell You About Famous Spots

Here’s something that seriously irked me — and it will probably piss you off too once you catch on: most of the “famous” bars, restaurants, and hotels in Cuba are state-owned. Specifically, many are operated by government or military entities under the guise of tourism.

That mojito you’re sipping at a “historic” bar in Old Havana?
Yeah, that $9 drink is padding the pockets of a regime that’s hoarding foreign currency like gold bars in a bunker.

You’ll notice menus often list prices in both Cuban pesos (CUP) and U.S. dollars, but then — in tiny fine print at the bottom — say something like:

“Peso payments accepted from Cuban nationals only.”

Translation? They’ll try to force you to pay in dollars, even though the menu says otherwise. It’s not just shady — it’s a deliberate tactic. These state-run places are stockpiling foreign currency by manipulating tourists into thinking they can’t pay in the local coin.

I had the distinct displeasure of this game while grabbing lunch in Viñales.
They pulled the “no pesos for foreigners” move. But I speak Spanish, and I wasn’t having it. I fought tooth and nail, argued with the waiter like a full-blown Karen with a mission — and finally got them to take my pesos at the actual printed rate.
The difference? Massive.

If you don’t speak Spanish? Good luck, buddy. You’re going to need it.

The core issue here is that they price in pesos using the official exchange rate (24:1) — which is total fiction. In reality, the street rate is around 370:1, so if they charge you in dollars, you’re paying 10-15x more than a local would using pesos.

The Bottom Line

• Avoid state-run places like the plague.
  If it’s a “must-see” spot in every travel blog or it’s tied to a historic figure (hello, Hemingway bars), assume the government owns it.

• Always ask if you can pay in pesos.
  If they say no, walk. Or argue — up to you.

• Support private restaurants and paladares.
  These are locally owned and legally independent from the government. Not only are they cheaper and more ethical, they’re usually better, too.

Cuba’s full of great food and drink — just don’t let your dollars blindly bankroll a system that’s playing tourists like suckers.

Getting Around: Classic Cars and the Cuban "Uber"

Forget Uber, Lyft, or any of the modern comforts you’re used to. In Cuba, there’s only one ride-hailing app you need: La Nave.

It’s the Cuban answer to Uber — except instead of a Prius, you might get scooped up in a '58 Chevy Bel Air or a boxy Soviet-era Lada with no seatbelts and vibes for days. It’s clunky, old-school, and kind of amazing.

A few quick tips:

• The app works pretty well, but you’ll need internet access to request a ride (so that SIM card and VPN come in clutch here).

• It’s all paid in cash, so keep small bills handy.

• Walk during the day if the heat isn’t brutal — it’s the best way to soak in the soul of Havana. But after dark?
  Don’t be a hero. Just open La Nave, hop in a classic car, and let those squeaky shocks carry you home.