This is the most common scam in Havana and it happens on Calle Obispo approximately every fifteen minutes. Someone approaches you — friendly, well-dressed, often excellent English — and strikes up a conversation. Where are you from? First time in Cuba? You must try the real Cuban food, not the tourist places. Let me show you somewhere my family goes. You walk with them, they take you to a restaurant where the prices are double what they should be, and they receive a commission from the owner for delivering you. You pay, they disappear, the food is mediocre.

A related variant: they tell you the museum / restaurant / bar you’re heading to is “closed today” and offer to take you somewhere better. The original place is invariably open.

A woman with a baby approaches and shows you an empty milk can — the baby needs formula, she has no money. If you agree to buy it, she takes you to a particular shop nearby where the formula costs $15–20. You pay. She leaves with the formula, returns it to the shop owner who splits the cash with her, and the can goes back on the shelf for the next tourist. It’s a well-run loop and the sympathy angle is deliberately chosen because it’s the hardest to reject.

Someone hands you a flower, a cigar, a small bottle of rum, or takes your photo without asking. Then they ask for payment. The same applies to the women in traditional Cuban dress near Plaza de la Catedral — a photo with them costs money, and the amount is whatever they can negotiate after you’ve already taken the shot and feel obligated. A musician who plays a song at your café table and then presents a CD for purchase is a softer version of the same thing.

None of these are illegal. They’re all consent-adjacent — the service is delivered before the price is discussed.

This is the simplest and most widespread of all Cuba’s tourist money issues. You hand over a note, the vendor or driver counts back change quickly and confidently, and the amount is wrong — sometimes by a small margin, sometimes significantly. It works because tourists are often handling unfamiliar notes in a hurry, are distracted, or feel awkward slowing down to count carefully. The technique is usually a fast hand, an extra note folded behind the real ones, or just counting quickly and hoping you don’t check.

It’s not unique to Cuba, but the all-cash environment and unfamiliar currency notes make it more effective here than in countries where card payments are normal.

People approach tourists offering to exchange foreign currency for Cuban pesos at a rate “better than the bank.” Sometimes the rate offered is genuinely good; sometimes it’s not; sometimes the notes handed over are counterfeit or are old, demonetized bills that look like current currency to someone unfamiliar. The informal exchange market has become less common since Cuba unified its currency in 2021 but still exists, particularly near José Martí Airport and in Old Havana.

You order from a menu with clearly listed prices. The bill arrives and the numbers are higher — sometimes slightly (a cocktail priced at $4 becomes $6), sometimes significantly. There are several versions: the “tourist menu” with different prices from the “local menu”; items added to the bill you didn’t order; covers or service charges disclosed verbally at the end rather than listed anywhere visible; and the straightforward miscalculation that always runs in the restaurant’s favour.

Tourist-heavy restaurants around Parque Central, Plaza Vieja, and the Malecón are most likely to do this. It’s less common but not unknown at legitimate paladares.

Linked to the Friendly Stranger scam above, but worth its own entry. Certain Havana restaurants pay street-level commission to anyone who brings in foreign tourists — typically 10–20% of the bill. The person who leads you there might be a stranger, a taxi driver, your casa’s cleaner, or someone who presents themselves as a local guide. The restaurant is often fine. But you’re paying inflated prices to cover the commission markup, and you weren’t choosing the place freely.

The taxi from José Martí International Airport to Old Havana should cost $25–30 for a standard private taxi. It’s a fixed-rate route and the price is reasonably consistent among legitimate drivers. But touts inside and immediately outside the arrivals hall will quote $40, $50, or more to anyone who looks uncertain — which is everyone on their first arrival. There is no meter. The negotiation happens before you get in.

The inverse exists too: a driver quotes $25, you agree, and when you arrive they claim they said $25 per person, not per car. This happens with groups.

Your taxi driver — or someone who approaches you at the bus station — helpfully tells you that your hotel or casa particular has closed, burnt down, flooded, or is fully booked. They know a better place. This “better place” pays commission, often has higher prices, and is absolutely not where you intended to go. The original accommodation is almost always fine and open.

This is one of the more brazen scams because it requires a direct lie and relies entirely on you not being able to verify it quickly. Without mobile data in Cuba, many travelers can’t call ahead to check.

Classic convertible car tours of Havana are legitimately excellent and genuinely worth doing. The scam is in the pricing: approaching drivers in tourist areas will quote $50–80 per hour for a car that should cost $35–45. The car, the driver, the route, and the experience are identical — the only thing that changes is who sold you the trip and what their margin is.

Relatively uncommon but worth knowing: a small number of casa listings — particularly on less-regulated booking platforms — show photos of a nicer room or property than the one you actually get. The photos may be of a different room in the building, a neighbouring property, or simply taken in unusually flattering conditions with outdated information. On arrival you’re shown a different room that’s technically habitable but not what the images implied.

This is one of Cuba’s most established tourist scams and it runs at scale. Men — often near major squares in Havana — approach tourists offering “genuine Cohibas” or “factory-second Montecristos” from a friend who works at the factory. The story is convincing. The packaging can look authentic. The cigars are almost always fakes — lower-quality leaf stuffed into fake branded boxes, often dried out, poorly constructed, and nothing like the real product.

A box of 25 “Cohibas” bought on the street for $15–20 is fake. The same box at a state Casa del Habano for $120–200 is the real product. If someone approaches you with cigars, assume they’re fakes regardless of the story.

Jineteros (literally “jockeys”) is the Cuban term for street hustlers who attach themselves to tourists for financial benefit. The encounter typically starts genuine — a friendly conversation, an offer to show you around, maybe a short dance lesson or music performance. Over the course of hours, the relationship shifts: there are requests for small amounts for drinks, food, transport, eventually a direct ask for money “for the family.” The time investment is considerable on both sides.

This isn’t always a scam — some jinteros provide genuinely good local company and earn a fair fee for their time. But the dynamic of the relationship is one where you’re being worked toward a financial destination, and the bill at the end can be significantly larger than expected.