Seven Days in Havana: An Unfiltered Travel Journal
You go to Havana expecting classic cars and mojitos. You get those. You also get a reality check about what travel means when your phone is basically a brick and your credit card is a fancy bookmark.
Day 1: Arrival and Immediate Confusion
Jose Marti airport looks like it was last renovated when the Soviets were still funding things. Immigration can run 52 minutes, so pace yourself. The pink tourist card costs $75 at the airline counter — the going rate for US travelers, though people report paying anywhere from $50 to $100. Have your casa particular arrange a taxi, because there's no Uber. There's no Lyft. There's basically no app-based anything.
The drive from the airport is your first introduction to the cars. Not just one or two vintage Chevys for photo ops. Hundreds of them. Thousands. They're not museum pieces — they're how people get to work. A turquoise '54 Chevy Bel Air pulls up beside you at a red light, its driver blasting reggaeton. Welcome to Havana.
The casa particular on Calle Obispo is run by Marta, a retired teacher. Room: $35/night with breakfast. Clean, with working AC (crucial) and a tiny balcony overlooking the street. Marta hands you a paper map. "Google Maps doesn't work well here," she says. She isn't wrong.
Day 2: Old Havana by Foot
Breakfast at the casa: eggs, fresh mango, toast, and the strongest coffee in the Caribbean — made in a little stovetop percolator that looks older than the building itself.
Spend the entire morning in Habana Vieja. Four plazas. Countless colonial buildings. The thing about Old Havana is that it's a UNESCO site that hasn't been over-restored. Some buildings are gorgeous and freshly painted. The building next door might be literally falling down. That contrast is everywhere, and it's weirdly beautiful.
Plaza de la Catedral at 8AM: almost empty. By 10AM: packed with tour groups. Get there early.
Lunch: a paladar off Calle O'Reilly. Ropa vieja (shredded beef), rice, beans, and a beer. Total: about $8. The ropa vieja arrives rich with tomato, slow-cooked until the beef falls apart at a glance.
Afternoon: walk the Malecon from Old Havana toward Vedado. It's 8 km total. Most travelers make it about 3 km before the sun and humidity send them into a bar. A cold Cristal beer (the local lager): $1.50.
Day 3: The Hemingway Circuit
Start at El Floridita. Frozen daiquiri: $6. Hemingway's bronze statue sits at the end of the bar, and yes, the photo is practically mandatory. The daiquiri is legitimately good — limey, cold, not too sweet.
Walk down Obispo to La Bodeguita del Medio. Mojito: $5. The walls are covered in signatures from every tourist who's ever visited. The mojito itself? Just okay — the street bars pour better ones.
Here's the honest take: skip the Hemingway trail after the two bars. Finca Vigia (his house outside the city) is interesting but requires a taxi and half a day. Unless you're a serious Hemingway fan, spend that time at Fabrica de Arte Cubano instead.
Day 4: Callejon de Hamel and Centro
Sunday. This is the day.
Reach Callejon de Hamel at 11:30AM and stake out a spot near the front. By noon, the rumba starts. Three drummers, two dancers, and a crowd that forms a circle and takes turns dancing in the center. The drumming echoes off the painted walls. Someone hands you a cup of rum. Don't ask where it came from. It's terrible rum. It's perfect.
The rest of Centro Havana is rougher than Old Havana. Buildings in serious disrepair. But it's real life. Kids playing baseball in the street. Dominoes on the sidewalk. A woman selling pizza slices out of her kitchen window for 5 pesos.
It's easy to get completely lost around Calle Neptuno on the way back — the paper map is useless in the maze of similar-looking streets. Ask an old man for directions and he might walk you to the corner and point. "Derecho, derecho" — straight, straight. Cuban hospitality in action.
Day 5: Classic Car Tour and Revolution Square
Give in to the tourist thing. Negotiate with a driver at Parque Central: $40 for a 1.5-hour tour in a gorgeous mint-green 1955 Buick Century convertible.
Revolution Square is massive and feels Soviet in a way few travelers expect. The Che Guevara mural on the Interior Ministry building is enormous. The Jose Marti memorial tower (109 meters) dominates the skyline. There's an odd emptiness to the place — it was designed for rallies of a million people, so on a regular Tuesday it feels like an oversized parking lot.
The drive through Vedado is the highlight. Mansions from the pre-revolution era, some immaculate and some in ruins, line wide avenues under canopies of trees. A good driver points out which ones had been embassies, which are now government buildings, and which are just slowly returning to nature.
Day 6: Fabrica de Arte Cubano
Sleep until noon. On purpose. FAC doesn't open until 8PM on Thursdays.
Arrive at 9PM. Entry: $2. This place is unreal. Four floors of a converted factory with art installations, photography exhibits, a film screening room, two bars, a stage with live jazz, and a crowd that's equal parts local artists and foreign travelers.
Stay until 1AM. Total bar tab: $15. The cocktails are actually good. The music shifts from jazz to electronic to Cuban fusion. A photographer's exhibit about daily life in Havana will make you see the past five days differently.
This is where it clicks: Havana isn't a museum. It's not frozen in time. The vintage cars and colonial buildings are the backdrop, but there's a creative pulse here that's completely contemporary.
Day 7: Last Day Wander
Buy rum at a local shop. Havana Club Anejo 7 Anos: $12 per bottle. A box of Cohiba cigars at La Casa del Habano: $280. These are the prices you pay for authentic products. The street prices are lower, and the products are fake.
Take a final walk through Old Havana. Duck into the Plaza Vieja microbrewery for a last beer. Sit in the square and try to memorize it — the colors, the sound of someone practicing trumpet from a second-floor window, the occasional vintage taxi rolling past.
Final dinner at the casa: Marta cooks lobster. Tail, claws, rice, black beans, and a salad. $10. She sits with you, and the conversation stumbles happily through broken Spanish and a few words of English. She asks if you'll come back. Say yes. Mean it.
Would You Go Back?
Absolutely — and there's a smarter way to do it.
Bring more cash. It's easy to run low by Day 5 and spend the rest of the trip being careful. Pack twice what you think you'll need. For more insights, check out our complete guide to Havana. For more insights, check out our [Havana vs Cartagena](/blog/havana-vs-cartagena-caribbean-comparison) comparison.
Skip the Hemingway tourist circuit and spend that time in the neighborhoods — Centro, Vedado, the Malecon at different times of day.
And stay longer. A week isn't enough. Havana doesn't reveal itself on a schedule. You need time to get lost, time to sit, time to let the city come to you.
Damage Report:
Total spent: approximately $480 for 7 days
Best meal: Marta's lobster dinner ($10)
Best experience: Callejon de Hamel Sunday rumba (free)
