Havana: the most photographed city in the Caribbean, and the hardest to know

It’s 5:42 p.m. on the Malecón, the seafront promenade of Havana, and the waves are coming in off the Florida Straits and breaking against the seawall, throwing spray onto the road. Children are jumping in the spray. An old American Chevrolet — a 1958 Bel Air, candy-pink, in working order — is parked across the road with two men leaning against it talking. The sun is dropping toward the horizon over the harbour. The buildings on the Malecón are, mostly, in a state of slow, beautiful collapse — facades half-fallen, balconies fenced off, paint flaking in textured ribbons. This is Havana, and this is, despite everything, one of the most visually striking cities I have walked in.

Why I keep coming back

I’ve been to Cuba four times since 2010 — before the brief 2015–2017 Obama-era opening, during the boom in American visitors, and after the U.S. restrictions returned. Each visit, the city has been visibly more challenged: shortages, blackouts, queues, the dual-currency system reforms, the post-pandemic economic crisis. Each visit, the resilience and the warmth of the Cubans I have met has been the strongest impression I took home.

Havana’s architecture is the surface attraction — one of the largest collections of 16th–20th-century Spanish-colonial, neoclassical, and Art Deco buildings in the Americas. The food has improved significantly in the past decade since the paladar (private restaurant) reforms. The music is permanent. The political and economic realities, particularly in the past three years, are difficult and visible.

Where to base yourself

Habana Vieja for the colonial-old-town walk-around. The most-photographed but also the densest cluster of restored buildings.

Centro Habana for the working-residential neighbourhood feel; gritty, real, walking distance to Old Havana.

Vedado for the wide tree-lined 20th-century neighbourhood, with the Hotel Nacional, the Malecón, and the Plaza de la Revolución.

A casa particular — a private homestay — is, in my view, the right choice in Cuba over the state-run hotels. You’ll eat better, sleep better, and pay your money directly to a Cuban family.

What to actually do

Walk the Malecón at sunset. Free, the daily ritual of the city.

Walk Habana Vieja’s four main plazas. The Plaza de la Catedral, Plaza Vieja, Plaza de San Francisco, Plaza de Armas. The architectural concentration is extraordinary.

Visit the Museo de la Revolución. Housed in the former presidential palace; from the Cuban Revolutionary perspective.

Visit the Museo Nacional de Bellas Artes. Two buildings — the Cuban art building has the genuine surprise of the 20th-century Cuban modernist painters (Wifredo Lam in particular).

Listen to live music. Buena Vista Social Club–style son cubano at La Bodeguita del Medio (touristy), the cheaper local at the Casa de la Música in Centro Habana, the modern at Fábrica de Arte Cubano (FAC, a multi-arts space in Vedado).

Take a 1950s American car for a ride along the Malecón. The taxi almendrones (the big-American-car taxis); around US$30 for an hour. The cars are operated by Cuban mechanics doing extraordinary work keeping pre-1960 American vehicles running.

Day trip to Viñales. Two hours west; the tobacco-growing valley with its rounded mogote limestone hills, ox-pulled ploughs, and small tobacco farms. The classic Cuba beyond Havana.

Where to eat

A paladar — a private restaurant — is where Cuban cooking is at its current best. State-run restaurants are mostly poor.

La Guarida (Centro) — The iconic paladar; expensive, in a beautifully tatty restored townhouse used in the film Strawberry and Chocolate. El Cocinero (Vedado) — Modern Cuban, next door to FAC. Doña Eutimia (Old Havana) — Reliable Cuban food on the Plaza de la Catedral. Atelier (Vedado) — Set menu, refined. O’Reilly 304 — Small-plate Cuban-Spanish; popular. Local Cuban breakfast: at your casa particular, the morning fresh fruit and Cuban coffee will be among the best of your trip.

When to come

November through April is the dry season; pleasant temperatures.

May through October is hotter, more humid, and hurricane-affected.

Practical notes

• Visa: A ‘tourist card’ (in practice a visa) is required; most travel agencies and airlines arrange it.
• Money: The Cuban peso (CUP) is now the standard currency. The previous dual-currency system (with the CUC) was eliminated in 2021. The official exchange rate and the street rate differ significantly; ask locally before exchanging.
• Cards: U.S.-issued cards do not work in Cuba (and may never; the Trump-era restrictions remain). Cards from other countries work at some hotels. Carry hard currency (euros or USD) for the major part of your trip’s funds.
• Internet: Slow, limited, expensive. ETECSA hotspots in public squares; new mobile data plans are improving but unreliable. Many Cuban families use Wi-Fi cards purchased from ETECSA.
• Power cuts: A real feature of the past two years. The grid has had significant problems. A flashlight is useful.
• Shortages: Basic goods (food, medicine) have been intermittent. Cubans have adapted with extraordinary patience. As a visitor, your hard-currency-stocked hotel or paladar will mostly insulate you, but be aware of the larger reality.
• Sensitive topics: Discussing politics openly is sometimes complicated; many Cubans will speak freely, others won’t. Take cues from your hosts.

A final thought

Havana, more than any other city in this guide, is impossible to write about without acknowledging the political and economic realities surrounding the visit. The 60+-year U.S. embargo, the post-Soviet economic collapse, the post-Castro political transition, the past two years of acute shortages — all are visible and they shape the experience.

The city remains, despite all of this, one of the most architecturally distinct and culturally resilient in the Americas. The Cubans you’ll meet will be warm, curious, and direct in a way that surprises North American visitors. The music is everywhere. The food has gotten genuinely good in the past decade. The cars work.

Go, if you can, with a long-form mindset. Stay in a casa particular. Spend money directly with Cubans (paladares, private taxis, casa particulares, music venue tips). Talk to locals. Walk the Malecón at sunset. Acknowledge the difficulty without pretending it isn’t there. The country has been through a difficult century; the visit is part of one form of support for the people who live there. Three or four nights minimum in Havana; six is better.