Walk the loop
Three hours, one solid loop.
Start at Plaza de la Catedral, drift south to Square of the Angel, west to Calle Cuarteles for the galleries, then through Calle Cárdenas, finishing at El Capitolio. Hire a classic car for the last fifteen minutes and ride down Paseo del Prado for the postcard. One solid hour of photographs, one hour of wandering, an hour for a coffee somewhere along the way.
Old Havana on foot
Old Havana, end to end.
Start at Plaza de la Catedral right after sunrise, when the square is empty and the light is gold. Walk south to Square of the Angel, then drift west to Calle Cuarteles. Loop back through Calle Cárdenas for the street-art and Art Nouveau details, finishing at El Capitolio. With a polite "two minutes please," you can usually get a clean shot at the Abbey Road crossing on your way past.
Morning → Sunset → Night
The full day, three acts.
Morning: the Half-Day route, ending at El Capitolio around late morning. Lunch nearby — Al Carbón is a good call.
Afternoon: walk down Paseo del Prado, then hire a convertible for an hour. Cover Doors of Havana and drive past the Malecón seawall.
Late afternoon: cross the tunnel to Morro Castle for the lighthouse against a softening sky, then return for sunset on the Malecón. End at La Guarida for dinner, or Yarini Habana for cocktails.
Day two: slow it down
Two days, with a pace you can actually keep.
Day one — the Full-Day route above.
Day two — a slow morning wandering Cine Cuba and Malecón 663. End with the 9 PM cannon ceremony at Morro Castle — the perfect quiet closer to a busy day.
Add the colour: Fusterlandia + Hamel
Three days, the works.
Days one and two — the Two-Day route.
Day three — half-day at Fusterlandia in the morning (light is best before noon, crowds still light), then back for lunch and a slow afternoon. If it is a Sunday, finish at Callejón de Hamel for the rumba — the most authentic ending I can imagine.
Trust the light
The photoshoot weekend, full focus.
Day one — 7 AM Plaza de la Catedral. Golden-hour Capitolio. 4:30 PM Doors of Havana & Calle Cárdenas. Sunset and dinner at La Guarida (rooftop reservation), and stay for blue hour from the upper terrace.
Day two — 6:30 AM Malecón for the empty seawall. 9 AM Square of the Angel before tour groups arrive. Midday: outfit change & real lunch. 4 PM convertible ending at Calle Cuarteles. Sunset at Morro Castle, lighthouse turning on as you leave.
Day three — Fusterlandia at 9 AM. If Sunday, Callejón de Hamel at noon for rumba. Closing dinner anywhere you want; you have earned it.
Cinematic moments only
The romantic trip.
Two or three days, designed around the most cinematic moments. Sunrise on a rooftop. Slow lunch at a paladar. Late afternoon at Square of the Angel — the most intimate plaza in the city. Sunset at Morro Castle, behind the grass on the far side, away from the souvenir vendors (this is where I bring the nervous gentlemen with suspicious hands in their pockets). Dinner at La Guarida if you can book it.
Anniversary version: add a Flying Dress photoshoot on the Malecón at golden hour.
Pace over route
With kids in tow.
Mornings only, finish before the heat. Best stops for younger children: Plaza de la Catedral (open space to run), the convertible ride (a real hit), the Malecón at sunset (sea breeze, room to wander), and Morro Castle at 9 PM for the cannon ceremony. Avoid Calle Cárdenas at busy hours and any rooftop without a guardrail you trust. Snacks and water in the bag.
Time it for a Sunday
For music lovers.
Time your trip so a Sunday afternoon lands on the Callejón de Hamel rumba. Build the rest around: Yarini Habana for cocktails and a band, Fangio Habana for jazz nights, and Fábrica de Arte Cubano (FAC) for the multi-room music-and-art evening that has become the city's signature. King Bar to dance at the end. You will not sleep much; you will not regret it.