Havana

Habana Vieja, the UNESCO-listed old town, is the city's treasure — one of the great colonial centres of the Americas, a dense quarter of cobbled streets and squares being painstakingly restored amid the romantic decay. Four plazas anchor it: the Plaza de la Catedral, framed by a beautiful baroque cathedral and colonial mansions; the Plaza de Armas, the oldest square, leafy and lined with second-hand book stalls and the former governors' palace; the harbour-side Plaza de San Francisco with its old basilica and merchant houses; and the restored, pastel-coloured Plaza Vieja, ringed by cafés and a craft brewery. Between them wind streets full of museums (the Museo de la Ciudad), old pharmacies, art galleries, and the legendary Hemingway bars — La Bodeguita del Medio for a mojito and El Floridita for a daiquiri. The pedestrianised Calle Obispo buzzes with shops and music. It's a place to wander without a plan, glass of rum or coffee in hand, letting the atmosphere carry you.

No experience captures Havana like the Malecón, the broad seafront esplanade and seawall that curves for some eight kilometres along the city's northern edge, from the old town past Central Havana to Vedado. By day it's a windswept promenade where anglers cast lines into the strait; by late afternoon and evening it becomes the city's living room — couples, families, musicians, rum-drinkers and dreamers gathering along the wall to watch the sun set over the water and the waves burst spectacularly over the parapet on rough days. A drive or a walk along it, especially at golden hour, is the quintessential Havana moment. Across the harbour mouth stand the imposing 16th- and 18th-century Spanish fortresses — the Castillo de los Tres Reyes del Morro with its lighthouse, and the great La Cabaña fortress, where a costumed cannon-firing ceremony (the cañonazo) takes place every night at nine, a popular evening outing with views back across the water to the lit-up old city.

Beyond the old town, Havana reveals more of itself. The famous fleet of brightly coloured 1950s American cars — Chevrolets, Buicks, Fords, kept running for seventy years through resourceful, constant mechanical improvisation — works the streets as shared taxis and tourist convertibles; a dedicated open-top ride along the Malecón is a paid tourist activity in its own right (agree the price and route beforehand) rather than a free extra, and is worth booking through a reputable operator given the range in vehicle condition. The grand domed Capitolio, modelled on Washington's, marks the edge of the old town beside the Gran Teatro. To the west, Vedado is the leafy, early-20th-century district of broad avenues, faded mansions and Art Deco and modernist landmarks — the storied Hotel Nacional on its bluff above the sea, the Revolution-era hotels of La Rampa, the university, the vast Colón Cemetery and the Coppelia ice-cream park beloved by Habaneros. Further out, the immense Plaza de la Revolución, ringed by government ministries and the famous steel mural of Che Guevara, and the playful tiled fantasy of Fusterlandia in the suburb of Jaimanitas, round out the city's range, from grand to gritty to whimsical.

Havana's deepest pleasures are sensory. Music is everywhere — son and salsa, the rumba of Callejón de Hamel on Sundays, the trova in the bars, the legacy of the Buena Vista Social Club kept alive in venues across the city; there is live music in some plaza or bar at almost any hour, and dancing comes naturally. The city is also the home of Cuban rum and cigars: the Havana Club rum museum and the city's bars pour mojitos, daiquiris and Cuba libres, while the hand-rolling of the world's most famous cigars can be seen at the cigar factories and bought in the official shops. Hemingway's Havana is a thread for many visitors — beyond his bars, his beautifully preserved home, Finca Vigía, on the city's outskirts, and the fishing village of Cojímar that inspired The Old Man and the Sea, make rewarding excursions. Add the city's art scene, the private paladar restaurants serving creative Cuban cooking, and the option of staying in a casa particular (a family homestay) for a closer connection to Habaneros, and Havana becomes a city you feel as much as see.