Havana & Cuba: Classic Cars, Colonial Grandeur & the Caribbean's Most Intoxicating City

Havana is the world's greatest living museum of mid-20th-century urbanism — a city frozen, in certain respects, at a moment just before the revolution of 1959, where Baroque Spanish colonial churches, Neoclassical municipal palaces, Art Deco apartment towers, and the extraordinary American Modernist buildings of the 1940s and 50s coexist in a state of dramatic, photogenic decay and ongoing restoration that is found nowhere else on earth. The Malecón — the 8km seafront promenade stretching from the old city to the Vedado residential district — is the social spine of the city: at sunset, families gather on the seawall, musicians play for anyone who stops to listen, and the famous fleet of vintage American cars — Chevrolets, Buicks, Fords, Plymouths, and Chryslers from the 1940s and 50s, kept running through Cuban mechanical ingenuity and Soviet engine parts — cruise slowly past in shades of pink, turquoise, and canary yellow.

La Habana Vieja: UNESCO World Heritage Old Town

Old Havana (La Habana Vieja) was designated a UNESCO World Heritage Site in 1982 — one of the finest ensembles of colonial Spanish architecture in the Americas, centred on four great plazas: Plaza de Armas (the oldest, dating to the 1520s), Plaza de la Catedral (home to the 18th-century Havana Cathedral with its asymmetric twin towers), Plaza Vieja (a restored 18th-century residential square), and Plaza de San Francisco de Asís (dominated by the former Franciscan convent, now a concert hall). The Office of the City Historian (habanacultura.ohc.cu), led for decades by the remarkable Eusebio Leal Spengler, has overseen a meticulous restoration programme since the 1990s, funded by hotel and restaurant revenues within the historic core.

Where to Stay

Gran Hotel Manzana Kempinski La Habana (kempinski.com/havana) — opened in 2017 in a beautifully restored 1910 Beaux-Arts building on Parque Central — is the finest hotel in Havana and the first international luxury brand in Cuba since the revolution: 246 rooms and suites, a rooftop pool with views across the old city's terracotta rooftops to the Malecón, and a level of finish and service not previously available in Cuba. Suites from $600/night.

Iberostar Grand Packard (iberostar.com) on the Paseo del Prado, facing the Malecón, is the city's second major international luxury property: a restored 1920s building of great elegance with a spectacular rooftop bar. Rooms from $250/night.

For the authentic Old Havana experience, the city's finest privately owned casa particular (bed and breakfast) operators — bookable through Airbnb — are concentrated in La Habana Vieja and Vedado, and many are housed in extraordinary Art Deco or colonial buildings with high ceilings, mosaic floors, and genuine Cuban hospitality.

The Music: Son, Salsa & the Buena Vista Legacy

Havana's musical culture — rooted in the fusion of Spanish and West African traditions that produced son cubano, the rhythmic foundation of all Latin music — is one of the city's greatest gifts to world culture. The Buena Vista Social Club (buenavistasocialclub.com), the 1997 project that introduced Compay Segundo, Ibrahim Ferrer, and Omara Portuondo to international audiences, sparked a global Cuban music revival; the recording sessions took place at EGREM's Estudio Areito, still operating in Central Havana. Live music fills the colonial courtyards of La Habana Vieja from afternoon onwards — the Casa de la Música, the Fabrica de Arte Cubano (in Vedado), and the Casa del Son are the principal venues.

Ernest Hemingway's Havana

Hemingway lived in Havana for most of the period 1939–1960 and remains the most famous foreign resident in the city's history. The Hotel Ambos Mundos (room 511, where he wrote For Whom the Bell Tolls) and La Floridita bar (where the daiquiri was supposedly perfected for him) are tourist sites; the Finca Vigía (hemingwayhavana.com) — his 15-acre farm outside the city, now a state museum — is the authentic Hemingway pilgrimage site, with the house preserved exactly as he left it.

Getting There

José Martí International Airport (HAV) in Havana receives direct flights from Mexico City (Aeroméxico, Interjet), Madrid (Iberia), Paris (Air France), London (Virgin Atlantic seasonal), Toronto (Air Canada), and several Latin American cities. US citizens may visit Cuba under specific licence categories; travel regulations continue to evolve and should be verified at the time of booking.

Reference Links:

- Cuba Tourism: cubatravel.cu

- Gran Hotel Manzana Kempinski: kempinski.com/havana

- Buena Vista Social Club: buenavistasocialclub.com

- Havana cultural heritage: habanacultura.ohc.cu

- Finca Vigía Hemingway Museum: hemingwayhavana.com

- Iberostar Grand Packard: iberostar.com