Cartagena vs Havana

How do Cartagena and Havana compare?

The Caribbean's two great Spanish-colonial walled cities, both UNESCO-listed and both still very much lived in. Cartagena is the polished one — Old City pastel facades, Getsemaní street art and rooftop bars, Café del Mar drinks on the wall at sunset, palenqueras balancing fruit baskets, and Rosario Islands day-boats running every morning from the marina. Havana is the slower, more weathered one — Habana Vieja's UNESCO core peeling beautifully, Malecón crashing waves against the seawall, classic 1950s Chevys still running on diesel, paladar dinners in private homes, and Bodeguita del Medio still selling mojitos under Hemingway's signature.

Mid-range travel runs $110/day in Cartagena and $80 in Havana — but the Havana number lies. US travelers cannot use American credit or debit cards anywhere in Cuba, so you must bring all cash in euros or Canadian dollars and exchange on the ground, and the unofficial rate moves daily. Cartagena is straightforward financially and has reliable WiFi, ATMs, and Ubers. Havana takes more planning, more cash, and more patience, but rewards it with a city that genuinely doesn't feel like anywhere else on Earth. Cartagena wins on convenience and beach-day infrastructure; Havana wins on visual texture and the music — live son trios in every plaza after 7 PM.

Both share a December through March dry season — Cartagena's window stretches into March, Havana's runs through April. Pro tip for Havana: book paladars (private restaurants) ahead through your casa particular host, since the best ones (La Guarida, San Cristóbal) book a week out, and bring at least $100/day in euros cash you actually plan to spend. The 1-hour 30-minute flight between them runs $200-300 with one stop. Pick Cartagena for a polished colonial trip with Caribbean beach access. Pick Havana when you want a city that genuinely feels suspended in time.