Santiago de Cuba — Castillo del Morro

Santiago de Cuba sits at the southeastern tip of the island, spread across a wide bay that opens directly to the Caribbean between two flanking mountain ranges — the Sierra Maestra to the north and the Sierra de la Gran Piedra to the south — a setting so dramatic that arriving by sea the city feels like it has been scooped out of the mountainside and deposited at the water's edge.

The Castillo del Morro, a massive 17th-century Spanish fortification, stands on the eastern point of the bay entrance, its 21-metre-high walls, corner towers and gun platforms built to control the narrow channel through which all shipping into Santiago de Cuba had to pass. The fort was designed by the Italian military engineer Giovanni Battista Antonelli and built in sections between 1633 and 1700, and it remains the most complete and impressive example of Spanish colonial military architecture in the Caribbean.

The city itself is the most Afro-Cuban in character of all Cuba's major cities — the music is louder, the streets feel more alive, and the cultural continuity with West Africa is more immediately present in the language, religion, music and food than in Havana. The casas de cambio on the side streets blare Cuban son and reggaeton from dawn, and at night there are spontaneous street parties and processions that can break out without warning.

The annual Carnival in February is the largest in Cuba, with enormous floats, traditional comparsas dance troupes and all-night street processions that fill the main avenue for the entire week leading up to Ash Wednesday. The surrounding Sierra Maestra, Cuba's highest mountain range, rises directly behind the city and was the base for Fidel Castro's guerrilla campaign in the 1950s; the Pico Turquino peak (1,974 m) is reachable by a demanding multi-day trek from the mountain villages above the city.

The San Juan Hill battlefield, where Theodore Roosevelt's Rough Riders fought the Spanish in 1898 during the Spanish-American War, lies in the hills above the city and is accessible by a rough road that climbs through coffee-growing countryside to a small monument and a viewpoint over the valley. The battle is a contested moment in Cuban history — a struggle that Cubans fought and died in, only to have the United States occupy the island shortly after. The annual carnival's finale features the burning of the cascarella, a symbolic figure representing the year's bad luck, set alight on the main avenue in a tradition that draws participants from across the city.

The Castillo del Morro (San Pedro de la Roca) was inscribed on the UNESCO World Heritage List in 1997 as the most complete example of Spanish colonial military architecture in the Caribbean.

Santiago de Cuba is the centre of Afro-Cuban cultural life and hosts the largest Carnival celebration in Cuba each February.

The city provides direct access to the Sierra Maestra mountain range and the historical sites of the Cuban revolutionary guerrilla campaign.