10 Colonial Cities in the Caribbean: Where Fortaleza San Felipe Ranks

1. Cartagena de Indias, Colombia

The grand champion of colonial Caribbean cities. UNESCO walled city, pastel mansions, Castillo de San Felipe de Barajas. Direct flights from most US hubs.

2. Old San Juan, Puerto Rico

UNESCO-listed cobblestone city with twin star forts (El Morro and San Cristobal). Easy from the cruise port.

3. Santo Domingo, Dominican Republic

Oldest European-founded city in the Americas (1496). Zona Colonial UNESCO district with Fortaleza Ozama, the cathedral and the Alcazar de Colon.

4. Havana, Cuba

UNESCO Old Havana with Castillo de la Real Fuerza, the Morro and the Cabana. Hardest to access from North America logistically.

5. Puerto Plata, Dominican Republic

The North Coast colonial centre, anchored by Fortaleza San Felipe (1577) at the end of the Malecon. Smaller and quieter than Santo Domingo. Easy from cruise ports.

6. Trinidad, Cuba

UNESCO-listed colonial sugar town, beautifully preserved 18th century streets.

7. Camagüey, Cuba

UNESCO city with a unique twisted street plan designed to confuse pirates.

8. Willemstad, Curaçao

Dutch colonial with pastel facades on the waterfront. UNESCO listed.

9. St George's, Grenada

Pastoral horseshoe harbour with Fort George overlooking the bay.

10. Bridgetown, Barbados

UNESCO Historic Bridgetown and its garrison.

Frequently asked questions