As Cuba's third oldest city, dating back more than 500-years, Trinidad is rich in history and culture. For those intrigued by Cuba's colonial past outside of Havana, look no further than the cobblestone streets and picturesque plazas of Trinidad. Between the 16th and 18th centuries, the Spanish settled here in between the Caribbean Sea and the Sierra del Escambray mountains. They mined for gold and ran vast sugar plantations with slaves from neighboring Jamaica, bringing enormous wealth to the area. The fame and fortune may not have lasted, but Trinidad's lofty mansions and grand cathedrals have stood the test of time. The city now holds UNESCO World Heritage status and strict preservation laws to protect its historic center. Touristy Trinidad is certainly no secret but, despite the crowds, it is hard not to fall for its charms. With men on horseback roaming the palm-shaded alleyways, it's still easy to imagine a quieter time.

For an insight into Cuba's colonial past, the revolution and its unique cultural makeup, head all the way down to the southeast of the island. Almost as far from Havana as you can be without jumping over to Jamaica, you'll find Santiago de Cuba, one of the country's most historic and intriguing cities. In its 500-year lifetime, Santiago has witnessed the rise and fall of Spanish rule, and with it the abhorrent slave trade. It has become the home of Cuba's largest Afro-Caribbean population and a unique blend of religions. In 1953, it is where Fidel Castro launched his revolution with the first armed attack. Santiago de Cuba has extensive museums and elegantly preserved forts, cathedrals, and homes that help to tell the story of Cuba's past. Visit the final resting place of national hero Jose Marti, and the army barracks of Moncada and you'll start to understand how Cuba came to be where it is today.

In a country known for its old-world charm, there is nowhere quite as historic as Old Havana. Wander the cobblestone streets where countless others have before you and your mind will easily tread its own imaginary path into the past. Baroque, neoclassical, and art nouveau architecture are living evidence of the city's 500-year history and colonial past. Now protected by UNESCO status, these beautiful buildings stand resplendent in sunny plazas throughout the city where locals congregate for a stroll and a catch-up. Visit the former Governor's Palace, which now houses the Havana City Museum, or explore the old forts that once protected the city's harbor for the Spanish. The Museum of the Revolution is not to be missed, and the Cristóbal Colon Cemetry can introduce you to some of Cuba's most famous historical figures. Every corner of Cuba's capital is ready to tell a story if you take the time to look and listen.