Cuba Travel Guide

After decades of political strife, Cuba and her humans draw from the mysticism of uncertainty and live to embrace the present moment. Wearing heart and history on their sleeve- the streets, the cars, the style, the people are truly a unique work of revolutionary art.

Despite what many U.S. citizens are made to believe, it is legal - and fairly easy - to travel to Cuba, and 2020 is shaping up to be a wonderful year to make a visit to the crocodile island, nicknamed for its reptilian shape. Throughout the last decade the Cuban government has made it more accessible for citizens to own and run businesses. This allows for both the Cuban people’s benefit and more services being made available to visitors at a better price!

Even more recently, in the last several years, there has been a massive surge then drop-off in tourism; thus, allowing locals the money and time to refurbish their homes and businesses. With improved establishments and far less tourists crowding the streets, now is without doubt a brilliant time to travel to Cuba.

Here, I hope to offer a quick glance into Cuba’s history, a look at current relations with the United States, and a few tips and tricks for a successful journey.


Many things about the way Cuba’s system is structured might not seem to make sense - even to the locals - which is why it is helpful to have a loose understanding of the island’s history when trying to understand the current framework of regulations. Indigenous genocide, slavery, two wars for independence, corruption, and revolution have all been major events that have molded the history of this little country next to giants.


  • 1000 BCE - Arrival of Cuba’s first indigenous people, the Guanahatabey, from South America

  • 1200 CE - Taino people arrive and grow maze, tobacco, cotton, and Yucca

  • 1492 - Second stop by Christopher Columbus on Turtle Island, claims for Spain

  • 1511 - Diego Velazquez establishes Baracoa, first Spanish settlement, and begins conquest of Cuba for Spain; large portion of the native Taino population is killed over the next several years by disease and force

  • 1526 - Colonialism picks up speed, and African slaves are brought to work tobacco and sugar

  • 1607 - Havana named capital

  • 1868 - 1st War of Independence with Spain

  • 1886 - Slavery abolished in Cuba

  • 1895 - 2nd War of Independence led by Jose Marti and Maximo Gomez

  • 1898 - U.S. helps Cuba defeat Spain at battle of San Juan Hill, giving Cuba independence from Spain

  • 1901 - Cuba’s new constitution includes the Platt Amendment which restricts Cuba’s independence, giving the U.S. the right to oversee interfere in Cuban affairs

  • 1902 - Tomás Estrada Palma elected Cuba’s first President. Guantánamo Bay leased to the U.S. as part of the Platt Amendment

  • 1906 - Rebellion led by Jose Gomez; United States intervenes

  • 1940 - Batista elected president under Communist Party