Rooftops by the Cuban sea

Why the Best Time to Travel to Cuba is Now

Rooftops by the Cuban sea

Cuba sits just 90 miles south of the Florida coast. Our Caribbean island neighbor has played an outsized role in our nation’s history and culture. Yet Cuba still remains a mystery to the vast majority of Americans.

For over 50 years the island had been off-limits to U.S. citizens before President Barack Obama thawed diplomatic relations with Cuba. But with a new administration taking over in Washington, here’s a look at why the best time to travel to Cuba is right now:
Streets of Cuba
Get There Before Cuba Changes

Over the past few years the Cuban government has relaxed its restrictions on tourism. The United States has likewise made it easier to get to Cuba–although pure tourism is still not an authorized reason for Americans to travel to Cuba. These changes have opened the island to both visitors and investors.

For Cubans in need of income and professional opportunities, the influx of travel revenue is a huge benefit. Cuba is in desperate need of foreign money to improve the infrastructure and quality of life on the island. But tourism– especially mass tourism– comes at a cost. Tourism can force cultures to change to meet the needs of visitors. This will change the Cuban people and the visitor experience. Right now, Cuba is utterly devoid of ritzy hotels, suffocating beach crowds, and Western food franchises.

“There are several reasons why now is the best time to travel to Cuba,” says April Springer, Custom Travel Planner for International Expeditions’ tours of Cuba. “But the one that sticks out is the one we hear all the time– going before Cuba changes. Some people get offended by that statement, so let me clarify: I mean before the beautiful Habana Vieja is overrun with cruise ship passengers. Before the corner café puts up the Starbucks sign. Before the historic buildings are purchased by Marriott. Cuba has changed significantly over the last three years, so I can only imagine what will happen in the next three.”
April Springer in Cuba
Get There Before the Crowds

As Springer points out, Cuba is no stranger to visitors. After the collapse of the Soviet Union in the early 1990s, the Cuban government opened the floodgates to tourists in hopes of injecting some much-needed cash into the economy. But in the last three years, since the thawing of U.S.-Cuba relations, the number of tourists has skyrocketed.

“In 2015, Cuba welcomed more than 3.5 million tourists,” Springer points out. “But only a small percentage of those were American travelers. That’s a lot of travelers for an island nation with a population of around 12 million people. I don’t know that specifically the Americans will change Cuba. But the sheer numbers of travelers are already proving difficult for the Cubans to handle. Good hotels are scarce. Cuba is importing more goods than ever before. And while the flights may not be bringing as many tourists as projected, the cruise ships are coming in hot.”

Looking across Bay of Havana
Cuban Heritage

Of course, going to Cuba is not just about beating the crowds. There are a number of other reasons why now is the best time to travel to Cuba. Cuba has an incredible amount to offer travelers.

With nine UNESCO World Heritage Sites, Cuba is a treasure trove of fascinating architecture and culturally important locations. Consider Old Havana and its fortification system, which dates back to the 16th-19th centuries, when Havana was one of the most important port cities in the Western Hemisphere. You can see that history in its mix of architectural styles, which range from Baroque to Neoclassical.

Then there is the San Pedro de la Roca fortress, located just outside Santiago de Cuba. A massive, well-preserved structure, the fort dominates the narrow straight that allows access to the city on the eastern tip of Cuba. In short, Cuba has a vast wealth of historical sites that are worthy of any visitor’s time.
Cuban artist
Cuba’s Rich Culture

Cuba has a thriving art, music, and dance scene. The music is everywhere– in the plazas, in the courtyards, in the bars, in the clubs, and on the street corners. I felt like my time in Cuba always had its own sweet soundtrack. Cubans love their music, and it is stunning to realize just how many people there can play it.

The visual arts are likewise hard to avoid. There are murals along nearly every street, and small artists’ studios abound. Americans in general are fairly ignorant when it comes to Cuban art, but Cuba’s painters, sculptors, and writers are respected all around the world for their creativity.

Of course, part of this is due to Cuba’s relative isolation from Western culture. As the floodgates of travel open wider, you can expect Cuba’s cities to become increasingly globalized.
Cuban children
The Cuban People

I’ve been to nearly 50 countries over the past 30 years, and I’ve never been to any place that was more welcoming to visitors than Cuba. As great as the country’s history and culture are, it’s the people of Cuba that really made my visits to the island priceless. I have made many lifelong friends there.

Cubans have an authentic approach to hospitality that’s deeply rooted in their traditional culture. The island is a melting pot of people from every point on the planet. I don’t mean to be Pollyanna-ish about it, but in my mind Cuba stands out for its working multiculturalism.

Cubans are also genuinely excited that Americans are finally returning. Since Cuba hasn’t been crushed with an overwhelming influx of tourism yet, having visitors is still special for them. So you can expect to make some great new friends on your trip to Cuba.
Classic car ride
How Will the Trump Administration Change Relations with Cuba?

It is hard to know what the Trump Administration will do regarding American travel to Cuba. All of the changes that President Obama made to improve relations with Cuba were done by executive order. This means that President Trump can easily reverse those moves with his own executive orders.

Trump has stated numerous times that he feels the changes is U.S.-Cuba relations made under Obama only benefit the Castro regime. In a tweet he sent just after the death of Cuba leader Fidel Castro, Trump warned of the possibility of cutting ties. As bad as the impending rush of American travelers to Cuba may be, Trump reversing Obama’s warming of relations between the countries would be worse. It’s just one more reason why now is the best time to travel to Cuba.

“I try not to worry with Cuba,” says April Springer. “I try to think like my Cuban partners do: Anything is possible, and nothing is guaranteed. International Expeditions is ready to respond to any changes the US government may make to the current Cuba policies. IE was one of the first companies to apply for, and be granted, People-to-People licenses from the OFAC office. No matter the outcome, IE is prepared for tightening of policy, and we are ready with our partners in Cuba if things should continue to open up.”

How to Travel to Cuba Now

International Expeditions offers three Cuba travel options by land and sea, including our Complete Cuba tour, small-ship Cuba cruise and private travel crafted to meet your interests.


Jim O’Donnell is a freelance environmental journalist and conservation photographer. He is the author of “Notes for the Aurora Society: 1500 Miles on Foot Across Finland.” In addition to his blog, Around the World in Eighty Years, his writing and photography have appeared in National Geographic Maps, New Mexico Magazine, Perceptive Travel, and more.