Cuba’s “off-limits” feel has long made it a perpetually popular destination for intrepid travelers. Globe Aware offers one-week volunteer vacations that allow our volunteers to explore and enjoy Cuba without the stress of planning once they land.

I Travel to Cuba All The Time — For U.S. Travelers, It’s Much Easier Than You Think

December 14, 2023
By Associated Press
By Carley Rojas Avila

The desire to travel to Cuba is a classic case of wanting what you think you can’t have. Cuba’s “off-limits” feel has long made it a perpetually popular destination for intrepid travelers.

Cuba has been named TripAdvisor’s number-one trending destination worldwide and is one of the top 10 most desirable tropical destinations for American travelers.

As an American citizen married to a Cuban, I’ve traveled to Cuba numerous times and know that travel to Cuba is far from off-limits. In fact, it’s easier to travel from the United States to Cuba than it has been in decades. U.S. travelers don’t even need family on the island or rigid group travel plans to do it. Your long-awaited vacation to Cuba might be closer than you think.

Ever-Shifting Cuba Policy

When the Obama administration announced significant changes to the long-held, Cold War-era U.S.-Cuba policy at the end of 2014, the island instantly became the biggest news in travel. Interest in traveling to Cuba soared from travelers in the United States and beyond. Just two years after the Obama administration’s big announcement, tourism on the island just 90 miles off the coast of Key West rose 56% over pre-2014 levels.

With the Trump administration’s professed desire to undo all of President Obama’s policy changes towards Cuba, travel to the island seemed to once again be in jeopardy for American travelers. However, Trump-era regulations did little to roll back the new ease with which American travelers could visit the island.

What the restrictions enacted by the Trump administration accomplished quite successfully was convincing Americans that Cuba was again “off-limits” for travel. It isn’t. In reality, Cuba remains almost as easy to visit as it was since Obama’s monumental policy changes — and more accessible than it has been for decades and decades.

How to Travel to Cuba Legally

How are U.S. citizens traveling to Cuba these days? Long gone are the days of needing special permission from the U.S. government to travel to Cuba. Now, there are several reasons Americans can travel to Cuba without requiring permission from the U.S. government to do so.

One of those reasons is to “Support the Cuban People.” Planning a trip where you’ll stay at a locally-owned boutique hotel or guest house, tour the city with a local guide, shop in boutiques, and eat in Havana’s buzziest restaurants? Your trip will be one that will support Cuban small business owners and, therefore, easily qualify as a trip designed to help the Cuban people.

There’s no need to register your trip ahead of time, travel with an organized group, or apply for a visa. Simply book your airline ticket and accommodations before going to Cuba — it’s that easy.

Keep in mind as you make your bookings that some websites may ask for your reason for traveling to Cuba, or indicate there are restrictions for U.S. travelers in Cuba. Should you encounter this, stating that you’re traveling to Cuba to “support the Cuban people” is more than sufficient.

Worried about safety in Cuba as an American traveler? Don’t be. After spending significant chunks of time in Cuba over the past decade, I’ve never felt even slightly unsafe as an American. In fact, after traveling to 40+ countries, I can confidently say that Cuba is one of the countries where I’ve felt the safest.

Planning Your Trip

Remember that the irregular state of U.S.-Cuba regulations makes some aspects of Cuba slightly more confusing, though not necessarily more challenging if travelers know how to prepare for the experience.

Trump-era regulations mean that hotels and resorts on the island partially or entirely owned by the Cuban government are off-limits for U.S. travelers. Planning around this restriction is easy, and a comprehensive list of hotels and resorts to avoid is available online. Instead, there are plenty of stunning locally-owned boutique hotels and guesthouses, ranging from affordable rooms for rent to sprawling 19th-century mansions, that are restriction-free.

Navigating issues of cash and currency in Cuba can be more of a challenge. For decades, the U.S. government has enforced strict limits on U.S.-based businesses operating in Cuba, meaning that debit cards and credit cards linking to banks and credit unions based in the United States will not work in Cuba.

For American travelers planning to visit the island, you’ll need to come prepared with cash in hand — all the cash you’ll need for the duration of your trip. Online booking sites for accommodations and popular activities like tours in vintage cars and rum tastings make it increasingly easy to avoid swiping your plastic while in Cuba. However, planning your travel before touching down in Havana is a crucial step in the experience.

While traveling with cash in hand can make it challenging for more extended stays in Cuba, for the average traveler, it’s a small price to pay to finally be able to cross Cuba off the bucket list.