January 24, 2025

How to Legally Travel to Cuba

For US travelers hoping to step back in time, savor vibrant culture, and explore some of the Caribbean’s most historic and beautiful towns, Cuba offers an experience unlike any other. While it is still necessary to navigate specific travel regulations to explore this fascinating island nation, it is entirely possible to make the trip run smoothly—and we make it even easier on our new journey, Cuba: A Cultural Odyssey. This guide covers all you need to know about traveling to Cuba legally and shares insight into some of the incredible places we visit on our adventure.

What are the current travel restrictions for Cuba?

The US-Cuba relationship has a complex history stretching back to the 1960s. In 2016, the United States marked a historic change by allowing US citizens to travel under the “people-to-people” category (license), lifting a decades-long limit that restricted virtually all travel to the island nation. But by the following year and under a new administration, the US reinstated new sanctions that prohibited Americans from using specific hotels, restaurants, and businesses that were owned, affiliated, or funded by the Cuban government. These sanctions remain today, so it’s not surprising that many are left wondering how to legally travel to Cuba. 

Here’s the good news: according to the US Department of the Treasury’s Office of Foreign Assets Control (OFAC) guidelines, US citizens can legally travel to Cuba if they fall under one of the 12 authorized categories or licenses, including visiting family, educational activities, religious activities, and humanitarian projects. The license that most travelers fall under, and the one we operate under for our cultural journey is the new “Support for the Cuban People” license. This is the most popular category, and it requires that travelers engage in activities supporting Cuba’s independent businesses, like dining at paladares (privately owned restaurants), staying in casas particulares (private homes), and engaging in cultural exchanges It’s worth noting that bringing back Cuban cigars and rum to the US are strictly prohibited under any category.

What do you need to do to legally travel to Cuba? 

One of the great things about traveling with Wilderness Travel is we provide a detailed itinerary that complies with the “Support for the Cuban People” category. We only stay at approved hotels that are not owned by the government (complying with all US and Cuban laws). To travel to Cuba, you’ll need:

  • A Cuban Tourist Card (Visa), which you can obtain online or through your airline after booking your flight. (The Cuban Consulate has extended the deadline for the use of paper visas until June 2025, after which time visas are exclusively available online).
  • Travel insurance that is valid in Cuba. Please note: only certain insurance companies cover travel to Cuba. We recommend using InsureMyTrip.com to compare which option is best for you.

For more information about travel requirements to Cuba for US citizens, we suggest visiting the Cuba Visa Services website FAQ page

Can I fly directly to Cuba from the United States?

Yes, there are daily flights to Havana and Santa Clara, Cuba from major US airport hubs, including Miami, Houston, New York, and more. As of January 20205, major US airlines that fly to Cuba include American, United, and Delta, just to name a few.

Top Places to Explore in Cuba

Cuba is an enticing blend of colorful colonial architecture, breathtaking landscapes, and a warm, welcoming culture. Its cities are filled with history, art, music, and traditional Cuban cuisine, making it one of the Caribbean’s most unique destinations. Here are our top three must-see destinations on your Cuban journey.

Havana

No visit to Cuba would be complete without experiencing the heart and soul of the nation. This lively capital is known for its iconic vintage cars, music-filled streets, and awe-inspiring architecture.

  • Walk the Malecón, the famous seafront promenade, where locals and tourists alike gather to enjoy ocean views, music, and dancing.
  • Explore La Habana Vieja (Old Havana), Havana’s UNESCO-listed historic district, where cobblestone streets and colonial buildings exude old-world charm. Famous picturesque landmarks include Plaza de la Catedral and El Capitolio.
  • Visit Plaza de la Revolución (Revolution Square), the center of Cuban history and politics, featuring the iconic Che Guevara mural and the towering José Martí Memorial.

Cienfuegos

Known as the “Pearl of the South,” Cienfuegos is a beautiful coastal city with French influences and stunning architecture, making it feel distinctly different from other Cuban cities.

  • Visit the 18th-century fortress of Castillo de Jagua (Jagua Castle), overlooking the bay with sweeping views of the coastline.
  • Stroll down Paseo del Prado, a wide boulevard lined with charming pastel buildings and a blend of French and Caribbean styles.
  • Visit Laguna Guanaroca, a fantastic place for birdwatching, including seeing the vibrant resident flamingos.

Trinidad

Trinidad is a UNESCO World Heritage site and a gem of Cuba’s colonial past, where you’ll feel transported back to the 1800s. This colorful town is surrounded by mountains and sugar plantations, making it ideal for travelers seeking history and nature.

  • Discover the lush forests, waterfalls, and hiking trails of Topes de Collantes National Park, home to Cuba’s diverse flora and fauna.
  • Explore Plaza Mayor in the heart of Trinidad, the main square surrounded by picturesque pastel-colored colonial buildings and churches.
  • Visit the stunning Valle de los Ingenios (Valley of the Sugar Mills), located just a short drive from Trinidad. This valley is home to the remnants of 19th-century sugar plantations and is a UNESCO site. You can also climb the Manaca Iznaga Tower for breathtaking views.