Cruising to Cuba – What You Need to Know

After decades of an embargo on all things coming out of Cuba and heavy restrictions on tourism, U.S. citizens have been making the trip to the island country just about 100 miles to the south of Key West since 2016. Several airlines are now featuring flights to Havana and it is no longer illegal to bring home goods from the island. In addition to air travel, several cruise lines are now hosting itineraries with ports like Havana, Cienfuegos, and Santiago de Cuba on the list of stops along the way.

If a cruise to Cuba is on your short list of absolute must-do vacations, then we’re here to help you with all the information you’ll need before booking accommodations. A solo trip to Cuba is possible right now, but requires a great deal more planning and will ultimately be more costly. We highly recommend one of the many cruise options being offered by top-notch lines like Carnival, Royal Caribbean, Norwegian and even higher-end lines like Azamara, Oceania, and Regent Seven Seas.

Best Time to Book A Cruise to Cuba

Currently, cruises to Cuba are taking place throughout the year, but we recommend traveling in the December-March time frame, when the weather is less humid. Cuba is in the Caribbean and Summer and Fall can be quite hot and stifling. The Summer and Fall months also present a much greater possibility for hurricane weather affecting the islands and hurricanes and vacations don’t go well together.

Itineraries and What to Do

Currently, there are seven major cruise lines along with several smaller lines making sailings to Cuba. Departure ports include Fort Lauderdale, Miami, Tampa/St. Petersburg, Port Canaveral, and Boston. Most cruise lines will bring passengers to a long day or overnight stay in Cuba’s most iconic city, Havana. By all accounts, Havana is romantic, charming, and so rich with history, you’ll feel like you’ve stepped back in time. It’s also unlike any other city in Cuba and the Caribbean for that matter, so to get a true taste for the country, you’ll want to visit some of the other featured towns and cities. In no particular order, here is a list of cities or towns that could fall on your cruise to Cuba itinerary and what to do while you’re there:


Havana gets a lot of the glory when people think and talk about the allure of Cuba and rightfully so. From Old Havana (Habana Vieja) and its cobble stone streets to the long esplanade and seawall called Malecón to the outdated and often crumbling mansions in the Vedado neighborhood, Havana is a city rich with culture, sights, sounds, smells, and generally friendly people. If visiting on a cruise, an overnight stay in Havana is ideal as the city becomes a different place at night with live music in the streets, dancing, nightclubs, and all manner of entertainment. There are plenty of activities to take part in during the day as well, so don’t fret if your itinerary only has you there for a long day. Here are some examples of daytime excursions you may want to consider:

  1. Visit one of Hemingway’s favorite spots, El Floridita for the “best daiquiri in the world,” according to the writer.
  2. Take a classic car tour through the old streets of Havana.
  3. Do a Cuban cigar factory tour and see how the world-renowned stogies are made.
  4. Do a rum factory tour and see what makes all those daiquiris so tasty.
  5. Visit the Morro Cabańa, a fort built in the late 1800s to protect the island nation from invaders.
  6. Make a trip to Santa Maria Beach and relax.
  7. Take the HavanaTur bus tour to visit the memorials and learn about the Revolucion leaders like Che Guevara.
  8. Visit the Fabrica de Arte art gallery.

Santiago de Cuba

On the opposite end of the island from Havana and closer to Haiti and the Dominican Republic lies the second-largest city of the island nation, Santiago de Cuba. It’s a frenetic, lively city steeped in rich cultural tradition and is a great place to explore for some historical context of the country. Known as the birthplace of the Cuban revolution sparked by Fidel Castro in the 1950s, the city has no shortage of museums and monuments to educate citizens and visitors on the guerilla rebellion that shaped the country into what it is today. Also known as the birthplace of rum and salsa, you’ll find plenty of opportunities for lightheartedness in the city a well. Here are some examples of things to do while visiting Santiago de Cuba:

  1. Walk around Parque Céspedes, a bright and inviting public square in the heart of the city.
  2. Walk around the waterfront district of El Tivolí and admire the bright and colorful buildings as you make your way through the winding streets.
  3. Visit the Parque Zoológico where the entire family can see wild and exotic animals from the region.
  4. If traveling at the end of July, you’ll be able to enjoy Carnivals, with floats, parades, dancing, and overall partying in the streets. Takes place July 21-28.
  5. Catch a baseball game at the Estadio Guillermón Moncada, the best stadium on the island.
  6. Visit the 17th Century UNESCO World Heritage Site known as the Castillo de San Pedro de la Roca, a military fortress built to defend the port.
  7. Go dancing at the legendary Casa de la Trova, which hosts live music every night and is a quintessential Cuban experience for music lovers.


Located on the Southern coast of Cuba and facing the Bay of Cienfuegos, this gem of a city is not as lively as Havana or Santiago de Cuba, but should  still be a must on your itinerary. Founded by the French in 1819, the city features beautiful French colonial architecture and as one of the country’s newest settlements, has a completely different look and feel than the rest of the country. Here are some great things to do while visiting Cienfuegos:

  1. Do a tour of the Laguna Guanaroca with a short forest walk and an opportunity to see pink flamingos.
  2. Walk around the urban center of the city and admire the beautiful French colonial architecture.
  3. If you have an overnight in Cienfuegos, it could be worth the trip to visit the El Nicho Waterfalls about an hour and a half from the city.
  4. Go to the Punta Gorda and visit the Palacio de Valle and have a drink on the rooftop bar. You won’t be disappointed.
  5. Visit the Castillo de Jagua, a fortress accessible by ferry just off the coast of Cienfuegos.
  6. Spend an hour or an entire day in the Jardin Botanico Nacional, a botanical garden sponsored by Harvard University with more than 2,00 species of plants from five continents.

Other notable places to keep an eye out on cruise itineraries are Trinidad, Holguin, and La Isla de Juventud. Trinidad is a small well-preserved town with lots of charm. Holguin is a city in the eastern part of the country with a wonderful park in its city center and a great history museum. La Isla de Juventud is a gorgeous island directly to the south of Havana with several resorts and great beaches.

If you are thinking of booking a cruise to Cuba sometime soon, feel free to contact a travel concierge or submit a travel request to learn more about your options.