How to Vacation to Cuba

Update: As of June 6, 2019, cruises to Cuba are no longer available due to travel restrictions imposed by the United States. However, you can still visit Cuba with one of our land tour operators! To learn about alternative cruise vacations, including land tours, please call 1-800-377-9383.

Cuba’s rhythm is irresistible with a colorful blend of culture, music, and tropical beauty that makes it one of the Caribbean’s most fascinating destinations. Whether you arrive by cruise ship or join a guided land tour, this island nation welcomes you with warmth, charm, and timeless allure. 

Why Visit Cuba on a Cruise 

Exploring Cuba by cruise offers a seamless way to experience the island’s highlights while enjoying all the comforts of your ship. From Havana’s vintage cars and lively plazas to Santiago de Cuba’s vibrant music scene, each port reveals a new side of Cuban life.  

Cruises to Cuba often include stops in Havana, Cienfuegos, and Santiago de Cuba, where you can enjoy curated shore excursions like salsa dance classes, historical walking tours, and visits to local markets. With no need to repack or plan every transfer, a cruise makes discovering Cuba easy and unforgettable. 

Top Cruise Ports in Cuba 

Havana is the heart of Cuba, a city full of colonial architecture, cobblestone streets, and soulful melodies drifting from every café. Wander through Old Havana, a UNESCO World Heritage Site, where pastel buildings and classic cars create the perfect backdrop for your Caribbean adventure. 

In Cienfuegos, you’ll find elegant French-inspired architecture and access to the nearby colonial town of Trinidad, another UNESCO gem.  

Farther east, Santiago de Cuba boasts a rich Afro-Cuban heritage, rhythmic energy, and panoramic views from Castillo del Morro.  

Each port tells its own story, blending history, art, and the joyful pulse of Cuban life. 

Experiencing Cuba Beyond the Cruise 

For those who want to linger longer, a handful of licensed land tours offer immersive cultural experiences across Cuba. These guided programs often include extended stays in Havana, scenic drives through Viñales Valley, visits to tobacco farms, and performances by local musicians. 

Travelers enjoy authentic encounters with Cuban culture while traveling under approved cultural exchange programs. These tours provide a deeper connection to Cuba’s people and traditions. 

What to Expect on a Cuba Vacation 

A trip to Cuba is as much about feeling as seeing. You’ll be swept up in the rhythm of street musicians, the aroma of fresh-roasted coffee, and the sight of oceanfront promenades lined with classic cars. Expect a warm welcome everywhere you go.  

Cubans are proud to share their art, stories, and hospitality. From salsa dancing in the evening to dining at a family-run “paladar,” Cuba’s experiences are rich and rewarding. Traveling with trusted cruise lines or licensed tour companies ensures your trip is both seamless and meaningful. 

Exciting Activities on a Cuba Vacation 

• Step back in time with an architectural tour of Havana, a city that appears straight out of the 1950s. Visit the expansive Revolution Square and stroll along cobble-stoned streets lined with vintage cars.  
• Spend a day at one of Cuba’s picturesque white sand beaches. Right away, you’ll notice that the beaches in Cuba are much less crowded but no less beautiful than those found in the more visited Caribbean islands.  
• Tour an authentic Cuban cigar factory and learn about the country’s fabled cigar history. You’ll leave with a huge appreciation for the craft after seeing all the work that goes into one of Cuba’s famous hand-rolled cigars.  
• Visit the National Museum of Fine Arts to view a vast collection of Cuban art spanning multiple styles and time periods. This will help paint a broader picture of Cuba as a whole, and you’ll enjoy a break from the Cuban heat!  
• Walk along the fortified walls of the Morro Castle, a former Spanish military complex that now features museum exhibits and one of the finest views of downtown Havana.  

Planning Your Cuban Vacation 

Ready to experience the magic of Cuba? The Cruise Web’s travel experts can help you find the best Cuba cruises and land tour packages, guiding you through every detail.  

From choosing the right itinerary to selecting culturally enriching excursions. Our team can match you with the perfect Cuba vacation, whether you prefer a quick getaway or an in-depth journey through the island. 

Timeless Cuba Awaits 

Cuba remains one of the Caribbean’s most captivating destinations, where history, culture, and natural beauty blend effortlessly. Whether you’re sailing into Havana’s harbor or strolling through the countryside on a guided tour, every moment reveals another reason to fall in love with this extraordinary island.  

Let The Cruise Web help you discover Cuba, your gateway to an unforgettable Caribbean experience.