DESTINATION

Cuba

Step into a world of vintage charm, vibrant rhythms, and living history—from the pastel-painted facades of Old Havana to the lush tobacco valleys of Viñales and the sun-kissed shores of Varadero. Cuba is a cruise destination that awakens every sense.

Discover Cuba by Cruise Ship

There’s nowhere quite like Cuba. It’s a place where time moves to a different beat—where 1950s convertibles glide past centuries-old cathedrals, where salsa rhythms drift from every open doorway, and where the aroma of freshly brewed Cuban coffee lingers on every corner. With UNESCO World Heritage Sites, a legendary music scene, world-renowned cigars, and some of the warmest people you’ll ever meet, Cuba delivers the kind of immersive experience that stays with you long after you’ve returned home. Whether your heart is drawn to history, culture, cuisine, or the sheer beauty of the island, a Cuba cruise promises memories you’ll treasure for a lifetime.

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Infectious Rhythms & Dance

Cuba is the birthplace of son, salsa, rumba, and mambo. You’ll hear live music pouring from open windows, plazas, and rooftop bars at every turn.

Centuries of Architecture

Stroll past Spanish colonial masterpieces, Art Deco treasures, and baroque cathedrals—many preserved as UNESCO World Heritage Sites—that tell Cuba’s remarkable story.

Flavors & Famous Cocktails

Taste slow-roasted ropa vieja, farm-fresh ceviche, and smoky black beans, then raise a glass with the island’s iconic mojitos and daiquiris.

Cuba’s Must-Visit Cruise Ports

Each of Cuba’s cruise ports opens a different chapter of the island’s culture, history, and natural splendor. Our expert advisors will help you select an itinerary that takes you to the places that matter most to you.

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Havana

Top Sights: Old Havana (UNESCO), the Malecón, El Capitolio, Plaza de la Catedral, Hemingway’s favourite haunts

Known For: Classic car rides, electrifying nightlife, hand-rolled cigars, colonial grandeur, live salsa around every corner

Perfect For: History enthusiasts, culture seekers, and anyone craving the full Cuban experience

Port Time: Full day or overnight

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Santiago de Cuba

Top Sights: San Pedro de la Roca Castle (UNESCO), Céspedes Park, Moncada Barracks, Bacardí Rum Museum

Known For: Afro-Cuban heritage, carnival traditions, the cradle of son music, revolutionary landmarks

Perfect For: Music lovers, history buffs, and travellers who enjoy off-the-beaten-path discoveries

Port Time: Full day

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Cienfuegos

Top Sights: Palacio de Valle, Tomás Terry Theatre, Punta Gorda neighbourhood, Jardín Botánico, nearby Trinidad

Known For: French-influenced elegance, the “Pearl of the South,” neoclassical beauty, stunning bay panoramas

Perfect For: Architecture admirers, couples, and those seeking a more tranquil side of Cuba

Port Time: Full day (with optional Trinidad day trip)

Cuba Cruise Ports at a Glance

Feature Havana Santiago de Cuba Cienfuegos
Atmosphere Energetic capital brimming with nightlife and street art Soulful city steeped in Afro-Cuban tradition Serene, refined, and French-influenced
Top Attractions Old Havana, Malecón, El Capitolio, cigar workshops Moncada Barracks, San Pedro Castle, carnival Palacio de Valle, Punta Gorda, day trip to Trinidad
Best For First-time visitors, history enthusiasts, nightlife seekers Music fans, history buffs, adventurous explorers Architecture lovers, couples, relaxed discovery
Time Needed Full day or overnight Full day Full day (with Trinidad excursion option)
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Let our team of expert advisors take the guesswork out of planning your Cuba cruise.

Cuba is a destination that rewards those who plan well. You can wander the cobblestoned plazas of Old Havana, cruise the Malecón in a cherry-red 1957 Chevy, sip a daiquiri at El Floridita where Hemingway once sat, explore a family-run tobacco farm in Pinar del Río, meander through the perfectly preserved colonial streets of Trinidad, unwind on the powder-white sands of Varadero, soak in the revolutionary spirit of Santiago de Cuba, and admire the refined French architecture of Cienfuegos. Many Cuba itineraries pair beautifully with stops in Jamaica, the Cayman Islands, or Mexico for the ultimate Caribbean combination.

If sorting through travel requirements, choosing the right itinerary, and finding the best rate feels like a lot, that’s exactly why we’re here. Our team of 23+ expert advisors—many of whom have sailed to Cuba themselves—will handle every detail. We’ll even monitor your fare weekly after you book to make sure you’re always getting the best possible rate. No fees, no hassle, just personal service from people who truly know cruising. Talk to a cruise expert today!

Pair Cuba with Other Caribbean Gems

A number of Cuba cruise itineraries weave in additional Caribbean ports, so you can experience Cuba’s one-of-a-kind culture alongside classic island escapes.

  • Jamaica – Reggae rhythms, Blue Mountain coffee, and the cascading Dunn’s River Falls
  • Cayman Islands – World-class diving, Stingray City encounters, and legendary Seven Mile Beach
  • Mexico (Cozumel) – Ancient Mayan ruins, vibrant reefs, and authentic coastal cuisine
  • Key West – America’s laid-back tropical outpost, just 90 miles from Cuba’s coast
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Find your specialty cruise today!

We’ll help find the perfect specialty cruise—whether you’re crossing oceans, transiting canals, or exploring the ends of the Earth.

When to Plan Your Cuba Cruise

Cuba’s tropical climate means warm weather year-round, but each season brings its own personality to the island.

Dry Season (November – April): Expect comfortable temperatures between 70–80°F, low humidity, and sunny skies—perfect for walking tours through Havana and open-air excursions. This is the busiest period, so we recommend booking well ahead to lock in the best cabin selection.

Shoulder Months (May – June, October): The weather remains pleasant with occasional showers, crowds thin out noticeably, and cruise fares tend to be more favourable. It’s a sweet spot for travellers who prefer a more relaxed, authentic experience.

Summer & Early Fall (July – September): Temperatures climb and humidity rises, with the occasional tropical rain shower. Cruise lines keep a close eye on weather patterns and reroute when needed. You’ll find some of the most attractive rates during this window.

Pro tip from our advisors: time your sailing around Cuban festivals for an unforgettable bonus. The Havana Jazz Festival in January and Santiago de Cuba’s legendary Carnival in July add a layer of excitement you won’t find anywhere else. Ask us about building your trip around these events.

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Why Book with Cruise Help

Expert Advisors

Specialty cruise specialists who understand the unique requirements of expedition and world voyages.

Exclusive Perks

Access to special deals, onboard credits, and amenities not available when booking direct.

Personalised Planning

Custom recommendations for ships, itineraries, and cabin selection on complex voyages.

Full Support

Assistance from booking through disembarkation and beyond—we’re with you every step.

Your Cuba Cruise Questions, Answered

Travel from the U.S. to Cuba is governed by the Office of Foreign Assets Control (OFAC). Americans can visit under specific authorized categories, and “Support for the Cuban People” is the one most commonly used by cruise passengers. In practice, this means participating in shore excursions that involve meaningful engagement with local Cubans—something most cruise line excursion programmes are specifically designed to satisfy. Because regulations can shift, our advisors stay current on every requirement so you can book with complete peace of mind.

You’ll need a valid passport with at least six months of validity remaining beyond your travel dates, plus a Cuban Tourist Card (visa) that your cruise line typically provides. U.S. travellers must also declare an authorized travel category and keep a record of their Cuba-related activities for five years after the trip. Cuban travel insurance is mandatory as well. It sounds like a lot of paperwork, but our team walks you through every single step—we’ve helped countless clients navigate these requirements smoothly.

Access to Cuba by cruise has fluctuated as U.S. regulations evolve. Lines that have operated or currently operate Cuba itineraries include Norwegian Cruise Line, Royal Caribbean, MSC Cruises, Oceania Cruises, Regent Seven Seas, Azamara, and a selection of smaller luxury and expedition brands. Because availability changes frequently, we always recommend checking with one of our advisors for the latest confirmed sailings and departure dates.

November through April—Cuba’s dry season—delivers the most comfortable weather, with daytime highs in the upper 70s to low 80s°F and low humidity. It’s also peak demand, so booking early helps secure the best cabin choices. If you’d prefer fewer crowds and better fares, the shoulder months of May–June and October offer a wonderful balance. Our team can help you weigh weather, pricing, and festival calendars to find the timing that suits you best.

Cuba itineraries range from short 4–5-night sailings with a single port call—usually Havana—to more immersive 7–14-night voyages visiting multiple Cuban ports plus other Caribbean islands. Some itineraries include an overnight in Havana, which gives you precious extra hours to explore after the day-trippers have left. Your advisor can match the itinerary length to your schedule and the experiences that matter most to you.

Cuba’s excursions are refreshingly different from the typical Caribbean beach-and-snorkel offerings. You’ll find guided walking tours through Old Havana, classic car city tours, cigar factory and rum distillery visits, Afro-Cuban music and dance workshops, farm-to-table cooking classes, local art studio visits, and day trips to the Viñales Valley tobacco country. Many of these are thoughtfully designed to satisfy the “Support for the Cuban People” travel category. Our advisors can recommend the excursions that will make your visit truly memorable.

In most cases, no. U.S.-issued credit and debit cards are generally not accepted in Cuba, so plan to carry enough cash for your time ashore. You can exchange dollars for Cuban pesos (CUP) at official CADECA exchange offices, though U.S. dollars may carry an additional surcharge. Euros and Canadian dollars sometimes get more favourable exchange rates. Your advisor can help you estimate how much cash you’ll need based on your planned excursions and shopping.

Cuba is widely regarded as one of the safest destinations in the Caribbean for visitors. Violent crime targeting tourists is exceptionally rare, and Cubans are known for their genuine warmth and hospitality. Standard travel precautions still apply—keep valuables secure, stay aware of your surroundings, and use organised excursions for added convenience and security. Cruise line shore programmes provide a well-structured way to explore with confidence.

Cuba’s most sought-after keepsakes include hand-rolled cigars, aged rum, aromatic Cuban coffee, and vibrant original artwork. U.S. travellers may bring back Cuban goods purchased for personal use—including cigars and rum—without a set dollar limit. Other popular finds include handcrafted leather goods, vintage-style posters, hand-painted ceramics, and musical instruments. Our advisors love sharing their personal favourite shopping spots from their own Cuban travels.

Many Cuba sailings weave in additional ports such as Jamaica, the Cayman Islands, Cozumel or Costa Maya in Mexico, Key West, and Honduras. This combination lets you experience Cuba’s singular culture alongside the Caribbean’s signature beaches and adventure activities. Ask your Cruise Help advisor about the latest combination itineraries—we’ll find the route that gives you the most rewarding voyage possible.