The 10 Best Cuba Cruises

Here are 10 of the very best Cuba cruise options, covering all styles and sizes, durations (from quick hits to full-on immersion), and budgets—so hop on board, the mojitos and cigars are just a sailing away.

The 10 Best Cuba Cruises

Norwegian’s four- and five-night Cuba-bound voyages out of Florida bundle in a full open-bar on each sailing.

Courtesy of Norwegian Cruise Line

[Editor’s Note: Due to Trump administration-imposed travel restrictions to Cuba as of June 2019, cruise ships have been effectively banned from bringing American travelers to the island nation. The Associated Press reports that would-be cruisers who have already booked their trips prior to the policy change will still be permitted to travel, though details on the process remain murky; check in with individual operators for the latest updates.]

There’s perhaps no sweeter travel proposition than taking that proverbial bite out of once-forbidden fruit . . . and juicy Cuba, with its vibrant culture, lively locals, rich history, and transporting tropical setting, is ripe for the picking. However, despite it being the largest of the Caribbean islands—situated a mere 90 miles from the United States—the destination can feel frustratingly out of reach, thanks to the logistical hoop-jumping required of American travelers, even with thawed U.S.-Cuba relations in recent years.

Happily, cruising makes a Cuba vacation a breeze, seamlessly bundling lodging, transport, and excursions and managing all of the required red tape for guests, because the trips are aligned with current U.S. government travel requirements (for travelers, that means going on preapproved cultural/educational exchanges, via a “people-to-people” visa).

Indeed, cruise lines have seized upon this convergence of eased regulations and pent-up traveler demand to service Cuba, with available itinerary options skyrocketing in recent years. Their recipe has had resonance: Cruising lets you get around the large island in ease, from a comfortable home base, with plentiful excursion options while offering relative affordability compared to land-based vacations.

Of course, this ain’t your typical sun-and-surf Caribbean cruise (although it’s got plenty of that, too). Maybe you’ve got your heart set on history-rich Havana (it turns 500 years old in 2019), with its time-warp 1950s classic cars, crumbling colonial buildings, and storied night spots (such as the Tropicana or Buena Vista Social Club). Or perhaps you want to see the country’s second-largest city and Cuban Revolution–cradle at Santiago de Cuba or visit Cienfuegos, with its UNESCO-protected city center. Whatever your interests, there’s a cruise to match.

Upscale cruise line SeaDream started sailing to Cuba in 2019, with immersive itineraries on voyages between Havana and Cienfuegos.

Upscale cruise line SeaDream started sailing to Cuba in 2019, with immersive itineraries on voyages between Havana and Cienfuegos.

Courtesy of SeaDream

Plush mega-yacht line SeaDream kicked off its Cuban presence in early 2019, with a portfolio of eight “Cuba Collection” voyages aboard its 112-passenger SeaDream II; the line offers an additional eight sailings to Cuba in 2020, aboard its 112-guest SeaDream I. The seven- to nine-night immersive itineraries sail between Havana and Cienfuegos (and vice versa) with an exclusive focus on Cuban ports along the island’s western coastline, including some lesser-visited locales like Trinidad, Cayo Largo, Isla de Juventud, and María la Gorda. Excursion highlights include a night out at a Cuban cabaret in Havana (with transfers via a classic car) or a snorkeling trip on the pristine coral reefs of Bahía de Corrientes. Sailings from January through March 2020; rates from $4,599/person;

Virgin Voyages
The most buzzed-about new cruise line on the horizon is Richard Branson–brainchild Virgin Voyages, carving out an industry niche with its stylish, adults-only, party-hearty cruise model. When the line debuts its first ship, the 2,770-passenger Scarlet Lady, in April 2020, its maiden voyage will feature an overnight stop in Havana. The ship goes on to host a season of four- and five-night Cuban voyages from Miami, all inclusive of an overnight call in Cuba’s capital, as well as a stop in Bimini in the Bahamas. Excursion and onboard programming details are forthcoming, but the ship is a welcomed retreat with sweet features like 20-plus dining options, ocean-facing cabanas, a vinyl shop, and the first tattoo studio at sea. Sailings from April through October 2020; rates from $1,500/person;

Oceania Cruises
Luxe Oceania runs a robust range of Cuba-inclusive itineraries, including a slate of convenient seven- to 11-night voyages round-trip out of Miami, aboard the recently revamped 684-passenger Insignia or Sirena. Itineraries vary slightly, but typically include overnights in Havana, as well as calls in Cienfuegos and Santiago de Cuba (a few of the longer itineraries feature rare-for-the-industry overnight stays in those two cities, too, for fuller immersion). Choose from excursions like an arts tour of colonial Cienfuegos or a farm-to-fork culinary outing in Havana. Sailings in July 2019 and from September 2019 through March 2020; rates from $1,499/person;

Seabourn Cruise Line
Swank Seabourn is making way for an inaugural season in Cuba in late 2019. Book one of five 11- to 25-night sailings running round-trip out of Miami (or between Miami and San Juan, Puerto Rico) aboard the 458-passenger Seabourn Sojourn (featuring a Thomas Keller–backed dining venue on board). Itineraries differ but include overnight stays in Havana, Cienfuegos, and occasionally Santiago de Cuba, as well as calls in Isla de la Juventud and/or Antilla, along with other Caribbean stops sprinkled in (such as the Cayman Islands, Jamaica, or the Dominican Republic). Sailings in November and December 2019; rates from $4,999/person;

Havana turns 500 years old in 2019, and visiting is a step back in time, complete with ubiquitous 1950s classic cars.

Havana turns 500 years old in 2019, and visiting is a step back in time, complete with ubiquitous 1950s classic cars.

Courtesy of Viking

Viking’s ocean arm runs weeklong winter cruises to Cuba round-trip out of Miami. Sail the 930-guest, all-veranda Viking Sky on immersive itineraries that include four full days docked in Cuba via an extended three-day port call in Cienfuegos; excursions from that city can be arranged for a tour of colonial Trinidad or an overnight hotel-based excursion to Havana. The ship also includes a one-day stop in Santiago de Cuba. Back on board, luxuriate in one of two pools (including an infinity pool at the ship’s stern) or at the Scandinavian-inspired LivNordic Spa. Sailings in January, February, and November 2020; rates from $2,599/person;

[Editor’s Note: Following the engine failure of the Viking Sky in Norway in March 2019, a Viking spokesperson assured AFAR of the following:“The safety and well-being of our guests and our crew is always our first priority. An initial independent investigation into the incident identified a potential oil lubrication issue, as a result of this we have adjusted our policies and procedures to ensure that this issue could not be repeated.”]

Norwegian Cruise Line
Norwegian offers carefree, quick-hit voyages to Cuba out of Miami (on the 2,004-passenger Norwegian Sky) and Port Canaveral (aboard the 1,936-guest Norwegian Sun), with four- and five-night trips that bundle in a full open-bar on each sailing (yes, mojitos are included!). Choose from itineraries that pair an overnight stay in Havana with stops in Key West or Norwegian’s private Bahamian island at Great Stirrup Cay. Shore excursions include tours of Havana in classic American cars, performances at venues like the Tropicana or Buena Vista Social Club, or art outings to hip contemporary arts venue Fábrica de Arte Cubano. Upgrade a sailing on either of the recently renovated ships with a suite-level stay for extra perks like priority embarkation/disembarkation, free Wi-Fi, and specialty dining passes. Year-round sailings; rates from $249/person;

Silversea Cruises
Newly launched in early 2019, the small ships of all-inclusive, butler-serviced Silversea now sail to Cuba, with a series of winter voyages running round-trip out of Fort Lauderdale. Choose from some dozen sailings in 2020 aboard the recently refurbished, 298-passenger Silver Wind. Voyage details vary but may include an overnight in Havana and a call in Santiago de Cuba (sometimes overnighting there), or (more rarely) Cienfuegos, plus visits to spots like Key West or Bimini. Choose from 34 shore excursions: Take in jazz at a Havana club or visit Cojímar, the seaside village that inspired Hemingway’s The Old Man and the Sea. Sailings from January through March 2020; from $3,330/person;

Variety Cruises
Greece-based Variety Cruises (in partnership with “people-to-people” Cuba program specialists Beyond Cruises) offers fall and winter sailings aboard its 49-guest three-masted sailing ship Panorama. On seven-night routes between Cienfuegos and Havana (or in reverse), itineraries incorporate less-trafficked Cuban locales like Trinidad, María la Gorda, and Isla de la Juventud. On-the-ground small-group excursions emphasize cultural immersion via encounters with local artists and artisans: Meet with musicians behind the Buena Vista Social Club or with an artisan in a woodcarving studio in Trinidad, for instance. Sailings in November 2019, January 2020, and February 2020; rates from $2,717/person;

Carnival has more than 100 Cuba sailings scheduled through 2020, embarking from seven different U.S. cities.

Carnival has more than 100 Cuba sailings scheduled through 2020, embarking from seven different U.S. cities.

Courtesy of Carnival Cruise Line

Carnival Cruise Line
Carnival—best known more for its splashy, mass-market “fun ships”—is notable in the Cuban market for sheer numbers: The line has over 100 Cuba sailings scheduled through 2020, running from more U.S. homeports than any other cruise line, including Miami, Fort Lauderdale, Port Canaveral, and Tampa, with soon-to-launch options out of Charleston, New York, and Norfolk. The range of three- to nine-night itineraries incorporate either full-day or overnight calls in Havana, coupled with stops in other Caribbean-region ports like Cozumel, Key West, and Nassau. On board the five 2,052- to 3,006-passenger ships servicing the region (Carnival Sunshine will be the largest ship to call on Havana when it starts the first-ever Cuba cruises from Charleston in November 2019), guests can expect Cuban-themed music, deck parties, lectures, and salsa dance lessons, too. Year-round sailings; rates from $309/person;

Pearl Seas Cruises
Pearl Seas Cruises offers 11-night Cuba cruises that sail round-trip from Fort Lauderdale aboard the 210-passenger Pearl Mist. The itinerary incorporates overnight calls in Havana and Santiago de Cuba, as well as in Cienfuegos, Trinidad, and the more rarely visited seaport town of Casilda, taking in all the requisite outings en route (cruising Havana in a classic car, trailing Hemingway, listening to steel drums). Sailings from October through December 2019; rates from $5,335/person;

>> Next: Everything Americans Need to Know Before Traveling to Cuba

Elissa Garay, modern-day explorer, perpetual seeker, and diligent travel scribe, has traveled to and reported on nearly 60 countries around the globe.
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