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Cruising has become the easiest way to visit Cuba — and with most major cruise lines offering itineraries to the enigmatic Caribbean island, there are more options than ever for exploring its history and culture, no matter what your budget. Peak sailing season for Cuba is December to early March, and there’s still time to book a cruise to  Havana, and perhaps two or three of the island’s other vibrant cities. Read on to discover which of the best Cuba cruises in early 2019 is right for you.

Affordable Havana & Key West Combo

These two legendary cities, separated by just 106 miles of water, make for a fun and relaxing 4- or 5-night itinerary — and some ships call on the Bahamas, too.

4- or 5-Night Cuba Cruise on Norwegian Sky: Havana’s pre-revolution nightlife was legendary. An overnight there — combined with the open-bar policy aboard the 2,004-passenger Norwegian Sky — make these Cuba cruises, which depart Miami on Fridays (Jan. 11, Feb. 8 and 22, and March 22 and 31), a fun and affordable option for those seeking fun. The ship also calls on Key West (and Great Stirrup Cay, Norwegian’s private island in the Bahamas), and fares start at $599 per person. Note: If Orlando is more convenient, Norwegian also has 4-night itineraries to Cuba from Port Canaveral on the just-refurbished 1,936-passenger Norwegian Sun starting in April.

4- or 5-Night Cuba Cruise on Royal Caribbean’s Majesty of the Seas: Onboard the recently refurbished, 2,350-passenger Majesty of the Seas, you’ll cruise roundtrip from Fort Lauderdale (Jan. 14 and 28; Feb. 12; and March 11 and 25 departures) and call on Key West before heading to Cuba for an overnight in Havana. Fares start at $610 per person. If you prefer to visit Nassau, Bahamas, the ship does a 4-night Cuba itinerary (Jan. 10 and 24, and March 7 and 21 departures), starting at $459 per person.

5-night Cuba Cruise on Carnival Paradise: Cruise this 5-night itinerary from Tampa — departing on March 2 and 30 and April 13 — aboard the 2,124-passenger Carnival Paradise , which was refurbished in 2018, and you’ll enjoy a daytime visit to Key West followed by a full day and overnight in Havana and two Fun Days at Sea. Carnival’s ships are known for their lively poolside ambience, nightlife, and affordability — fares start at $559 per person.

In-depth Cuba Itineraries

To experience three or four Cuban cities and embrace the island’s unique arts and culture, consider a longer itinerary with an onboard educational element.

7-Night Cultural Cuba Cruise on Viking Star: If you’re seeking a sophisticated ambience, expert-led lectures on Cuban history, and cultural experiences on shore, you can enjoy all three on this 7-night Cultural Cuba itinerary from Miami onboard the 930-passenger Viking Star.  Viking offers this itinerary weekly in January and February, with fares starting at $2,799 per person. You’ll call on Cienfuegos (where you can take an overnight excursion to Havana for historic touring and an evening at the famed Tropicana nightclub) and Santiago de Cuba, a baroque city known as the Cradle of the Cuban Revolution. Two sea days offer time for relaxation and additional insight from onboard experts.

9-Night Cuba Intensive Cruise on Azamara Journey: For a deep dive into Cuban history and culture, this 9-night Cuba Intensive itinerary aboard the 690-passenger Azamara Journey,  refurbished in 2016, is about as comprehensive as it gets. Departing Miami on Jan. 15 and 24, and Feb. 2, 11, and 20, this cruise visits Havana for a full day and evening (with a 2:00 a.m. departure), Cienfuegos, and Santiago de Cuba (overnight with an AzaMazing Evening of Cuban Rhythms at the Heredia Theatre), and calls on Key West. Fares start at $3,249 per person.

7-Night Colonial Cuba Cruise on Oceania Sirena: The 7-night Colonial Cuba cruise from Miami on the 684-passenger Oceania Sirena , which joined the fleet in 2016 after a multi-million-dollar refurbishment, departs Jan. 13 and calls on Havana (with a late departure so passengers can sample the city’s famous nightlife), Cienfuegos, and Santiago de Cuba, plus two relaxing sea days. Fares start at $2,199 per person.

Cuba & Caribbean Island Itineraries

If you love visiting a variety of islands in the Caribbean, why not make Cuba an exciting new port of call? You can on these multi-island cruises.

10-Night Authentic Cuba Cruise on Holland America’s Veendam: This Cuba and Western Caribbean sailing on the 1,350-passenger Veendam departs Fort Lauderdale on Jan. 4 and visits Havana (overnight) and Cienfuegos on Cuba; as well as Cozumel, Mexico; Belize City, Belize; and Georgetown, Grand Cayman. Fares start at $1,759 per person. If you like to plan further out, a 7-night Authentic Cuba itinerary, leaving Oct. 23 from Fort Lauderdale, also on Veendam , calls on Havana and Cienfuegos as well as Georgetown, Grand Cayman, and Ocho Rios, Jamaica, priced from $1,199 per person.

7-night Caribbean, Cuba and Antilles Cruise on MSC Armonia: This sailing on the 2,679-passenger MSC Armonia , which was refurbished in 2014, is an affordable option that departs Miami weekly from Jan. 7 to March 18 and offers an overnight in Havana along with calls on Montego Bay, Jamaica; Georgetown, Grand Cayman; and Cozumel, Mexico. Cruise fares start at just $499 per person, so there’s value here if your main goal is to cruise the Caribbean and experience the highlights of Havana.

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