Cuba feels like nowhere else on earth.
For one, there's no advertising. You'll also find no U.S. products, no Starbucks, no McDonald's, no Coca-Cola. There may still be food rationing and horse-drawn carts and 60-year-old Chevys, Buicks and Fords used for transport, yet the island also boasts some of the best medical and educational facilities in the world. The highest income per month (for a doctor) is pegged at $28, and the average is half that.
School kids are immaculately dressed and extremely polite. There is no commercial TV, radio or magazines. And private enterprise exists only on an extremely limited scale. But there is no trash in the streets and crime is rare.
Stuck in a time warp since the Cuban Revolution in the late 1950s, and under strict embargo by the U.S. since, a visit to the island transports you to another era. If you are a U.S. citizen, your cellphone won't work, and your dollar won't go as far as you might expect. The U.S. dollar is pegged to the tourist currency, the CUC, or Cuban convertible peso, and the official exchange bureaus charge a 10 percent fee (which does not happen with any other currency).
You will also notice that this is nothing like any other Caribbean island: You will not be assaulted by hawkers from Colombian Emeralds shops and franchises selling Tanzanite. There are no Senor Frogs or Pirana Joes in the ports, and there is no scrum of people and passengers as you get off your ship. Apart from the odd day in Havana, yours will be the only cruise ship visiting a port.
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Despite dire warnings of how awful Cuba's food can be, it has markedly improved since President Raul Castro took over for his brother Fidel Castro in 2008. Previously, all restaurants were state-run, and the food was notoriously bad. The ongoing process of reform included allowing licenses for privately run eateries. Paladars, as they are known, are springing up everywhere, especially in Havana, and offer a far more pleasant dining experience, both in terms of cuisine and service, than state-run restaurants. Raul Castro has also permitted the ownership of cellphones and for Cubans to buy and sell property, which under Fidel Castro was not permitted (houses were simply passed on from generation to generation).
The Cuban people are warm, inquisitive and generally unexposed to popular culture. Bear in mind that most of the population has never left the island, has lived under the same government their entire lives, has only watched state-run TV, read state-run newspapers and listened to state-run radio. There is no available Internet, except for tourists in big hotels, no Twitter, no Facebook, no celebrity culture -- nothing that we take for granted when we travel in most of the rest of the world.
This may sound romantic. But spend time talking to locals, and you'll soon learn that the poverty and lack of socioeconomic mobility is a great source of frustration for Cubans. Any form of dissent or union activity is strictly banned, and although not a "harsh" regime like that in North Korea or Iran, people are still imprisoned for political reasons. Cubans yearn to see the rest of the world: Witness the almost weekly rescues by cruise ships of those trying to make land in the U.S.
But Cuba is changing -- perhaps not as fast as residents would like -- and for that reason alone, now is the time to go. Cruising around the island is the ideal way to see it -- out of the way ports, a chance to see the whole island in a week (impossible by car) and the opportunity to really get a feel for its culture and rhythms.
Best Time for Cuba Cruises
All the above-mentioned cruises offer itineraries from December to March; there are no cruise lines operating outside of these months. The weather is typical for the Caribbean, with temperatures around 80 degrees (28 Celsius). Expect an occasional mid-afternoon shower.
Cuba Cruise Lines
Cuba has long been under embargo from the U.S. Although it has become much easier to visit Cuba, thanks to a thawing of relations in the Obama Administration, individual U.S. citizen still need to go through some red tape to go.
People to people" organizations will provide American cruisers with the paperwork that allows them to go, and several companies are taking advantage of this. Other cruise lines have decided to offer educational or humanitarian programming that allows them to sail under current U.S. guidelines.
Since 2013, Celestyal launched the first around-the-island itinerary, and has continued to offer regular cruises on Celestyal Crystal. You can book a Havana-to-Havana round trip, or opt for a Montego Bay-to-Montego Bay roundtrip.
In a first from a mainstream cruise company, Fathom -- Carnival Corp.'s "social impact" line -- began cruising to Cuba in May 2016; it has approval to do so from both the U.S. and Cuban governments. Other cruise lines that have permission to sail to Cuba include the French-owned Ponant, which will begin offering voyages from Miami in 2017; International Expeditions, which sails on Variety Cruises' Panorama within Cuba under people to people guidelines; and Lindblad-National Geographic Expeditions, which is also using a Variety Cruises' ship, Panorama II, for Cuban itineraries, beginning in 2016.
American consumers should know that several cruise lines are selling Cuban itineraries before they have the required permissions. These include Viking Oceans, Grand Circle, Victory Cruises and Pearl Seas. All companies expect to have those permits before the cruises take place, although Pearl Seas was forced to cancel a series of sailings in early 2016 because approvals didn't come in time.
For international passengers, MSC Cruises has MSC Opera homeported in Havana. MSC Armonia will join her from November 2016. Fred. Olsen, Thomson Cruises and Noble Caledonia, also stop in Havana as part of longer Caribbean cruises. As of fall 2016, the first commercial flight service to Cuba from the U.S. began, although these are still limited. For non-Americans, regular flights to Havana and Varadero on both scheduled and charter carriers are available from Mexico, Canada and the U.K., as well as other European countries.
Cuba Cruise Itineraries
If you want to get a real feel for the island, you need to go beyond Havana (which is a bit like New York is to the U.S. or London to the U.K.). Cuba Cruise, International Expeditions, fathom and Noble Caledonia Cruise plan to make multiple stops in Cuba and give you a real chance to get to know the country. The other lines make an overnight port stop in Havana, which is a wonderful city and totally different from any other place you'll visit in the Caribbean. It's enough for a taste of Cuba, which will no doubt leaving you wanting more.
Cuba Cruise with Havana Port Stop: Thomson Cruises, which attracts a predominantly U.K. passengers, will call at Havana once this year (in December 2014), and five times next year, as part of its Cuban Fusion cruise, roundtrip from Montego Bay, where it is home ported for the 2014-15 season. Thomson Dream overnights in Havana, giving passengers a real chance to get to know this amazing city.
Fred. Olsen Cruise Lines, which also attracts predominantly U.K. clientele, will also overnight in Havana on its ship Braemar. When MSC Opera homeports in Havana in late 2015, the ship will be in the city for two nights.
Full or Partial Cuba Circumnavigation: In 2014 and 2015, Cuba Cruise was the only line to offer a full circumnavigation of the island. In 2016, the ship will still stop at multiple ports, but passengers will no longer sail the entire breadth of the island. International Expeditions and fathom make several stops on the island when their cruises. Noble Caledonia offers one semi-circumnavigation of the island, on the 107-passenger MS Serenissima. The ship hits five Cuban ports and a couple additional Caribbean islands.
Cuba Cruise Port Highlights
Havana, Cuba. Havana is so wrapped up in history and romance that the moment you arrive you find yourself swept up in its charms. The heart of the city is Habana Vieja, or Old Havana, which fans out from the huge Revolution Square, where cobbled streets, 50s cars and crumbling houses are exactly as you imagined. The trick is not to spend too much time around these touristy areas. Instead, head toward some of the neighborhoods like upscale Vedado, or some of the less-visited squares and parks. Or simply take a stroll along the seafront Malecon. It is worth visiting a cigar factory and a rum factory while you are there, but if you are lucky enough to visit in the evening, you should wander at will, as Havana becomes a different city at night, with music spilling from every other doorway, live bands and nightclubs open till dawn.
Santiago de Cuba. If you thought Havana was hectic, you ain't seen nothin' yet. Santiago, on the far eastern tip of Cuba, is a crazy, intense, noisy, polluted but exhilarating city, which has more of a Caribbean feel than anywhere else you are likely to visit on the island. Spread atop a steep hill, it's the second-largest city in Cuba, with a population of 1.2 million. If you are interested in the history of the revolution, this is the cradle of it, and monuments to martyrs and revolutionary leaders dot the landscape.
Trinidad, Cuba. This town is so ridiculously beautiful it has been given UNESCO World Heritage status. It's a tiny town, with cobbled streets and squares, and pastel-colored houses with wrought iron balconies. Every other doorway is a Casa de la Musica (a simple bar where musicians come and play), and there is a wonderful Caribbean vibe to it, with pristine beaches nearby and lazy palm trees in the square. If you stay here till the evening, visit the La Cueva disco, built into a cave above the Plaza Mayor.
Cienfuegos, Cuba. Dusty, flat and poor, Cienfuegos is not the most inspiring place in terms of atmosphere, but it makes up for this with its architecture. This town also has UNESCO World Heritage status, for its city center, which has the largest number of neo-Classical buildings in the Caribbean. Just outside is the Jardin Botanico Nacional. Founded by Edwin Atkins in 1901 and sponsored by Harvard University, it ranks as one of the world's most important tropical gardens. Over an area of 90 hectares, it is home to more than 2,000 species of plants from five continents.
La Isla de Juventud, Cuba. If you are looking for a picture-perfect Caribbean paradise, then look no further. This place is genuinely untouched. Punta Frances, on the far south of the island, just consists of a long white sand beach, clear warm waters and very little else. There is a tiny "museum" that gives a short history of the island, two pop-up bars and an old man selling carvings from a small stall. What you won't find -- unlike many other stops in the Caribbean -- is people coming up to you trying to sell trinkets/drugs/souvenirs/anything else. It's truly hassle-free.
Holguin, Cuba. This town is not the prettiest of places, but nearby you can visit Cayo Barjay, where Christopher Columbus first made landfall. You also can stop at Guardalavaca beach, which features an all-inclusive resort and a slightly tacky flea market, but is a pretty beach, nonetheless. This area was first developed for tourism back in the 1960s, when Cuba welcomed Russians from the former Soviet Union, and many Soviet-era apartment blocks and the two main hotels, were built to cater to the influx.
Cuba Cruise Tips
Take stuff to give away. Schoolchildren in particular are desperate for pens, notebooks, pencils, erasers, pencil sharpeners and felt tips. Younger kids love candies (of course), but take a couple of bags and hand some out (it's so much better than handing out money). Adults are grateful (particularly women), for any cosmetics: razors, face creams, shampoo, soap, etc.
Take items you can't live without. You are allowed to take your favorite soda, coffee, chips, cookies or other snacks into Cuba. So, if you can't live without it, pack a suitcase full.
Be patient. As in the rest of the Caribbean, the pace is slower in Cuba. Sometimes things stop for a reason: a spare part can't be found, there's no one to man the ticket desk or the office is closed.
Explore. Cuba is one of the safest places on earth, and the people are some of the friendliest you are likely to meet. Go off the beaten track, spend time in non-tourist cafes, hang out in squares watching the old men play dominoes -- it's all part of the culture and the rhythm of this extraordinary island.
Bring cash. Outside of Havana, ATMs are not to be found. Canadian dollars, British pounds and euros are all accepted. Change your money at the airport where the lines are shorter than in the banks in town. U.S.-registered credit cards (American Express, Visa and Mastercard) are not accepted.
Don't be naive. However lovely the Cubans are, money is an absolute driver, and a tourist equals cash. So, when someone approaches you to offer you a restaurant/taxi/girl/guy, be aware that they want a cut. Don't be afraid to say a firm "No." Unlike some countries with aggressive touts, most Cubans will take no for an answer and soon disappear. Drugs are not typically present in Cuba, but there is widespread prostitution, so if someone approaches you in a bar and is over-friendly, they are probably after your cash rather than a chat.