Editor's Note: Effective June 5, 2019, Americans are no longer permitted to travel to Cuba by cruise ship due to U.S. government policy changes.
Cruising around Cuba became a reality when a new cruise line, Cuba Cruise, launched Havana-to-Havana cruises in December 2013, and ran a second season from December 2014 through March 2015.
Cuba Cruise chartered Celestyal Cruises' 1,200-passenger Celestyal Crystal and rebranded it with some pretty bright flowers and a number of new restaurants. The ship makes quite an entrance when it pulls into ports that –- in some cases -– had never welcomed a cruise vessel.
The weeklong cruises begin in Havana (or Montego Bay, Jamaica, depending where you choose to board) and circumnavigate the island clockwise, stopping at Antilla, Santiago de Cuba (passing Guantanamo Bay on the way), Montego Bay, Cienfuegos/Trinidad and La Isla de Juventud.
The ship stays late in port in Havana (1 a.m.) and Santiago (9 p.m.), allowing passengers to get a real feel for these cities.
Cuba Cruise is unique in that it is the only line that circles the island, allowing you to discover places that would take days to reach by car because of the poor roads. It also offers fine shore excursions, which allow you to get to know both the culture and rhythms of this extraordinary island, as well as getting to know its inhabitants.
Havana's port is opposite the fortified battlements of Castillo de los Tres Reyes Magos del Morro, or Morro Castle, which dominates the skyline. The ship slips carefully between the city walls and the promontory as it enters and leaves. The port -- Terminal Sierra Maestra -- is in an ideal spot at the bottom of Havana Vieja -- the old part of town. Directly opposite lies Plaza San Francisco, with its imposing baroque church and adjoining monastery. You can walk to Calle Obispo, a pedestrianized street that cuts through the old town.
Tip: The street is hectic and touristy, but author Ernest Hemingway's two favorite bars sit at either end: La Floridita, for the best daiquiris in town, and Bodeguita del Medio, for the best mojitos. A few yards from here is Plaza de Armas, one of Havana's prettiest squares, lined with booksellers and cafes.
The Malecon in Havana
The Malecon is one of the most iconic sites of Havana. The beauty of arriving by ship (though you have to be up early), is that you can see the whole of the Malecon -- which stretches the length of the city -- gradually come into view.
At all times of day or night, you'll find locals strolling, fishing, chatting, drinking, kissing, flirting or simply hanging out. It is not lined with hundreds of bars and restaurants -- like many other spots in the Caribbean -- you'll find just a handful dotted along its entire length. Despite being a six-lane highway, there is hardly any traffic except at rush hour.
Tip: Walk along it, and you'll pass iconic sites at the bottom of the main thoroughfare: C/O'Reilly, the Nacional hotel and the old U.S. Embassy.
Plaza de la Revolucion
The much-photographed Plaza de la Revolucion is vast (one of the biggest squares in the world) and was the spot for many revolutionary speeches from Fidel Castro. A memorial to one of the revolutionary leaders, Jose Marti -- a 358-foot tower and 59-foot statue -- dominate the square. It's pretty soulless, consisting mainly of faceless Soviet-style government buildings and ministries, as well as the National Library and the Post Office, which is fascinating if you are into stamps.
Tip: There are a lot of photo ops here, but the main reason tourists visit -- apart from the revolutionary history -- is to get that iconic image of Che Guevera and the words: Hasta la Victoria Siempre -- "Until victory, always," on the side of the Interior Ministry building.
The iconic 1950s or in some case '40s American cars are very much a sight in Havana, and indeed the rest of the country. What is astonishing is that not only are they still running, but they look great, too. Cubans spend an enormous amount of time looking after their cars -- the bulk of it hunting for spare parts when the cars break down, which they do frequently.
Tip: In recent years, as President Raul Castro has loosened the state's grip on private enterprise, more and more of these cars -- Buicks, Chevys, Oldsmobiles and Fords -- have become taxis, rather than just private vehicles, earning their owners much-needed income. You can hail one in the street, or hire one for a city tour for 10 Cuban convertible pesos (CUC) (about $11) for an hour, which includes your ebullient guide. Inside, they are always hot, with cracked leather seats, stuck windows and handles that don't work, but they are as woven into the fabric of Havana as cigars and rum.
Celestyal Crystal's Riviera Pool
Celestyal Crystal is a lovely ship, and it's fun to have a sea day at the start of the cruise, but the ship is not what this cruise is about: It's about discovering Cuba.
However, when you are onboard, there's plenty of space to sunbathe on Deck 10 and on the Riviera Pool Deck, which includes the Riviera Bar. The pool is really not big enough if the ship is at its full 1,200-capacity and sun loungers, tables and chairs surround it.
Here, you'll find the sailaway parties and barbecue lunches on sea days, drinks promotions and vegetable carving demos. There is also a station promoting the specialty restaurant, drinks packages and spa deals. Above the pool deck is an open area for sunbathing, with deck chairs dotted about.
Tip: On Deck 11 is an observation area, perfect for when the ship is pulling into port and great photo ops.
Celestyal Crystal's Balcony Suite
Celestyal Crystal features 10 cabins with balconies -- two Imperial Suites, and four regular suites along either side of the ship. A corridor has a concealed sink and bar area behind a sliding wardrobe door, to the left. The living room includes a sofa and small table. Sliding glass doors lead into the bedroom, which has a double bed, side tables and plenty of wardrobe space.
Everything about these suites feels chunky and old school, comforting in its solidity. The bathroom is split into a toilet area (with a washbasin), a central area with another washbasin and shower cubicle. A door leads from the toilet into the corridor.
Tip: Balconies are tiny. If you want to sit out there, you have to ask for furniture that fits.
Before Celestyal Crystal pulled in, the tiny port of Antilla had never witnessed the arrival of a cruise ship. Although the ship is scheduled to call there later this year for the second season, the port is a notoriously difficult one for the captain to maneuver, with a clearance of just 3 meters between the hull and the seabed, and there's no chance the port will be dredged.
Tip: Antilla is a small, non-descript town that serves as the gateway to the northeast coast of Holguin. It's not worthwhile hanging around Antilla, so it’s best to take an organized shore excursion out of town.
Cuba Cruise offers a number of notable shore excursions, one of which includes a visit to the landing site of Christopher Columbus, followed by a tour of a small farm. Here you can stroll through a banana plantation, suck on sugarcane pulled from the ground and eat a sweet banana, before enjoying a local snack and a strong coffee.
Tip: The farmer keeps a Plymouth car from 1948 in his garage and assures us that he still drives it every day from his house to the market and back. Ask him whether he'll start it up for you; he might even let you sit in it.
Holguin is the name of a region in the top northeast of the island, which was developed for tourism in the 1960s, mainly for Soviet tourists when money from the U.S.S.R. propped up the island. It's evident in its architecture, which is all Soviet-era housing and hotel complexes, plonked indiscriminately on exquisite white-sand beaches. The Holguin shore excursion also includes a visit to Guardalavaca Beach, a beautiful stretch of white-sand beach flanked by two ugly all-inclusive hotels and a flea market.
Tip: The market sells all sorts of products, many handcrafted locally, such as sculptures, carvings, shells and clothes, and apart from souvenir shops in Havana (which mainly sell T-shirts and caps), this is the best place to pick up authentic souvenirs.
Santiago is Cuba's second-largest city, at the far eastern tip of the island, and the cruise's second stop. It has a population of around 1.2 million and much more of a Caribbean feel than Havana. Santiago is noisy, bustling and polluted, an onslaught to the senses after the countryside we saw in Antilla.
There is no advertising of any sort. There are some discreet "Se Vende" (for sale) signs, now that selling your house has become legal, and the only graffiti is "Viva Fidel" or the revolution in general.
Tip: To get away from the craziness, head to the town's most famous hotel, Hotel Casa Granda, where 3 "pesos convertibles" gets you great views and a drink at its rooftop bar, which overlooks the bay.
Plaza Dolores in Santiago
Don't miss Plaza Dolores, where old men play speed dominoes. The square is crammed with bars and people -- locals and tourists alike -- sipping the local beer, Cristal, and watching the world go by.
Tip: Whether you like it or not, you will encounter a degree of hassle if you sit here. The best thing to do is say a polite no, and the musician/hawker will move on. After a while, they will get the idea that you just wish to be left in peace. The best place to watch the world go by is La Perla del Dragon, where a beer will set you back 1.50 CUC.
Cienfuegos is in the center of the south coast of Cuba. The ship usually stops here after a day in Montego Bay, Jamaica, where the vessel pulls in to refuel and restock -- neither fuel nor the quality of food passengers expect onboard are available in Cuba. But the Montego Bay visit is a shock to the system after being in Cuba for four days, with Wi-Fi, wall-to-wall advertising and Diet Coke, all freely available.
Cienfuegos is the most impoverished of the places the ship goes: Think big, empty, dusty, potholed streets; horse and carts the primary means of transport; kids playing with tin cans in the street in lieu of a soccer ball. It's grinding and sometimes hard to take in. And yet -- as with everywhere else in Cuba -- you have pockets of beauty, like an old man who was playing guitar in the street. He wasn't doing it for tips; he was just sitting outside his house, strumming away.
Tip: When going to Cuba it's always worth bringing along a number of items we take for granted. For kids, it's pens, pencils, school notebooks, erasers etc., and it's quite acceptable to hand these out. For adults, it's cosmetics, especially soap, razors and shampoo. All of these are accepted with great gratitude, and it's a lot less demeaning than handing out money.
La Isla de Juventud, Cuba
La Isla de Juventud (Isle of Youth) is the final stop before the ship returns to Havana. Lying just 60 miles off the south coast of Cuba, the island is a picture-postcard perfect island: powder sand beaches, pristine reefs, crystal clear water -- and no tourists (except us). The ship moors just offshore and passengers take a tender to the jetty (pictured here), at the beach at Punta Frances, which is on the far south of the island.
Tip: At this stop, it's all about the beach and sun loungers. You need to purchase drink tickets to partake at the pop-up bars. It's a stop that goes quickly, as the ship needs to leave at 2:30 p.m. to get to Havana early the next morning. (Cuba Cruise is looking to extend the hours in upcoming seasons.)