Cruises to Cuba: the Best Shore Diversions and Activities in Havana

With the old town just a stroll from the port, Havana’s historical legacy is an easy win for cruisers. From the 16th to 18th centuries, every buccaneer, privateer and scallywag pitched up in Havana looking to grab a piece of precious metal and any sugar or tobacco they could lay hands on. Cuba’s capital, founded on the island’s north coast in 1519 by the conquering Spaniards, was a way station and careening stop for their treasure fleets, which hauled plundered gold and silver from Latin America to Seville.

So destructive were the raids on Havana that the Spaniards raised castles on either side of the harbour.

As the pillaging increased, so did the size of the forts. Cruise ships sail out of Old Havana’s castle-bound harbour, one of the most commanding seaports in the world. Make sure you’re on deck for the full fortress experience on your right and the old town, castles and serpentine sea wall on your left. Ships either turn east along Cuba’s Atlantic coast, passing the colossal forts and eastern beaches of Havana, or west past the Malecón, the seafront promenade backed by its famous urban backdrop of crumbling classical, art deco and art-nouveau buildings.

The current revival of the harbour, on the eastern edge of the old town, is creating a more vibrant portside atmosphere as abandoned warehouses are resurrected. A new European-style beer hall — Almacén de la Madera — has opened next to the Almacénes de San José, a vast souvenir market. Other harbour attractions include a number of churches, the Havana Club rum museum and the muscular 16th-century fort Castillo de la Real Fuerza, which houses a shipwreck and treasure museum.

Old town

The harbour area won’t keep you long. It’s the enticing historic Old Havana (La Habana Vieja), a Unesco World Heritage site, which has the city’s prettiest buildings.

Located just behind the port road, close to the Sierra Maestra cruise terminal, it offers enough to engross visitors for days: Cuban baroque churches, cobblestoned plazas and colonnaded mansions with half-moon windows, as well as museums, restaurants, cafés and bars — all shaded by sprays of bougainvillea.

On its western side the straight streets of the old town empty onto the Prado promenade, a 15-minute walk from the cruise terminal. Alternatively, hire a bicycle taxi to navigate the narrow streets. Old Havana’s newest attractions include Factoría Habana (308 Calle O’Reilly, between Habana and Aguiar), a former paper factory turned contemporary art space, and Teatro de Títeres El Arca (Avenida del Puerto and Obrapía), the puppet museum and theatre that delights children at 3pm on weekends.

At the western end of Old Havana, don’t miss the Cuban art collection at the Museo Nacional de Bellas Artes (Trocadero, between Zulueta and Monserrate) and the glorious art-deco Bacardi Building (261 Avenida de Bélgica).Take a break for an ice-cool daiquiri at the scarlet bar in El Floridita (Calle Obispo), one of Ernest Hemingway’s haunts.

Lunchtime hot spots

Avoid Old Havana’s state-run tourist restaurants — with the exception of the acclaimed El Templete (Avenida del Puerto, corner of Narciso López) which has a tempting seafood menu — in favour of privately run paladares. Try buzzy tapas bar El Chanchullero (Teniente Rey 457A bajos, Plaza del Cristo), and the grilled meat and seafood selection at the alfresco La Terraza, inside Centro Asturiano (Prado 309, corner of Virtudes).

Latin beat

Music spills out of bars, dance halls, theatres and yards, offering a chance to catch a performance day or night. It’s notoriously difficult to find out what’s on but Cuba Absolutely’s monthly What’s On ( is a must, as are the music listings at Venture out of Old Havana, though, for authentic moves and tunes. Look out for the city’s latest hot ticket: musician X Alfonso’s one-of-a-kind Fábrica de Arte Cubano has just opened for art, music and entertainment in an old peanut-oil factory (Calle 26 between 11 and 13, Vedado).

Barrio hopping

Head west from Old Havana to explore the modern city, either by taking a tour in an American classic car or using the hop-on hop-off Habana Bus Tour. Inhale the salty air along the Malecón, then take in the social whirl of the Vedado district’s 23rd Avenue (La Rampa), the iconic Hotel Nacional de Cuba and the monumental Plaza de la Revolución.

Cross to the eastern side of the harbour to admire the 17th-century Castillo de los Tres Reyes Magos del Morro. This castle’s neighbour, the huge 18th-century Fortaleza de San Carlos de la Cabaña, the largest fort in Latin America, houses a museum dedicated to Che Guevara. Back on deck, listen out at 9pm for the cañonazo, a ceremonial firing of cannon, which can be heard every evening, booming across the harbour.

Cigars and coffee

Stop for a Cuban cafecito (espresso) or ice cream under the awnings of Café el Escorial on the restored Plaza Vieja. Dreaming of an authentic Cuban cigar? The atmospheric Hotel Conde de Villanueva (Mercaderes, corner of Lamparilla;, with its renowned cigar shop La Casa del Habano (official purveyor of Cuban smokes), is a five-minute walk from the cruise terminal. In February Havana hosts an annual cigar festival (, which draws connoisseurs from around the world. At Plaza de Armas, just off the port road, browse the second-hand book market before stopping off at the San José shopping warehouse, south of the cruise terminal.

A seven-night Cuba cruise on Star Flyer (0808 231 4798; ) departs the port of Cienfuegos on December 21 for the beaches of Playa Ancon, Casilda, Cayman Brac and Grand Cayman; returning to Cuba to visit Cayo Largo and Cayo Rico. Christmas Day will be spent in Georgetown, Grand Cayman. From £1,345 per person excluding flights.

An 11-night stay-and-sail holiday, departing on February 12 2015, with four nights in a four-star hotel in Havana costs from £2,439pp including return flight and transfers.


Claire Boobbyer, The Daily Telegraph
October 17, 2014

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