Play your cards right in Cuba's capital

Fifties mobsters had glittering plans for a Las Vegas of the Caribbean in Havana, says Claire Boobbyer

American mobster Meyer Lansky had a dream. He wanted Havana to bloom as the Las Vegas of the Caribbean; he wagered millions on his money-making vision – even building his own pleasure palace on the city's seaside highway, the Malecón.

The Hotel Riviera, clad in a sheen of shimmering turquoise mosaic, with its casino and coffin-shaped pool, was the last word in hotel luxury when Ginger Rogers sang her way through the opening night in 1957. Extraordinarily, the Riviera (Paseo y Malecón; 00 53 7 836 4051; www.gran-caribe.cu) remains virtually unchanged in the city's upmarket Vedado district. You can still check into Lanksy's rooms, numbers 1923-24.

The glamorous Hotel Riviera was just one of several temples to unbridled hedonism that hatched across 1950s Havana, as an entertainment and building boom scurried across Vedado, in large part due to a hotel law – bristling with tax incentives – passed by President Fulgencio Batista.

Head four blocks south and turn left along Linea, passing a curious Cuban hybrid– the Synagogue Beth Shalom and Café Teatro Bertolt Brecht. Built in 1953 as a Jewish religious and community complex, the building was halved in 1981 and sold to the Ministry of Culture to raise funds. Today's synagogue (Calle I, corner of 13; 00 53 7 832 8953) is conjoined with one of the city's hippest haunts where cool young things sip cocktails and beers at the curved red bar (00 53 7 830 1354).

Walking four blocks east on Linea brings you to Calle M and the austere minty green and cream 1956 Focsa Building. The largest building in Cuba with 400 apartments, its 33rd-floor La Torre bar (Calle 17 e/ M y N; 00 53 7 838 3088) offers wide-angled views of the city. Meanwhile, the ground-floor El Emperador bar and restaurant, although altered, is a lavish, dimly lit 1956 creation, perfect for photophobic punters.

Just south of the Focsa is 1950s penthouse paladar Café Laurent, one of Havana's best new diners (Calle M 257 e/19 y 21; 00 53 7 831 2090; cafelaurent.ueuo.com) plastered in American monochrome magazine pages from the 1950s.

Heading one block east along Calle 21 is the Hotel Capri (Calle N e/ 19 y 21; 00 53 7 833 3747; www.gran-caribe.cu), the 1956 mob-built pleasure parlour. Its roof-top pool featured in the opening long shot of the 1964 Soviet-Cuban movie Soy Cuba and Michael Corleone also stayed there in Francis Ford Coppola's The Godfather Part II. The Capri is currently closed for refurbishment and is set to reopen in July. One block further east is the imposing 1930s Hotel Nacional (Calle O corner of 21, 00 53 7 836 3564; hotelnacionaldecuba.com). In 1946, a mafia conference, where roast flamingo and manatee were served, was held in the hotel (tours Monday-Friday 10am, 4pm, Saturday 10am; free). Here, the Cosa Nostra cooked up their Sin City plans for Havana.

Cross Calle 23 (La Rampa) before turning left along Calle 25 and popping up to see Casa Abel Santamaría (Calle 25 No 164 e/ O y Infanta; 00 53 7 835 0891). In the spartan apartment, rebels Fidel Castro and Abel Santamaria devised their 1953 assault on Santiago de Cuba's barracks – the catalyst for the 1959 revolution that toppled the dictator Batista.

While the mobsters gambled on a takeover of Havana's leisure industry, Castro and his acolytes plotted the downfall of the regime that had stoked Havana's ribald nightlife. Nowhere was this louche world more in evidence than around La Rampa. At the end of Calle 25 is the pink, castellated former bordello La Marina, the most famous such establishment (now a Malecon café). Walking west along the Malecon, turn up La Rampa. On the corner of Calle 23 and Calle P is the ruined Cabaret Montmartre which, along with the Sans Souci, and the sequinned spectacle at the surviving Tropicana (www.cabaret-tropicana.com) were considered the unholy trinity of late-night leisure in 1950s Havana, frequented by North American hedonists, libertines – and Graham Greene.

Walk uphill past 1950s Cine La Rampa to Hotel Habana Libre (Calle L e/ 23 y 25; 00 53 7 834 6100; melia.com) opened by Hilton at a cost of $24m in 1958. Regrettably, the building has been much altered, but the allure for today's visitor is the almost original Trader Vic's Tiki restaurant (today, El Polinesio). When Castro and his rebel army marched into Havana in 1959, hotel rooms provided their headquarters (Suite Presidencial "La Castellana", room 2224, was the revolution command post).

From here, step back on to the Rampa and hail a classic 1950s chrome-finned American taxi, requesting the "por Prado" route (C$0.50/30p). As the car rumbles down San Lazaro, it passes wide Galiano, also known as Avenida de Italia. On the left, look out for the mob-built Hotel Deauville with its pint-sized pool in the sky (Calle Galiano 1 e/ San Lazaro y Malecon; 00 53 7 866 8812; www.gran-caribe.cu).

At Prado, get out at the corner of Calle Trocadero and cross the central promenade passing the Moorish Hotel Sevilla (Trocadero e/ Prado y Agramonte; 00 53 7 860 8560; accorhotels.com) where Al Capone bedded down in room 615. Wander east on Trocadero past the Granma, the yacht that carried Castro's rebel 26 July movement from Mexico to Cuba in 1956, in the grounds of the former Presidential Palace. Head south down Calle Monserrate, taking a left skirting the Art Deco Bacardi building. On the corner of Calle Villegas and San Juan de Dios, rummage through the curios, including 1950s memorabilia, at shop Casa de Carlos. Retrace your steps to Monserrate, then walk one block north (right) and amble one block west (left) along Calle Animas to its corner with Agramonte.

Slink up to the bar of the newly reopened Sloppy Joe's, the favoured drinking hole of tipsy tourists from the Twenties through to the Fifties. This world-original Sloppy Joe's, which appeared in Carol Reed's film of Graham Greene's Our Man in Havana, was shut in the Sixties; the new bar, once again, concocts chilled cocktails for global flâneurs – and perhaps the odd spy – to slake their thirst.

Fresh cuts

Glass-fronted Hotel Terral, with two penthouse suites and 12 smart rooms, faces the sea (Malecón corner of Lealtad, Centro; 00 53 7 860 2100; habaguanex.ohc.cu). The delicious all-you-can-eat breakfast (C$10/£6.50) is a steal.

Casa Miglis is a stylish Swedish restaurant in Centro (Lealtad 120 e/Animas y Lagunas; casamiglis.com). Inside is the wonky-furnitured Bar Imapla; owner Michel is soon to open patio DJ bar Miglis there too.

Travel essentials

Getting there

The Holiday Place (020-7644 1755; holidayplace.co.uk) offers holidays to Havana, including stays at the Riviera, Nacional and Habana Libre, from £759 per person for seven nights including flights from Gatwick.

Virgin Atlantic (0844 2092 770; virginatlantic.com) flies twice weekly from Gatwick to Havana from £667. Air Europa (0871 423 0717; aireuropa.com) flies 10 times a week, from Gatwick via Madrid, from £732.

More information

Travel2cuba.co.uk

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