I bought a ticket to Cuba in 1998 when Fidel Castro promised a Christmas Day holiday after a 30-year ban. The holiday itself was a tinsel-free affair, but I heard live music and caught a glimpse of Castro in the main square at Santiago de Cuba as he toasted the 40th anniversary of his revolution.
Since that first trip, I’ve danced, drunk, dived, fished, hiked, cycled and driven around Cuba. I’ve had my fortune told and portrait painted, ridden vintage American cars with no seats, picked up a spent bullet in the Bay of Pigs, and paraded through Havana on a giant fibre-glass stiletto.
Cuba is utterly bonkers and I love it, as do those who come in search of an offbeat sunny break. This year marks the 60th anniversary of the Cuban revolution but it’s not all austerity and rationed food. Since a change to private business rules almost a decade ago, this Caribbean island now offers holidaymakers swanky apartments in colonial villas, rural hideaways, beach getaways, bike tours and foodie experiences.
A fine vintage: Cuba is full of old American cars – as well as the world’s finest smokes and cigars
Beach babes head north
With 3,500 miles of coastline, where do you go for a fly-and-flop break? Skip the southern coastline – the turquoise waters and glossy palm trees of your dreams lie on the north coast. Most holidaymakers head for all-inclusive beach resorts such as Varadero, Cayo Santa Maria, the Gardens of the King archipelago (a hit with kite-surfers) and Guardalavaca .
MY TIP: Stay at Varadero’s Paradisus Princesa del Mar (doubles from £302 a night, meliacuba.com) or Angsana Cayo Santa Maria (doubles from £122 a night, angsana.com). Cayo Guillermo Resort Kempinski, the first resort with overwater villas in Cuba, is due to open later this year (kempinski.com).
Sample Churchill’s favourites
The world’s finest smokes are made in Cuba. Fidel Castro had Cohiba cigars especially crafted for him, while Winston Churchill puffed away on Romeo y Julietas. Tour a factory to watch cigars being hand-rolled (£8). Connoisseurs will want to see Cuba’s tobacco heartland in the south-west of the island. Sign up for an expert tour with a fine farm lunch at Hector Luis Prieto’s plantation (£10, hectorfinca.com).
Be careful to buy cigars from Habanos state-run stores only – those purchased from street vendors may be stuffed with worthless filler.
MY TIP: You’ll get taken to the tobacco-growing heartland over three days when you sign up for a Cuba Welcome tour (£340pp, cubawelcome.com).
Pirates of the Caribbean
Swashbuckling pirates have left traces all over Cuba. Fabulous forts to fend off buccaneers can be seen in Havana, Santiago and Baracoa. You’ll find Castro’s 1959 guerrilla hideout in the Sierra Maestra range, or you could duck into secret tunnels used by his government during the 1962 Cuban missile crisis on a history tour organised by Hotel Nacional (free for hotel guests or £4 for visitors, hotelnacionaldecuba.com).
You’ll find Che Guevara’s memorial and tomb at Santa Clara city.
MY TIP: After visiting Che Guevara sites in Santa Clara, relax with a coffee at Cafe-Museo Revolucion, which is dedicated to all things Che (facebook.com/cafemuseorevolucion).
Take to the water
Coming face to face with a black grouper off the coast of Cuba. You can take a week-long boat trip in the Gardens of the Queen area and dive with sharks, turtles, giant groupers and even a friendly croc called Nino
Explorer Jacques Cousteau is credited with inspiring Fidel Castro to protect the seas close to Cuba when he sailed around the island on Calypso in 1985. Virtually unknown to divers for years, Cuba’s marine-life secrets are now out.
You can take a week-long boat trip in the Gardens of the Queen area and dive with sharks, turtles, giant groupers and even a friendly croc called Nino.
If a week on a dive boat is too long, slip in from the shore at the Bay of Pigs to spy a huge coral wall and Cold War wrecks, dive down to explore shipwrecks off Santiago, or spot turtles off the remote Isle of Youth’s Punta Frances.
MY TIP: Avalon (cubandivingcenters.com) runs week-long full-board dive trips on yachts (from £2,911pp) to the Gardens of the Queen.
Make mine a cocktail
Facundo Bacardi Masso discovered the secrets of ageing rum in the country’s second city, Santiago, in 1862. Rum drinker Ernest Hemingway’s Havana exploits still propel visitors through the doors of El Floridita (for a daiquiri) and La Bodeguita (for a mojito) but there are better spots. Join mixologists at Old Havana’s coolest spot, El del Frente (facebook.com/Eldel Frente303) for a hands-on session (£20pp), or pair cigars with rum in the Evocacion Tobacco Lounge at the Cuban capital’s five-star Gran Hotel Manzana Kempinski (from £24pp, kempinski.com).
MY TIP: Try the passion fruit cocktail at Michifu in Havana, or head for the terrace bar of Hotel Casa Granda, a former haunt of Graham Greene in Santiago de Cuba (iberostar.com).
Listen up and dance
A performance at the Fabrica de Arte club. Cuba’s music is infectious. For top salsa clubs and live bands, hit the clubs of Havana, Santiago, Trinidad and Baracoa
Whether it’s Enrique Iglesias’s mega-hit Bailando or some Buena Vista Social Club classics, Cuba’s music is infectious. For top salsa clubs and live bands, hit the clubs of Havana, Santiago, Trinidad and Baracoa. For rumba, head to Matanzas. If ballet is more your thing, don’t miss the dazzling Havana Grand Theatre headliners.
Fancy taking a dance lesson during your break? Book in with maestros of movement Salsaencasa (£12 an hour, salsaencasa.com).
MY TIP: Catch a live performance at Havana’s Fabrica de Arte Cubano (fac.cu), or watch salsa bands at Casas de la Trova in Santiago de Cuba (promociones.egrem.co.cu).
Feast not famine
From artisanal ice cream to homemade bread, and from sashimi to vegetarian, you can dine very nicely in Cuba now. Shortages still occur but options are plentiful. Foodie hotspots can be found in Havana, Vinales and Baracoa.
MY TIP: Order slow-roasted suckling pig at Ivan Chefs Justo in Havana (facebook.com/IvanChefs Justo/) or savour roast chicken and delicious garden salads at El Cuajani in Vinales (facebook.com/restauranteelcuajani).
Cuba’s colonial conquerors knew prime real estate when they first glimpsed Cuba back in 1492. Tour the first island capital, Baracoa, the preserved splendour of tourist honeypot Trinidad, elegant French-founded Cienfuegos, the plaza-and-church-stuffed Camaguey, the quieter Sancti Spiritus, musical Santiago, and, of course, soul-stirring Havana, with its colourful mansions, churches, forts and fountains.
MY TIP: Make your way around Old Havana and check into a lavish two-bed apartment at Plaza Vieja 1912 (plazavieja1912.com), or tour Trinidad’s Cantero Palace and book into the elegant hacienda La Casona, with double bedrooms from £122 (lacasona759trinidad.com).
With epic mountain ranges studded with glorious royal palms, glassy rivers, and a coastline with perfect conditions for kite-surfing, the problem is trying to pack it all in.
MY TIP: Walk the sublime Vinales Valley with its pudding-bowl mountains, trek the Unesco-protected Alejandro de Humboldt National Park, or take stunning snaps at the Soroa waterfall at Pinar del Rio.