Kuba

Trinidad is one of a kind, a perfectly preserved Spanish colonial settlement where the clocks stopped in 1850 and – apart from a zombie invasion of tourists – have yet to restart. Huge sugar fortunes amassed in the nearby Valle de los Ingenios during the early 19th century created the illustrious colonial-style mansions bedecked with Italian frescoes, Wedgwood china and French chandeliers.

Habana del Este is home to Playas del Este, a multiflavored if slightly unkempt beach strip situated 18km east of Habana Vieja. While the beaches here are sublime, the accompanying resorts aren't exactly luxurious. Rather, Playas del Este has a timeworn and slightly abandoned air, and aspiring beach loungers might find the ugly Soviet-style hotel piles more than a little incongruous. But for those who dislike modern tourist development or are keen to see how Cubans get out and enjoy themselves, Playas del Este is a breath of fresh air.

A historic refuge from the law for everyone from 16th-century pirates to 20th-century gangsters, La Isla is perhaps the quirkiest castaway destination you ever will see. Dumped like a crumpled apostrophe 100km off mainland Cuba, this pine-tree-clad island is the Caribbean's sixth-largest. But the Cayman Islands this isn't. Other tourists? Uh-uh. And if you thought mainland Cuba's towns were time-warped, try blowing the dust off island capital Nueva Gerona, where the main street doubles as a baseball diamond, and the food ‘scene’ is stuck in the Special Period. Yet, if you make it here, you're in for a true adventure. The main lure is diving some of the Caribbean's most pristine reefs, but otherwise get used to being becalmed with the coral, the odd crocodile and a colorful history that reads like an excerpt from Treasure Island.

In his song 'Cienfuegos,' Benny Moré described his home city as the city he liked best. He wasn't the settlement's only cheerleader. Cuba's so-called 'Pearl of the South' has long seduced travelers from around the island with its elegance, enlightened French airs and feisty Caribbean spirit. If Cuba has a Paris, this is most definitely it.

Matanzas is like a sunken galleon left at the bottom of the ocean. Most casual visitors to Cuba sail right over the top of it (usually on a tour bus to Varadero), but, a few curious adventurers dive down and discover that this ostensibly scruffy city is still full of priceless treasure. Go back a few generations and Matanzas was a very different place. During the 18th and 19th centuries, the city developed a gigantic literary and musical heritage, and was regularly touted as the ‘Athens of Cuba.' Two pivotal Cuban musical forms, danzón and rumba, were hatched here, along with various religions of African origin. Matanzas also hosts one of Cuba’s finest theaters, and was the birthplace of some of its most eloquent poets and writers. Despite the contemporary aura of decay, the cultural riches haven’t disappeared. You just need patience, imagination and a Sherlock Holmes hat to disentangle them.

Majestic, spread-out Vedado is Havana's once-notorious Mafia-run district. During Cuba's 50-year dalliance with the US, this was the city's commercial hub and, in many ways, it still is; although these days the nightlife is less tawdry, the casinos have become discos, and the hotels seem more like historical relics than havens of luxury.

A fantasy land of crinkled mountains and exuberant foliage, the Cuban Guantánamo remains a galaxy away from modern America in ambience. That doesn't stop most people associating it with the United States Guantanamo Bay Naval Base, which continues in operation, though downsized. Off the base, the region’s isolated valleys and wild coastal microclimates (arid in the south, lush in the north) are Cuba at its most mysterious and esoteric. Herein lie primitive musical subgenres, little-known Afro-Cuban religious rites, and echoes of an indigenous Taíno culture supposedly wiped out by the Spanish centuries ago – or so you thought.

Havana's Old Town – the site where the city first took root in 1519 – is one of the historical highlights of Latin America, an architectural masterpiece where fastidiously preserved squares and grandiose palaces sit alongside a living, breathing urban community still emerging from the economic chaos of the 1990s. The overall result is by turns grand and gritty, inspiring and frustrating, commendable and lamentable. No one should leave Cuba without seeing it.

The nation’s fourth-largest city serves up authentic provincial Cuba without the wrapping paper. Though the city of San Isidoro de Holguín barely features in Cuba’s tourist master plan, there’s magic and mystery here for a certain type of traveler. There's an overabundance of shiny vintage Chevys, plazas filled with uniformed school children sharing wi-fi and interactions not marred by rushing or selling. Use it as a window to life in the interior: from the religious solemnity of the annual procession climbing Loma de la Cruz to the exuberant cheers pouring forth from the oversized baseball stadium.

Cuba's third-largest city is easily the suavest and most sophisticated after Havana. The arts shine bright here and it's also the bastion of the Catholic Church on the island. Well known for going their own way in times of crisis, its resilient citizens are called agramontinos by other Cubans, after local First War of Independence hero Ignacio Agramonte, coauthor of the Guáimaro constitution and courageous leader of Cuba's finest cavalry brigade.