Kuba

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.

This small but well-endowed province is Cuba at its loveliest, also guarding a precious chunk of the country's fantastical historical legacy. Sancti Spíritus Province boasts nature worth exploring. The best on Cuba’s underwhelming south coast, Playa Ancón is a stunner. And then there are mountains. Outside Trinidad, the haunting Escambray offers outstanding hiking on a network of picturesque trails.

Diminutive Ciego de Ávila's finger-in-the-dyke moment came during the late-19th-century Cuban Wars of Independence: it became the site of an impressive fortified wall, the Trocha, built to keep out rebellious eastern armies from the prosperous west. Today, the province continues to be the cultural divide between Cuba's Oriente and Occidente. Most tourists come here for the ambitious post–Special Period resort development of Cayo Coco and Cayo Guillermo. The brilliant tropical pearls that once seduced Ernest Hemingway have had their glorious beaches spruced up and daubed with over a dozen exclusive resorts.

Playa Larga, several kilometers south of Boca de Guamá at the head of the Bahía de Cochinos (Bay of Pigs), was one of two beaches invaded by US-backed exiles on April 17, 1961 (although Playa Girón, 35km further south, saw far bigger landings). Nowadays, it's the best base for exploring the Zapata peninsula, Cuba's largest wilderness area, and is also known for its diving (although Playa Girón makes a better base for the latter activity). There's a cheapish resort here, a scuba-diving center, and a smattering of casas particulares in the adjacent beachside village of Caletón.

Few parts of the world get named after yachts, which helps explain why in Granma (christened for the boat that delivered Fidel Castro and his bedraggled revolutionaries ashore to kick-start a guerrilla war in 1956) Cuba's viva la Revolución spirit burns most fiercely. This is the land where José Martí died and where Granma native Carlos Manuel de Céspedes freed his slaves and formally declared Cuban independence for the first time in 1868.

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.

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.

Varadero, located on the sinuous 20km-long Hicacos Peninsula, stands at the vanguard of Cuba’s most important industry – tourism. As the largest resort in the Caribbean, it guards a huge, unsubtle and constantly evolving stash of hotels (over 60), shops, water activities and poolside entertainment; though its trump card is its beach, an uninterrupted 20km stretch of blond sand that is undoubtedly one of the Caribbean's best. But, while this large, tourist-friendly mega-resort may be essential to the Cuban economy, it offers little in the way of unique Cuban experiences.

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.

The sandy arc of Playa Girón nestles peacefully on the eastern side of the infamous Bahía de Cochinos (Bay of Pigs), backed by one of those gloriously old-fashioned Cuban villages where everyone knows everyone else. Notorious as the place where the Cold War almost got hot, the beach is actually named for a French pirate, Gilbert Girón, who met his end here by decapitation in the early 1600s at the hands of embittered locals. In April 1961 it was the scene of another botched raid, the ill-fated, CIA-sponsored invasion that tried to land on these remote sandy beaches in one of modern history's classic David-and-Goliath struggles. Lest we forget, there are still plenty of propaganda-spouting billboards dotted around rehashing past glories.