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.

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.

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.

Elegant and old, this relatively hush city spells oasis to the traveler weary of confrontation. Predating both Havana and Santiago, it has been cast for time immemorial as the city that kick-started Cuban independence. Yet self-important it isn't. The ciudad de los coches (city of horsecarts) is an easygoing, slow-paced, trapped-in-time place, where you're more likely to be quoted literature than sold trinkets. Cuba's balmiest provincial capital, it resounds to the clip-clop of hooves; nearly half the population use horses for daily travel.

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.

La Victória de Las Tunas (as it's officially known) is a sleepy agricultural town anointed provincial capital. It has long held a sleazy reputation for being the Oriente's capital of sex tourism. But thanks to good private lodgings, welcoming locals and a handy location on Cuba's arterial Carretera Central, handfuls of road-weary travelers drop by and are pleasantly surprised. Missing here are the touts that exasperate tourists in other destinations. It's a window into real provincial life.

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.

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.

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.

Tobacco is still king on Cuba's western fingertip, a rolling canvas of rust-red oxen-furrowed fields, thatched tobacco-drying houses and sombrero-clad guajiros (country folk).