Valparaíso's dramatic topography—45 cerros, or hills, overlooking the ocean—requires the use of winding pathways and wooden ascensores (funiculars) to get up many of the grades. The slopes are covered by candy-color houses—there are almost no apartments in the city—most of which have exteriors of corrugated metal peeled from shipping containers decades ago. Valparaíso has served as Santiago's port for centuries. Before the Panama Canal opened, Valparaíso was the busiest port in South America. Harsh realities—changing trade routes, industrial decline—have diminished its importance, but it remains Chile's principal port. Most shops, banks, restaurants, bars, and other businesses cluster along the handful of streets called El Plan (the flat area) that are closest to the shoreline. Porteños (which means "the residents of the port") live in the surrounding hills in an undulating array of colorful abodes. At the top of any of the dozens of stairways, the paseos (promenades) have spectacular views; many are named after prominent Yugoslavian, Basque, and German immigrants. Neighborhoods are named for the hills they cover. With the jumble of power lines overhead and the hundreds of buses that slow down—but never completely stop—to pick up agile riders, it's hard to forget you're in a city. Still, walking is the best way to experience Valparaíso. Be careful where you step, though—locals aren't very conscientious about curbing their dogs.

When people discuss great South American cities, Lima is often overlooked. But Peru's capital can hold its own against its neighbors. It has an oceanfront setting, colonial-era splendor, sophisticated dining, and nonstop nightlife.It's true that the city—clogged with traffic and choked with fumes—doesn't make a good first impression, especially since the airport is in an industrial neighborhood. But wander around the regal edifices surrounding the Plaza de Armas, among the gnarled olive trees of San Isidro's Parque El Olivar, or along the winding lanes in the coastal community of Barranco, and you'll find yourself charmed.In 1535 Francisco Pizarro found the perfect place for the capital of Spain's colonial empire. On a natural port, the so-called Ciudad de los Reyes (City of Kings) allowed Spain to ship home all the gold the conquistador plundered from the Inca. Lima served as the capital of Spain's South American empire for 300 years, and it's safe to say that no other colonial city enjoyed such power and prestige during this period.When Peru declared its independence from Spain in 1821, the declaration was read in the square that Pizarro had so carefully designed. Many of the colonial-era buildings around the Plaza de Armas are standing today. Walk a few blocks in any direction for churches and elegant houses that reveal just how wealthy this city once was. But the poor state of most buildings attests to the fact that the country's wealthy families have moved to neighborhoods to the south over the past century.The walls that surrounded the city were demolished in 1870, making way for unprecedented growth. A former hacienda became the graceful residential neighborhood of San Isidro. In the early 1920s the construction of tree-lined Avenida Arequipa heralded the development of neighborhoods such as bustling Miraflores and bohemian Barranco.Almost a third of the country's population of 29 million lives in the metropolitan area, many of them in relatively poor conos: newer neighborhoods on the outskirts of the city. Most residents of those neighborhoods moved there from mountain villages during the political violence and poverty that marked the 1980s and ’90s, when crime increased dramatically. During the past decade the country has enjoyed peace and steady economic growth, which have been accompanied by many improvements and refurbishment in the city. Residents who used to steer clear of the historic center now stroll along its streets. And many travelers who once would have avoided the city altogether now plan to spend a day here and end up staying two or three.

Port Antonio, on the Northeast coast of Jamaica, is the islands third largest port, mainly for bananas and coconuts. It is also an important tourist destination. In fact, it has been featured as a model of paradise in several famous Hollywood films such as Club Paradise and Cocktail. Port Antonio was a sleepy coastal town until the 1880s, when Lorenzo Dow Baker, an American businessman, started the banana trade in Jamaica and promoted Port Antonio as a vacation spot for wealthy Americans. "Portie", as it is nicknamed, became a boom town. Even the movie star Errol Flynn was enamoured and ended up buying property here after his yacht washed ashore in 1946. Today it is still a major destination with plenty to do and see, from stunning scenery, creative arts and crafts, and cultural and historical sites.

From Wall Street's skyscrapers to the neon of Times Square to Central Park's leafy paths, New York City pulses with an irrepressible energy. History meets hipness in this global center of entertainment, fashion, media, and finance. World-class museums like MoMA and unforgettable icons like the Statue of Liberty beckon, but discovering the subtler strains of New York's vast ambition is equally rewarding: ethnic enclaves and shops, historic streets of dignified brownstones, and trendy bars and eateries all add to the urban buzz.