This large, modern port serves Chile’s capital, Santiago, a city with Spanish colonial charm and a vivacious spirit. Encircled by the Andes and the Coastal Range, Santiago is centered around the Plaza de Armas, with several of the city’s landmarks: the 18th-century Metropolitan Cathedral the Palacio de la Real Audencia from 1808, the City Hall and the National Museum of History. North of San Antonio lie the picturesque old port and university town of Valparaíso and the colorful seaside resort of Viña del Mar. In between the coast and the capital are valleys filled with some of Chile’s most famous wineries, all inviting you to come and taste.

Gateway to the scenic Lake District, a series of fragrant eucalyptus and pine forests, icy lakes, Bavarian hamlets and luminous snowcapped volcanoes. Sample shore excursions: Alerce Mountain Lodge & Lake of Reflections; Petrohué Rapids & Frutillar.

Here in the heart of the Chilean archipelago, discover stunning scenery: dense rain forests, bright-blue lakes and snow-covered mountain peaks. Sample shore excursions: Sights of Patagonia; Lake Elizalde Adventure.

If Punta Arenas exudes an “edge of the world” air, it’s not without reason. This windblown city near Chile’s southernmost tip sits on the Strait of Magellan, which itself is positioned squarely between the Atlantic and Pacific oceans. The city has played—and continues to play—an important role in geographic, political and economic affairs in South America’s so-called Southern Cone, which is formed by Chile and neighboring Argentina. Too many travelers rush through Punta Arenas, treating it as a pit stop on their way to the stunningly beautiful landscapes of Torres del Paine National Park and other attractions in Patagonia, but there’s plenty in this city and its environs to experience, too. From penguin spotting on Isla Magdalena and kayaking the Strait of Magellan to visiting area farms and then indulging in surf-and-turf specialties (here meaning fresh seafood and asado, or Chilean barbecue) at local restaurants, Punta Arenas is worth a stopover all its own.

Dramatic, fantastical, otherworldly—this is the end of the world, for real. Positioned at the southernmost tip of Argentina, this memorable port town is cradled between the pristine—and towering—Martial Mountains and accessed by the picturesque Beagle Channel (which was named for Darwin’s famed vessel). Ushuaia is the capital of the Tierra del Fuego region, which is best described as a spectacular collection of superlative natural wonders. It’s a veritable kaleidoscope of glittering glaciers, snowcapped mountains, dense forests, sparkling lakes and windswept plains spread across an archipelago of rugged islands.

The town itself is a maze of streets lined with low-slung buildings that all seem to meet at its heart, the port. Founded in 1884, the far-flung spot welcomed missionaries, gold prospectors and naval officers before becoming known primarily as a penal colony. After its closure under the infamous Argentine leader Juan Perón, the large jail was reconfigured to house one of the city’s most popular museums. Other current in-town attractions include a maritime museum and a museum dedicated to the region’s natural history, as well as restaurants preparing the marquee offering—local king crab.

It may be the most notorious ocean passage in the world, and for centuries it evoked dread in the hearts of sailors. But those who survived a trip around Cape Horn, where the Atlantic and Pacific slosh violently into each other, had bragging rights for life. Along this passage, the Tierra del Fuego, or “land of fire,” where Chile and Argentina converge at the bottom of the world, got its name from early sailors who saw the fires of the people who lived here burning on shore. For some 8,000 years, until as recently as the end of the 19th century, this was the home of the Yaghan and other indigenous groups.

Magellan and Drake left their mark and names here, as did Darwin, who sailed through here on the HMS Beagle. The great clipper ships of ’49er lore later fought their way through fierce waves carrying gold between California and the East Coast in that era before the Panama Canal. Just as Richard Henry Dana, Jr., described in his masterful Two Years Before the Mast, published in 1840, a journey today around the Cape at the very bottom of the Tierra is shaped by capricious weather, as powerful winds and shallow waters can produce waves that reach as high as 30 meters (100 feet).

The world’s southernmost capital, Stanley is located in the Falklands archipelago, which consists of two main islands, East and West Falkland, along with smaller islands nearby. Stanley is proud of its British heritage, evidenced everywhere from its red telephone boxes to its pubs. The Falklands were first claimed by the English in 1765; over the centuries the Crown has had to abandon, reclaim and defend these far-flung islands from invading nations—including an Argentine foray in 1982. During the early years of their colonization, the Falklands were used as a base for ships hunting sperm whales for oil, followed by those hunting seals for fur. Today in this remote British territory, fishing and tourism are what drive the economy.

Situated in rugged Argentine Patagonia, Puerto Madryn was founded by Welsh immigrants in 1865. Enjoy a famous Welsh “tea” in the village of Gaiman; journey back in time 300 million years at the Paleontology Museum of Egidio Feruglio in Trelew; and see colonies of sea elephants, sea lions and seals in their natural habitat at Punta Norte. Sample shore excursions: Punta Tombo Penguin Adventure; Peninsula Valdes Natural Reserve; Puerto Madryn Private Touring.

Known as the St. Tropez of Uruguay for its miles of beautiful, pristine beaches, sports activities, shopping, and temperate climate, Punta del Este offers something for everyone. Choose a gentle bayside beach or dramatic Atlantic beach with perfect surfing waves; explore the colonial and modern architecture of downtown and shop for local treasures; and visit Casa del Pueblo – a modern art museum that was once the home of celebrated Uruguayan artist Carlos Paez Vilaro.

Friendly and genteel, Montevideo honors colonial customs: long lunches, siestas, high tea. Nearby: Colonia del Sacramento, the oldest city in Uruguay (ca. 1680) and a UNESCO World Heritage Site. Sample shore excursions: Colonia del Sacramento; A Gaucho’s Life.

In the early 20th century, Buenos Aires, Argentina, gained immense wealth when it began shipping its pampas-raised beef around the world. It quickly entered the club of great world cities, and a slew of attractions and architectural jewels soon arose. Since that time, the capital has experienced huge swings in economic and political fortune. But Buenos Aires continues to fascinate and entertain sightseeing visitors, both for its chaotic energy and for its sheer urban beauty. Thankfully, the Belle Époque grandeur and enormous tracts of greenery remain. Any list of things to do in Buenos Aires would begin with its many walkable neighborhoods; Palermo especially stands out, thanks to creative residents who have pushed the restaurant scene well beyond beef.

Porteños—as the locals are called—may be of Spanish, Italian, Jewish or Middle Eastern descent; that mix of cultures is reflected in the city’s dialect, foods and pastimes. Looking beyond the city’s sights, Buenos Aires is known as the birthplace of tango, and while the music and dance never quite went away, today tango is making a resurgence. Fans come here from around the world to take part in or watch the milongas (dance events). Argentines are world leaders in polo as well, and as the sport captures the interest of more and more travelers, hunky players like Nacho are gaining global celebrity.

In the early 20th century, Buenos Aires, Argentina, gained immense wealth when it began shipping its pampas-raised beef around the world. It quickly entered the club of great world cities, and a slew of attractions and architectural jewels soon arose. Since that time, the capital has experienced huge swings in economic and political fortune. But Buenos Aires continues to fascinate and entertain sightseeing visitors, both for its chaotic energy and for its sheer urban beauty. Thankfully, the Belle Époque grandeur and enormous tracts of greenery remain. Any list of things to do in Buenos Aires would begin with its many walkable neighborhoods; Palermo especially stands out, thanks to creative residents who have pushed the restaurant scene well beyond beef.

Porteños—as the locals are called—may be of Spanish, Italian, Jewish or Middle Eastern descent; that mix of cultures is reflected in the city’s dialect, foods and pastimes. Looking beyond the city’s sights, Buenos Aires is known as the birthplace of tango, and while the music and dance never quite went away, today tango is making a resurgence. Fans come here from around the world to take part in or watch the milongas (dance events). Argentines are world leaders in polo as well, and as the sport captures the interest of more and more travelers, hunky players like Nacho are gaining global celebrity.