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.

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).

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.

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.