Day 1 Valparaiso, Chile

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.

Day 4 Quemchi, Chiloe Island, Chile

Day 6 Caleta Tortel, Chile

Tortel is a commune located in Southern Patagonia, a spectacular wilderness region of rugged mountains, glaciers, rivers and forests of infinite beauty. The uneven geography of Tortel shapes a unique landscape, characterized by an archipelagic area with numerous islands and channels. Tortel is known as the “footbridge city” for the unique beauty of its wooden walkways that connect the piers and houses of this quaint place through bridges and stairs, built from cypress wood, that run for four and a half miles around the cove and that respect the rich vegetation that grows under them. Even though it is the sixth largest commune in Chile, it has the lowest population of all with roughly 531 people. The history of the town dates back to 1520 when it was inhabited by nomadic Kawesqar, now extinct. Its definitive foundation was in 1955, after numerous attempts to populate the area. In 2001, it was declared by the Chilean government as a Picturesque Zone of National Heritage.

Day 7 PIO X Glacier, Chile

Day 8 El Brujo Glacier, Chile

Day 9 Estero las Montanas, Chile

Day 11 Alberto de Agostini National Park, Chile

Alberto de Agostini National Park was created in 1965 and takes its name from an Italian explorer, photographer, writer and missionary of the Salesians of Don Bosco order that lived and explored Patagonia as a missionary around 1930. De Agostini was known for his discoveries, photographs and maps of the region. The park is located in the Region of Magallanes and Chilean Antarctica, the southernmost, largest, and second least populated region of Chile. The park covers 5,637 square miles and touches Magallanes, Tierra del Fuego and Antarctica provinces. It is the third largest protected area of the country. The park was declared a World Biosphere Reserve by UNESCO in 2005 and protects many species of animals and sea birds. Its rich fauna includes species like the Andean fox, the South American grey fox (also known as the Patagonian fox), the southern elephant seal, the leopard seal, the Chilean dolphin (also known as the black dolphin or tonina), and the humpback whale.

Day 12 Garibaldi Glacier, Chile

Day 14 Puerto Williams, Chile

Day 15 Ushuaia, Argentina

At 55 degrees latitude south, Ushuaia (pronounced oo-swy-ah) is closer to the South Pole than to Argentina's northern border with Bolivia. It is the capital and tourism base for Tierra del Fuego, the island at the southernmost tip of Argentina.Although its stark physical beauty is striking, Tierra del Fuego's historical allure is based more on its mythical past than on rugged reality. The island was inhabited for 6,000 years by Yámana, Haush, Selk'nam, and Alakaluf Indians. But in 1902 Argentina, eager to populate Patagonia to bolster its territorial claims, moved to initiate an Ushuaian penal colony, establishing the permanent settlement of its most southern territories and, by implication, everything in between.When the prison closed in 1947, Ushuaia had a population of about 3,000, made up mainly of former inmates and prison staff. Today the Indians of Darwin's "missing link" theory are long gone—wiped out by diseases brought by settlers and by indifference to their plight—and the 60,000 residents of Ushuaia are hitching their star to tourism.The city rightly (if perhaps too loudly) promotes itself as the southernmost city in the world (Puerto Williams, a few miles south on the Chilean side of the Beagle Channel, is a small town). You can make your way to the tourism office to get your clichéd, but oh-so-necessary, "Southernmost City in the World" passport stamp. Ushuaia feels like a frontier boomtown, at heart still a rugged, weather-beaten fishing village, but exhibiting the frayed edges of a city that quadrupled in size in the '70s and '80s and just keeps growing. Unpaved portions of Ruta 3, the last stretch of the Pan-American Highway, which connects Alaska to Tierra del Fuego, are finally being paved. The summer months (December through March) draw more than 120,000 visitors, and dozens of cruise ships. The city is trying to extend those visits with events like March's Marathon at the End of the World and by increasing the gamut of winter activities buoyed by the excellent snow conditions.A terrific trail winds through the town up to the Martial Glacier, where a ski lift can help cut down a steep kilometer of your journey. The chaotic and contradictory urban landscape includes a handful of luxury hotels amid the concrete of public housing projects. Scores of "sled houses" (wooden shacks) sit precariously on upright piers, ready for speedy displacement to a different site. But there are also many small, picturesque homes with tiny, carefully tended gardens. Many of the newer homes are built in a Swiss-chalet style, reinforcing the idea that this is a town into which tourism has breathed new life. At the same time, the weather-worn pastel colors that dominate the town's landscape remind you that Ushuaia was once just a tiny fishing village, snuggled at the end of the Earth.As you stand on the banks of the Canal Beagle (Beagle Channel) near Ushuaia, the spirit of the farthest corner of the world takes hold. What stands out is the light: at sundown the landscape is cast in a subdued, sensual tone; everything feels closer, softer, and more human in dimension despite the vastness of the setting. The snowcapped mountains reflect the setting sun back onto a stream rolling into the channel, as nearby peaks echo their image—on a windless day—in the still waters.Above the city rise the last mountains of the Andean Cordillera, and just south and west of Ushuaia they finally vanish into the often-stormy sea. Snow whitens the peaks well into summer. Nature is the principal attraction here, with trekking, fishing, horseback riding, wildlife spotting, and sailing among the most rewarding activities, especially in the Parque Nacional Tierra del Fuego (Tierra del Fuego National Park).