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 3 Niebla, Chile

Niebla is a small village on the banks of the Rio Valdivia where Chile's Corral Bay meets the Pacific Ocean. Today Niebla is a beach resort, but in 1671 it was a defensive fortress built by the order of the Viceroy of Peru to prevent attacks against the town of Valdivia by pirates and corsairs. Niebla is well-known for its lively markets, the remains of the colonial fortress declared a National Monument in 1950 and restored in 1992, and a museum dedicated to its history. Nearby is the charming river port city of Valdivia, where cultural influences from the native Mapuche, Spanish settlers, and German immigrants have blended.

Day 4 Puerto Montt, Chile

For most of its history, windy Puerto Montt was the end of the line for just about everyone traveling in the Lake District. Now the Carretera Austral carries on southward, but for all intents and purposes Puerto Montt remains the region's last significant outpost, a provincial city that is the hub of local fishing, textile, and tourist activity.Today the city center is full of malls, condos, and office towers—it's the fastest-growing city in Chile—but away from downtown, Puerto Montt consists mainly of low clapboard houses perched above its bay, the Seno de Reloncaví. If it's a sunny day, head east to Playa Pelluco or one of the city's other beaches. If you're more interested in exploring the countryside, drive along the shore for a good view of the surrounding hills.

Day 5 Castro, Chile

Bright, wooden huts teeter on stilts over Castro's estuary waterfront, inviting you into a patchwork of colour that's sure to brighten any day. These traditional palafitos give the warmest of welcomes, as you prepare to experience Chile at its most vibrant. Castro has faced something of a tumultuous past, having been hit by a by a succession of earthquakes and fires - the most recent a devastating earthquake in 1960. But this city is incredibly resilient, and today the capital of Chiloe Island makes for a fantastic base for exploring the archipelago that surrounds it.  

Day 7 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 8 Chilean Fjords, Chile

Strewn through the coast of Chile, these beautiful fjords are world renowned for being one of the most awe-inspiring places on earth. Snow-capped volcanoes nestle majestically alongside rolling valleys of ice and frosty glaciers. Rugged beauty, breathtaking scenery not to mention diverse and profuse wildlife abounds – expect to watch whales from the deck, see playful Magellan Penguins and perhaps even spot the rare Andean Condor. Affectionately named “The End of the World” by the Spaniards who discovered the region in eighteenth century in a quest to Christianise South America, these extraordinary waterways not only encompass a medley of jagged mountains and iceberg strewn bays, but feature a kaleidoscopic spectrum of unexpected colour that offers photographic opportunities like no other destination.

Day 9 Chilean Fjords, Chile

Strewn through the coast of Chile, these beautiful fjords are world renowned for being one of the most awe-inspiring places on earth. Snow-capped volcanoes nestle majestically alongside rolling valleys of ice and frosty glaciers. Rugged beauty, breathtaking scenery not to mention diverse and profuse wildlife abounds – expect to watch whales from the deck, see playful Magellan Penguins and perhaps even spot the rare Andean Condor. Affectionately named “The End of the World” by the Spaniards who discovered the region in eighteenth century in a quest to Christianise South America, these extraordinary waterways not only encompass a medley of jagged mountains and iceberg strewn bays, but feature a kaleidoscopic spectrum of unexpected colour that offers photographic opportunities like no other destination.

Day 10 Chilean Fjords, Chile

Strewn through the coast of Chile, these beautiful fjords are world renowned for being one of the most awe-inspiring places on earth. Snow-capped volcanoes nestle majestically alongside rolling valleys of ice and frosty glaciers. Rugged beauty, breathtaking scenery not to mention diverse and profuse wildlife abounds – expect to watch whales from the deck, see playful Magellan Penguins and perhaps even spot the rare Andean Condor. Affectionately named “The End of the World” by the Spaniards who discovered the region in eighteenth century in a quest to Christianise South America, these extraordinary waterways not only encompass a medley of jagged mountains and iceberg strewn bays, but feature a kaleidoscopic spectrum of unexpected colour that offers photographic opportunities like no other destination.

Day 11 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).

Day 14 Antarctic Sound, Antarctica

The Antarctic Sound is a stretch of water named after the first ship to have passed through this body of water from the Bransfield Strait to the Weddell Sea in 1902. The Antarctic eventually sank and crew and scientists had to spend quite some time in this area before they could be rescued. Sites that have to do with this story - like Hope Bay or Paulet Island - are sometimes visited. At Paulet, Hope Bay and Brown Bluff Adelie and Gentoo Penguins breed, as do Kelp Gulls and Cape Petrels, Snow Petrels and Skuas. The Sound's main attractions are the spectacular tabular icebergs that come from the Larsen Ice Shelf further south.

Day 15 Antarctic Peninsula, Antarctica

Remote and otherworldly, Antarctic is irresistible for its spectacular iceberg sculptures and calving glaciers, and for the possibility of up-close encounters with marine mammals and the iconic penguins. The Antarctic Peninsula – the main peninsula closest to South America – has a human history of almost 200 years, with explorers, sealers, whalers, and scientists who have come to work, and eventually intrepid visitors coming to enjoy this pristine and remote wilderness. It is a region of protected bays, unscaled snow-capped mountains, vast glaciers and a few places where whalers or scientists have worked. Just as irresistible are the many Gentoo and Chinstrap Penguin colonies, the seals basking on ice floes, the whales and orcas.

Day 16 Antarctic Peninsula, Antarctica

Remote and otherworldly, Antarctic is irresistible for its spectacular iceberg sculptures and calving glaciers, and for the possibility of up-close encounters with marine mammals and the iconic penguins. The Antarctic Peninsula – the main peninsula closest to South America – has a human history of almost 200 years, with explorers, sealers, whalers, and scientists who have come to work, and eventually intrepid visitors coming to enjoy this pristine and remote wilderness. It is a region of protected bays, unscaled snow-capped mountains, vast glaciers and a few places where whalers or scientists have worked. Just as irresistible are the many Gentoo and Chinstrap Penguin colonies, the seals basking on ice floes, the whales and orcas.

Day 17 Antarctic Peninsula, Antarctica

Remote and otherworldly, Antarctic is irresistible for its spectacular iceberg sculptures and calving glaciers, and for the possibility of up-close encounters with marine mammals and the iconic penguins. The Antarctic Peninsula – the main peninsula closest to South America – has a human history of almost 200 years, with explorers, sealers, whalers, and scientists who have come to work, and eventually intrepid visitors coming to enjoy this pristine and remote wilderness. It is a region of protected bays, unscaled snow-capped mountains, vast glaciers and a few places where whalers or scientists have worked. Just as irresistible are the many Gentoo and Chinstrap Penguin colonies, the seals basking on ice floes, the whales and orcas.

Day 18 South Shetland Islands, Antarctica

Some 770 kilometers (478 miles) south of Cape Horn, the South Shetland Islands are usually the first land seen in Antarctica. Separated from the Antarctic Peninsula by the Bransfield Strait, nine major islands make up the group. The region was the first to be exploited by sealers in the early 19th century, and because of its proximity to South America, it still is the most visited by scientists and tourists. Chinstrap, Adelie, Gentoo and Macaroni Penguins all breed here. In addition, because it is the warmest part of the continent, large moss beds as well as orange, black, grey and green lichens grow –even hair grass and pearlwort manage to survive. Leopard seals, Weddell seals, crabeater seals, Southern elephant seals and Antarctic fur seals can be seen in the water and on the beaches.

Day 20 Puerto Williams, Chile

Day 21 Puerto Williams, Chile