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 2 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 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 6 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 7 Punta Arenas, Chile

Impenetrable forests, impassable mountains, and endless fields of ice define Chilean Patagonia, and meant that the region went largely unexplored until the beginning of the 20th century. Located in the southernmost part of the country, this area is still sparsely inhabited, though you will find a few populated places—like the colorful provincial city of Punta Arenas, which looks like it's about to be swept into the Strait of Magellan. Some unique wildlife, particularly colonies of elephant seals and penguins, call this breathtaking topography home. To the north is Parque Nacional Torres del Paine, the country's most magnificent natural wonder, and whose snow-covered peaks seem to rise vertically from the plains below. The vistas, such as the fantastic Avenue of the Glaciers, are breathtaking; along this stretch of the Beagle Channel, you can pass six tremendous glaciers all within a stone's throw of each other.Cruise SightsPunta Arenas. Founded a little more than 150 years ago, Punta Arenas (Sandy Point) was Chile's first permanent settlement in Patagonia. Plaza Muñoz Gamero, the central square, is surrounded by evidence of that early prosperity: buildings whose then-opulent brick exteriors recall a time when this was one of Chile's wealthiest cities. The newer houses here have colorful tin roofs, best appreciated when seen from a high vantage point such as the Mirador Cerro la Cruz. Although the city as a whole may not be particularly attractive, look for details: the pink-and-white house on a corner, the bay window full of potted plants, parking attendants wearing the regional blue and yellow colors, and schoolchildren in identical naval pea coats that remind you that the city's fate is tied to the sea.The Museo Naval y Marítimo extols Chile's high-seas prowess, particularly concerning Antarctica. Its exhibits are worth a visit for anyone with an interest in ships and sailing, merchant and military alike. Part of the second floor is designed like the interior of a ship, including a map and radio room. Pedro Montt 989. Admission charged.Housed in what was once the mansion of the powerful Braun-Menéndez family, the Museo Regional de Magallanes is an intriguing glimpse into the daily life of a wealthy provincial family at the beginning of the 20th century. Lavish Carrara marble hearths, English bath fixtures, and cordovan leather walls are among the original accoutrements. The museum also has an excellent group of displays depicting Punta Arenas's past, from the first European contact to the town's decline after the opening of the Panama Canal. The museum is half a block north of the main square. Magallanes 949. Admission charged.The resplendent 1895 Palacio Sara Braun is a national landmark and an architectural showpiece of southern Patagonia. Designed by a French architect, the house was built from materials and by craftsmen imported from Europe during the four years of construction. The city's central plaza and surrounding buildings soon followed, ushering in the region's golden era. Noteworthy are the lavish bedrooms, magnificent parquet floors, marble fireplaces, and hand-painted ceilings. Don't miss the portraits of Braun and her husband José Nogueira in the music room. Afterwards, head to the cellar for a drink or snack in the warm public tavern (a good portion of the mansion is leased to a hotel). Plaza Muñoz Gamero 716. Admission charged.Commonly referred to simply as "El Salesiano," the Museo Salesiano de Maggiorino Borgatello is operated by Italian missionaries whose order arrived in Punta Arenas in the 19th century. The Salesians, most of whom spoke no Spanish, proved to be daring explorers. Traveling throughout the region, they collected the artifacts made by indigenous tribes that are currently on display. Av. Bulnes 398. Admission charged.Isla Magdalena. Punta Arenas is the launching point for a boat trip to the Isla Magdalena to see the more than 100,000 Magellanic penguins at the Monumento Natural Los Pingúinos. A single trail, marked off by rope, is accessible to humans. The boat trip to the island, in the middle of the Estrecho de Magallanes, takes about two hours. Make sure to bring along warm clothing, even in summer; the island can be chilly, particularly if a breeze is blowing across the water.Parque Nacional Torres del Paine. Some 12 million years ago, lava flows pushed up through the thick sedimentary crust that covered the southwestern coast of South America, cooling to form a granite mass. Glaciers then swept through the region, grinding away all but the ash-gray spires that rise over the landscape of one of the world's most beautiful natural phenomena, now the Parque Nacional Torres del Paine (established in 1959). Snow formations dazzle along every turn of road, and the sunset views are spectacular.Among the 2,420-square-km (934-square-mi) park's most beautiful attractions are its lakes of turquoise, aquamarine, and emerald green waters. Another draw is its unusual wildlife. Creatures like the guanaco (a woollier version of the llama) and the ñandú (resembling a small ostrich) abound. They are used to visitors and don't seem to be bothered by the proximity of automobile traffic and the snapping of cameras. Predators, like the gray fox, make less frequent appearances. You may also spot the dramatic aerobatics of a falcon and the graceful soaring of the endangered condor. The beautiful puma is especially elusive, but sightings have become more common. Admission charged.Pingúinera de Seno Otway. The road to this penguin sanctuary begins 30 km (18 mi) north of Punta Arenas. Magellanic penguins, which live up to 20 years in the wild, return to their birthplace here every year to mate with the same partner. For about 2,000 penguin couples—no single penguins make the trip—home is this desolate and windswept land off the Otway Sound. In late September, the penguins begin to arrive from the southern coast of Brazil and the Falkland Islands. They mate and lay their eggs in early October, and brood their eggs in November. Offspring hatch between mid-November and early December. If you're lucky, you may catch sight of one of the downy gray chicks that stick their heads out of the burrows when their parents return to feed them. Otherwise you might see scores of the ungainly adult penguins waddling to the ocean from their nesting burrows. They swim for food every eight hours and dive up to 100 feet deep. The penguins depart from the sound in late March. Note that the sanctuary is a 1-km (1/2-mi) walk from the parking lot. It gets chilly, so bring a windbreaker. Admission charged.Reserva Nacional Laguna Parillar. This 47,000-acre reserve lies west of Puerto Hambre, a tranquil fishing village, and is centered around a shimmering lake in a valley flanked by hills. It's a great place for a picnic, and there are a number of well-marked paths that offer sweeping vistas over the Estrecho de Magallanes. About 2 km (1 mi) west of Puerto Hambre is a small white monolith that marks the geographical center of Chile, the midway point between Chile's northern port Arica and the South Pole.Cruise ShoppingWool may no longer be king of the economy, but vast flocks of sheep still yield a high-quality product that is woven into the clothing here. Leather products are also common, but the prices are not necessarily low. About 3 km (2 mi) north of Punta Arenas is the Zona Franca (Av. Bulnes). This duty-free zone is where people from all around the region come for low-priced electronics and other consumer items.

Day 9 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 11 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 12 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 13 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 15 Port Stanley, Falkland Islands (Malvinas)

Tiny Stanley, capital of the Falklands, seems in many ways like a British village fallen out of the sky. Many homes are painted in bright colours, adding visual appeal to this distant outpost. Not far offshore, the wreck of the Lady Elizabeth, is one of the many vessels remaining as a silent testimonial to the region's frequent harsh weather conditions.The islands, also known by their Spanish name of Islas Malvinas, are home to arguably more tuxedo-clad inhabitants of the penguin variety than human residents. Various species, such as Gentoo, Magellanic and the more elusive King penguins, either live here permanently or use the Falklands as a stopover on their migration route. Darwin found the islands' flora and fauna fascinating - no doubt you will, too.

Day 18 Puerto Madryn, Argentina

Approaching from Ruta 3, it's hard to believe that the horizon line of buildings perched just beyond the windswept dunes and badlands is the most successful of all coastal Patagonia settlements. But once you get past the outskirts of town and onto the wide coastal road known as the Rambla, the picture begins to change. Ranged along the clear and tranquil Golfo Nuevo are restaurants, cafés, dive shops, and hotels, all busy—but not yet overcrowded—with tourists from around the world.Puerto Madryn is more a base for visiting nearby wildlife-watching sites like Península Valdés and Punta Tombo than a destination in its own right. The town's architecture is unremarkable, and beyond a walk along the coast there isn't much to do. Indeed, even the few museums serve mainly to introduce you to the fauna you'll see elsewhere. The exception is the beginning of whale season (May through July), when the huge animals cavort right in the bay before heading north—you can even walk out alongside them on the pier. During these months it's worth the extra expense for a room with a sea view.The many tour agencies and rental-car companies here make excursion planning easy. Aim to spend most of your time here on one- or two-day trips exploring the surroundings. Note that competition is fierce between tourism operators in destinations such as Puerto Madryn and Puerto Pirámides on Península Valdés. Take information that tour operators and even the tourism office give you about these with a grain of salt: they often exaggerate Madryn's virtues and other areas' flaws.

Day 21 Punta del Este, Uruguay

Often likened to the Hamptons or St-Tropez, Punta del Este is a flashy destination where parties run nonstop in peak season. But it is also a destination that draws a range of beachgoers to its shores, from summering families to the celebrity jet-set. There's a bustling city on the beach downtown, as well as quiet countryside populated solely with upscale ranches called chacras or estancias, and creative, buzzing hamlets like La Barra and José Ignacio. Though it's pricey and at times a logistical challenge to get around, everyone finds something about Punta to love.The resort takes its name from the "east point" marking the division of the Río de la Plata on the west from the Atlantic Ocean to the east. It also lends its name to the broader region encompassing the nearby communities of Punta Ballena and La Barra de Maldonado. These days even José Ignacio, some 20 miles away, is grouped in. It's usually a given that Argentina's upper class spends at least part of the summer in Punta, soaking in the ample rays.

Day 22 Montevideo, Uruguay

Uruguay's capital city hugs the eastern bank of the Río de la Plata. A massive coastal promenade (malecón) that passes fine beaches, restaurants, and numerous parks recalls the sunny sophistications of the Mediterranean and is always dotted with Montevideans strolling, exercising, and lounging along the water. Montevideo has its share of glitzy shopping avenues and modern office buildings, balanced with its historic old city and sumptuous colonial architecture, as well as numerous leafy plazas and parks. It is hard not to draw comparisons to its sister city Buenos Aires across the river, and indeed Montevideo strikes many as a calmer, more manageable incarnation of Argentina's capital.When the weather's good, La Rambla, a 22-km (14-mile) waterfront avenue that links the Old City with the eastern suburbs and changes names about a dozen times, gets packed with fishermen, ice-cream vendors, and joggers. Around sunset, volleyball and soccer games wind down as couples begin to appear for evening strolls. Polls consistently rate Montevideo as having the highest quality of life of any city in Latin America. After one visit here, especially on a lovely summer evening, you probably will agree.

Day 23 Buenos Aires, Argentina

Glamorous and gritty, Buenos Aires is two cities in one. What makes Argentina's capital so fascinating is its dual heritage—part European, part Latin American. Plaza de Mayo resembles a grand square in Madrid, and the ornate Teatro Colón would not be out of place in Vienna. But you'll know you're in South America by the leather shoes for sale on cobbled streets and impromptu parades of triumphant soccer fans. Limited-production wines, juicy steaks, and ice cream in countless flavors are among the old-world imports the city has perfected.