Chile Cruise from San Antonio to Ushuaia — 19 Days

San Antonio, Chile

San Antonio is Chile’s largest commercial port, a working coastal city with a distinctly local rhythm. Its appeal extends beyond the docks: Santiago lies about 110 kilometres inland. Valparaíso is north, while the Casablanca Valley’s wineries offer a rewarding excursion nearby. Begin at the fish market and waterfront, or venture to Santiago, Valparaíso and Casablanca’s vineyards.

At Sea (At Sea)

Puerto Montt, Chile

Puerto Montt is Chile’s working gateway to the Lake District, where the Andes rise above deep blue water. At the waterfront, fish stalls and seafood kitchens make the city’s maritime life easy to taste. Browse Angelmó market for smoked salmon, shellfish and local crafts, then look north toward the snow-covered cone of Osorno. Beyond town, lakes, forests and Chiloé’s distinctive island culture reward travelers who venture farther.

• Coastal Cruising (Coastal Cruising)

Chilean Fjords, Chile

South of Puerto Montt, Chile’s fjords form a maze of islands, channels and snowbound peaks. Glaciers descend from the Southern Patagonian Ice Field, while temperate rainforest reaches the water’s edge. Watch for dolphins and seabirds from deck; shore landings, where offered, reveal remote coastlines at close range. These are working waterways as well as wild scenery, best appreciated slowly, with camera ready and plans flexible.

Caleta Tortel, Chile

At the mouth of the Baker River, Caleta Tortel stands between Patagonia’s Northern and Southern Ice Fields. Forested slopes meet Pacific channels, while cypress boardwalks take the place of roads. Raised walkways link homes, piers and viewpoints, bringing visitors close to this remote settlement. Come for quiet water, local boats and a rare glimpse of life along Chile’s Carretera Austral.

• At Sea (At Sea)

Chilean Fjords, Chile

South of Puerto Montt, Chile’s fjords form a maze of islands, channels and snowbound peaks. Glaciers descend from the Southern Patagonian Ice Field, while temperate rainforest reaches the water’s edge. Watch for dolphins and seabirds from deck; shore landings, where offered, reveal remote coastlines at close range. These are working waterways as well as wild scenery, best appreciated slowly, with camera ready and plans flexible.

• At Sea (At Sea)

Strait of Magellan, Chile

The Strait of Magellan is not merely a passage between oceans; it is a frontier of wind, water and history. In 1520, Ferdinand Magellan’s expedition became the first European fleet to navigate this route between the Atlantic and Pacific. Today, a voyage through Chile’s intricate channels reveals snow-capped peaks, wooded shores and the stark landscape of Tierra del Fuego. Watch the weather shift, and understand why this waterway once commanded the world’s attention.

Punta Arenas, Chile

At the edge of the Strait of Magellan, Punta Arenas feels like a city built for crossing oceans. Its broad avenues and ornate mansions reflect the fortunes of sheep farming and trade. The Maggiorino Borgatello Museum traces Patagonia’s natural and human history. Climb Cerro de la Cruz for views across the harbor and rooftops. From here, boats reach Magdalena Island, home to thousands of Magellanic penguins.

At Sea (At Sea)

Coastal Cruising (Coastal Cruising)

At Sea (At Sea)

Ushuaia, Argentina

Ushuaia sits between the Beagle Channel and the snow-streaked Martial Mountains, at Argentina’s far southern edge. Its harbor has long served as a gateway to Antarctica, while the town itself rewards a slower look. Ride the End of the World Train into Tierra del Fuego National Park, or tour the former prison museum. Here, wild landscapes begin just beyond the last streets.