Overnight in Lisbon, Portugal’s lively capital, where winding streets lead to historic cathedrals and grand plazas. Sail roundtrip from Porto and cruise the Douro River Valley, the world’s oldest demarcated wine region and a UNESCO Site, where rural quintas line the hillsides. In Spain, visit Salamanca, home to one of Iberia’s oldest universities, before returning to Porto to enjoy its namesake wine, flavorful food and evenings of soulful fadó music.

Soak in the eclectic mix of Latin and European influences in the Argentine capital of Buenos Aires, the birthplace of tango. Visit historic Port Stanley on East Falkland Island, home to more than one million penguins, and explore the scenic surroundings of Ushuaia, the city at the “End of the World.” Sail through the Strait of Magellan, passing rugged mountain peaks and blue-tinted icebergs and experience Chile’s vibrant capital city, Santiago.