Lisbon

Fly into Lisbon Humberto Delgado Airport (10 minutes from the city center) and transfer to your hotel. Lisbon's first impression is the light — a particular Atlantic luminosity that turns the city's terracotta and azulejo tiles golden in the afternoon. Walk immediately to Alfama — the ancient Moorish neighborhood of steep winding lanes, laundry strung between windows, and a hilltop castle — for the city's most atmospheric introduction. The Portas do Sol miradouro (viewpoint) at dusk, looking over Alfama's terracotta rooftops to the Tagus, is the essential Lisbon moment. Dinner at a fado restaurant in Alfama.

Belém — 6km west of the city center at the point where the Tagus meets the Atlantic — is where Vasco da Gama's fleet departed for India in 1497 and where the Age of Exploration is memorialized in extraordinary Late Gothic Manueline architecture. The Mosteiro dos Jerónimos (Jerónimos Monastery) is the most ornate church in Portugal — a UNESCO World Heritage site with a cloister of such extraordinary carved stonework (ropes, armillary spheres, coral, exotic fauna from the newly discovered world) that it seems grown rather than carved. The Torre de Belém in the river is the most photographed building in Portugal. And around the corner: Pastéis de Belém, where the original recipe custard tart has been made since 1837.

Sintra — 40 minutes by train from Rossio station — is a UNESCO World Heritage cultural landscape of extraordinary Romantic palaces and gardens in the pine-covered Serra de Sintra mountains above the Atlantic. The Palácio Nacional da Pena (a wildly polychrome Romantic palace on the highest peak, built for Prince Ferdinand of Saxe-Coburg-Gotha in the 1840s) is the most extraordinary building in Portugal — a collision of Moorish, Gothic, Renaissance, and Manueline styles painted in terracotta and mustard yellow. The Quinta da Regaleira below the village has a 27-meter deep initiation well reached by a spiral staircase.

Chiado is Lisbon's most elegant neighborhood — bookshops (Livraria Bertrand, the world's oldest operating bookshop, 1732), cafe A Brasileira where Fernando Pessoa had his morning bica, and the Rua Garrett with its beautiful old shops. Bairro Alto — uphill from Chiado — is Lisbon's bohemian quarter, quiet by day and full of tiny tasca restaurants and wine bars by night. LX Factory in Alcântara is a 19th-century industrial complex converted into a weekend market and restaurant quarter — the Sunday market is one of Lisbon's great experiences.

Tram 28 — Lisbon's legendary yellow tram on its original 1930s route — grinds and squeals through Alfama, Graça, Mouraria, and Chiado on a circuit that takes in most of the city's hills and best neighborhoods. Ride it from Martim Moniz to Campo de Ourique and back. The miradouros (viewpoints) that punctuate the hilltops are Lisbon's social institutions — Miradouro da Graça (the locals' favorite), Miradouro de Santa Catarina (the sunset viewpoint in Bairro Alto), and Miradouro da Senhora do Monte (the highest viewpoint in the city) all have bars or kiosks and are filled with locals in the late afternoon.

The train from Cais do Sodré west along the Tagus estuary and then the Atlantic coast reaches Cascais in 40 minutes — a beautiful fishing village turned elegant resort town with a harbor, a palace, and a promenade along the cliff above the Atlantic. The Boca do Inferno (Mouth of Hell) — a chasm in the cliffs where the Atlantic surges into a tunnel and emerges in a violent explosion of spray — is 2km west of the town. Continue by taxi to Cabo da Roca, the westernmost point of continental Europe, where a lighthouse stands above 150m cliffs at the edge of the Atlantic, staring toward America.

Final pastel de nata and bica (espresso) at a Chiado cafe before your flight. Lisbon airport is 15 minutes from the city center.