Lisbon, Portugal

The number 28 tram climbs through Alfama's steep, narrow streets past centuries-old tiled facades — it's Lisbon's signature ride, though it's worth boarding early in the morning or simply walking the route instead, since midday crowds mean a long wait and a standing-room-only car.

Belém, a short tram or bus ride from the center, pairs the Belém Tower and Jerónimos Monastery with a stop at the original Pastéis de Belém bakery for the custard tart the whole country is named after by reputation. Sintra, about forty minutes by train, adds a genuinely different day trip: fairy-tale palaces built into forested hills, distinct from anything on the Algarve coast we already book for beach trips.

TAP Air Portugal flies nonstop from most East Coast gateways in about seven hours. April through June and September through October bring comfortable temperatures; July and August turn Lisbon genuinely hot and considerably more crowded.

Built across seven hills, Lisbon rewards comfortable shoes and use of its historic tram network (Tram 28 in particular) to cover the steeper climbs between neighborhoods. The Belém district, a short ride from the center, holds the Jerónimos Monastery and Belém Tower from Portugal's Age of Discovery, along with the original pastéis de nata custard tart bakery the pastry is named after.

Four nights covers the city's hills and the Belém district, often extended with a day trip to Sintra's palaces. It suits travelers who enjoy walking and don't mind hills, and comfortable shoes matter more in Lisbon than in most flat European capitals.

Getting there: About 7h nonstop from most East Coast gateways (TAP Air Portugal). We check the realistic routing options for a trip like this and help time it around April to June, or September to October rather than leaving it to chance.

Lisbon is built across seven hills along the Tagus River, a geography that produced the city's iconic yellow trams — particularly Tram 28, still a functioning public transit line rather than a tourist reproduction — specifically engineered to handle the steep, narrow streets that regular buses can't navigate. The city was devastated by a massive earthquake, tsunami and fire in 1755 that killed tens of thousands and leveled much of the historic core; the rebuilt Baixa district that followed was one of the earliest examples of seismic-resistant urban planning anywhere in the world, designed under the Marquis of Pombal with wooden lattice framing (the 'gaiola pombalina') built into building foundations specifically to flex rather than collapse in future quakes. Fado, Portugal's melancholic traditional music genre centered on themes of longing and fate (saudade), developed in Lisbon's working-class Alfama and Mouraria neighborhoods in the early 1800s and remains performed live in small, intimate tascas across those same neighborhoods today, UNESCO-recognized as intangible cultural heritage. Portuguese cuisine in Lisbon runs on bacalhau (dried, salted cod), reportedly prepared in over 365 different traditional recipes, and on pastéis de nata, the custard tart whose original recipe is still a closely guarded secret at Pastéis de Belém, the bakery that's produced it since 1837.