Don't visit Lisbon because it's cheaper than Paris (though it is) or faster to reach than Rome (also true). From the steep, labyrinthine streets and shouting fishwives of the ancient Alfama district to the city's clacking yellow trolleys, from impressive monuments to the Age of Exploration to singers belting mournful fado ballads in supper clubs, Europe's westernmost capital has an Old World charm that's wholly its own. The country's troubled economy hasn't changed the fact that Lisbon has more than just tradition to sell it as a transatlantic escape, with an increasingly forward-looking food scene, high-bohemian bars and heaving international nightclubs that go until dawn. The hilly city (bring comfortable shoes) is a seven-hour direct flight from New York, and the Friday night redeye lands you at a perfect time to begin a whirlwind weekend adventure.  12 p.m. Check into a river-view room at the new LX Boutique Hotel (from about $230 per night, 12 Rua do Alecrim, lxboutiquehotel.pt), in the city's central Baixa district. Drop off your bags, then wander up Rua do Alecrim, past the string of antiquarian book shops just north of the hotel. If you've got a thing for beautiful old maps or flaking but weirdly attractive antique statues of Our Lady of Lourdes, you've just hit pay dirt.  1:15 p.m. Grab lunch at Cais do Chiado, an organic grocery and café a few doors north of the hotel (26M Rua do Alecrim, 21-343-1072). Afterwards, head up into Chiado, the city's toniest commercial district, with its cheery Belle Epoque cafés and mix of local and international boutiques. A Vida Portuguesa (11 Rua Anchieta, avidaportuguesa.com) specializes in re-issues of long-forgotten but surprisingly of-the-moment toys, housewares, toiletries and food products—canned fish will suddenly seem like a sophisticated souvenir. Luvaria Ulisses (87 Rua do Carmo, luvariaulisses.com), a sliver of a shop behind a pretty neoclassical façade, has been making and selling fine leather gloves since 1925; the Ana Salazar boutique next door (anasalazar.pt), from Portugal's best-known fashion designer, is a great place to find avant-garde women's wear that you won't see on anyone else back home.  4 p.m. Take the eccentric Santa Justa Lift (Rua de Santa Justa, near Luvaria Ulisses), a 135-foot, neo-Gothic outdoor elevator built in 1902 by an Eiffel acolyte. The lift actually goes to the penultimate level; the final leg of the climb, via one of the world's most beautiful corkscrew staircases, leads to an expensive café and fabulous views over the district. Exit from the catwalk ramp to the Convento do Carmo, a convent and church built between 1389 and 1423 and wrecked by the great earthquake of 1755. What remains is an open-air ruin: slowly crumbling stone walls and soaring, empty arches. There's a small but brilliant archaeological museum here (museuarqueologicodocarmo.pt), packed with historic statuary, pre-Columbian mummies (the long-haired Peruvian one looks a bit like Joan Rivers after a bender) and an Egyptian sarcophagus dating to around 700 B.C.  5 p.m. Walk a few minutes northeast to Praça de Dom Pedro IV, the city's main square (locals call it Rossio) and a prime hang for people-watching. You'll see South Asian laborers, Senegalese buskers, hipster skateboarders, pudgy German tourists and Portuguese country folk shuttling to and from the Estação Ferroviária do Rossio rail station at the edge of the square. Confeitaria Nacional (18B Praça da Figueira, confeitarianacional.com), a charming, two-story pastry shop that first opened in 1829, sells flaky, not-too-sweet pastel de nata custards. Jars of doce de abóbora (pumpkin jam, which tastes far better than it sounds) are stacked into tidy pyramids in the original glass display cases. Wash the goodies back with a $1.50 shot of cherry brandy from the Ginjinha do Rossio at the other end of the square (8 Largo de São Domingos). That'll put you in good form for a quick visit to the haunting Igreja de São Domingos across the street, site of the country's royal weddings until the early 1900s. Largely destroyed by fire in 1955, it has been partially restored. Black-clad ladies pray their rosaries by votive candlelight as pigeons flap noisily overhead. Many of the old stone pillars still glow black from the fire.  6:30 p.m. Walk or taxi up to the Miradouro de São Pedro de Alcântara (Rua de São Pedro de Alcântara), a formal but charming public garden, for a quick but glorious view across the city, then hop the Elevador da Glória (Praça dos Restauradores), a funicular built in the late 1800s, down to Rua São Pedro de Alcântara, a cobblestone street punctuated with design stores and art galleries, which leads back south to the hotel. You might want to take a nap.  9 p.m. Cab it a few minutes west to A Travessa (12 Travessa do Convento das Bernardas, atravessa.com), a warm, welcoming and slightly idiosyncratic restaurant (the bartender shuttles patrons home himself in a red Volkswagen van) housed in a 17th-century convent. Start with a glass of white port and order a main course; a succession of small, sublime daily appetizers—from creamy scrambled eggs with wild mushrooms to clean-tasting carpaccio of salt cod, to a slice of grilled, gorgeously fatty wild boar—will begin to arrive within seconds. The wine list is excellent, stacked with (more or less) affordable domestic treasures from Dao, Barraida and the Douro.  11 p.m. The city's young and fashionable start the night off (yes, at 11) in Bairro Alto, the bar and fashion district. Tiny Maria Caxuxa bar (12 Rua da Barroca), with its high-flea market décor and beautiful clientele, is one of the most popular, though to be honest, it doesn't particularly matter which place you pick; most people buy their drinks inside then join the open-air party in the streets.  1:30 a.m. In a city that's famed for its nightlife, the 12-year-old Lux-Frágil (42 Rua Gustavo Matos Sequeira, luxfragil.com) is still considered the go-to after-hours hangout. Part owned by John Malkovich, the two-story lounge, disco and concert space doesn't really get going until about 2 a.m.; the party carries through until the sun rises over the Tejo, which you can watch from the rooftop. Don't miss artist Joana Vasconcelos's enormous chandelier, it's made with tampons—25,000 of them.  11 a.m. After sleeping in, take tram No. 15 from the Cais do Sodré, just south of the hotel, to Belém, Lisbon's prime cultural district and the place from which Vasco da Gama sailed for India in 1497. Though the opulent gardens, museums and finely detailed late Gothic architecture here can absorb days of wandering, start with a stroll around the harbor. The striking 170-foot concrete monument that's shaped like a ship's prow was built in 1960 to celebrate 33 of Portugal's most important men from the Age of Exploration. Jutting into the river to the west is the 16th-century Tower of Belem, a spectacular military fortification, and beyond that, the Atlantic Ocean. The Golden Gate-esque bridge to the east is the Ponte 25 de Abril (after the date of Portugal's "Carnation Revolution").  12 p.m. Have a restorative lunch in the Clube Naval de Lisboa (Doca de Belém), at one of its second-story seafood spots overlooking the Tejo River.  1:30 p.m. Walk to the Mosteiro dos Jerónimos (Praça do Império, mosteirojeronimos.pt), the enormous monastery complex started in 1502 to celebrate Vasco da Gama's first successful voyage to India (his tomb is just inside). Its construction was funded largely with the loot the country's mariners brought back, and it's considered a masterpiece of Portugal's lavish Manueline style of architecture.  2:30 p.m. The Museu Nacional dos Coches (Praça Afonso de Albuquerque, museudoscoches.pt), or coach museum, is somewhat less grand but a hell of a lot more fun, particularly for auto buffs. It houses one of the planet's greatest collections of royal carriages. Most of them, like the Italian buggies from 1716 that once belonged to Pope Clement XI, are in mint condition and totally pimped—the triumphal red-silk-and-wood embassy coach features gilt-covered statues representing Abundance, Heroism, Immortality and Fame (Fame's the bare-breasted one, we're guessing), plus cherubs, slaves and a winged dragon smashing a Muslim crescent. They're easily the most tricked-out rides that any of us will ever see.  4 p.m. The Museu Colecção Berardo (Praça do Império, museuberardo.pt) a few blocks to the west provides a somewhat more modern view of Portugal. The four-year-old museum showcases the collection of entrepreneur José Manuel Rodrigues Berardo, and includes works by 20th-century Portuguese artists as well as canvases from Pablo Picasso, Francis Bacon and Salvador Dalí.  7 p.m. Stop in at the Chafariz do Vinho (Rua da Mãe d'Água at Praça da Alegria, chafarizdovinho.com), near Rossio. It's one of the city's best wine bars, set in a 18th-century stone reservoir that's linked to the city's aqueducts; splurge on the flight of 10-, 20-, 30- and 40-year old ports for about $42.  8:30 p.m. Cab out to Alfama, a quiet, hilly, twisty riverside district that's the oldest neighborhood in Lisbon, for dinner and mournful but beautiful live music at the Clube de Fado (the roughly $17 cover includes snacks, 94 Rua de São João da Praça, clube-de-fado.com).  9:30 a.m. You're going to need some provisions—like pata negra ham, figs, chocolate, bottled water and vintage port. Stop at Manuel Tavares near the Rossio station (1 Rua da Betesga, manueltavares.com), a deli and wine shop with a lust-worthy cellar, founded in 1860. Grab a few bags of roasted chestnuts outside the station, too. Meet a guide from bikeiberia, a local cycling tour company, at the station (bikeiberia.com) and take the 40-minute commuter train to Sintra to tour the spectacular Unesco-protected trio of mountaintop castles (plus smaller, no less impressive ones in the village below) that look out over Lisbon and the Atlantic coast. Though there's about 600 feet of climbing, afterwards the ride is mostly downhill, 17 miles from the 19th-century Romanticist gem Pena National Palace, to Guincho beach, the long, surf-pounded expanse of sand where the opening shots of "On Her Majesty's Secret Service" were filmed. Watch out for the riptides if you swim.  6:30 p.m. Arrive back in Lisbon in time to catch a late flight home.
The ultimate three-day itinerary for Portugal's capital, packed with art, pastries, castles, trolleys, fado music and late-night revelry.