If you're bound for Portugal's small but sprightly Estoril Jazz Festival, staged inside Europe's largest casino from May 11 to 20, then one of the continent's most compact capital cities is but a half-hour away by coastal highway or commuter train. Starting and ending at the rail terminal of Cais do Sodré, here's a half-day tour of undulating hilltops and tram-traveled boulevards to take in the instantly intimate essence of Lisbon a stately white city, a scholars' lair, a seafaring hub.
HOUR 1: After exiting the terminal, take the steep, cobbled climb toward classy Chiado and get a feel for Lisbon's burgeoning bohemia: organic bakeries and design stores ply their trade alongside more traditional antiquarians and sellers of the famous azulejos (blue-tinged tiles). Refresh in the stately Largo do Camões at one of the characteristic kiosks that have recently been lovingly refurbished with new paint and stocked with nostalgic sodas and pastry treats. Within a few blocks are the youth hangouts of the Bairro Alto, as well as two of Lisbon's most emblematic haunts the overly touristy Café a Brasileira (cafe-abrasileira.com), featuring the eternal bronze statue of famed local poet Fernando Pessoa, and the Solar of the Instituto dos Vinhos do Douro e Porto (www.ivdp.pt), with stuffy waiters and a hushed atmosphere perfect for savoring the best vintages, both tawny and white. Catch the No. 28 tram at Camões (a must-do, even if crammed with visitors delighting in this exceptionally atmospheric ride) and enjoy the curving switchbacks and glimpses of the medieval until you hop off at Graça. Follow the side of this cathedral's massive ramparts toward the miradouro (viewing point) for a magnificent vista of Lisbon's splendor far better than any on Google Earth.
HOUR 2: Strolling back downhill along the tram route, ubiquitous bakeries offer pastéis de nata (Portugal's luscious egg tarts), queijada cakes with cinnamon, and cavity-causing meringues in pink and white. On Tuesdays and Saturdays, the sprawling area behind the enormous São Vicente church holds the Feira da Ladra an old-fashioned flea market featuring everything from family heirlooms to hippie rags to vintage porn around a beautifully restored market newly opened as a burgeoning center for Portugal's undercelebrated culinary arts. Backtracking toward Centro, plunge into the laundry-draped alleys of the Mouraria, one of the poorer and least trammeled enclaves that offers a dazzling concentration of fanciful facades and grubbiness. If hungry, join the locals at Zé da Mouraria (Rua João do Outeiro 24), a neighborhood kitchen, for hearty bacalhau, veal roasts and squid in giant casserole pots over which the brawny Zé himself labors.
HOUR 3: If not too slowed by vinho verde, the young, fizzy Portuguese wine consumed like water, continue past the blocky medieval turrets of the cathedral, stopping for Austrian desserts and a good galão (Portugal's latte in a glass) at the comfortable, hippie-like Pois (poiscafe.com). Down to the waterfront, survey the wildly baroque-tiled facades on the way south to the little-known Museu do Fado (museudofado.pt). Through highly imaginative and loving interactive displays, get a quick hit of Lisbon balladeering and note that the sounds presented, and offered for sale in the extensive gift shop, are far more heartfelt than those in the tawdry fado dinner houses. Next, hop in a cab to explore the many new outstations that are reclaiming the warehouses of the Rio Tejo waterfront and turning them into trendy cultural centers. Best among these is the Museu do Oriente (museudooriente.pt), a glitzy showcase of Lisbon's other great heritage: the Portuguese colonies founded by its bold navigators. It's the next best thing to a trip to Goa or Macau.
HOUR 4: By now you're within a container ship or two of LX Factory (lxfactory.com), the onetime premises of a textile company that was transformed into an arts center in 2008. Frequent performances and exhibitions can be found there, along with Ler Devagar (Read Slowly), a bookstore outfitted with elaborate automatons and windup toys. If you still have energy, Belém's Mosteiro dos Jerónimos, the city's iconic masterpiece of late-Gothic architecture, is 10 minutes north. A more offbeat finish to the day would be to catch a cross-river ferry back at the Cais do Sodré. Wander the abandoned piers and waterfront cafés of Cacilhas, a vantage point for all Lisbon's gleaming urban topography and the 25th of April Bridge, seen from the far side of the Tejo. Sunsets with superb wine and cheese are provided by a small restaurant-bar appropriately named Punto Final, tel: (351-21) 276 0743.