Alfama

Opened in the 1930's and virtually unchanged ever since, Conserveira de Lisboa (Lisbon Cannery), sells mainly brightly colored vintage tins of fish. Quirky as it is, its charm is undeniable, whatever your culinary proclivities may be.

From the cozy living room check-in, to its forty-two rooms with amazing views, every inch of the place is intimate and relaxing.

In the center of the city right by the Fiera de Ladra, Lisbon’s flea market, Santa Clara 1728 is a beautiful 18th-century palace that has been transformed into a quiet, romantic sanctuary. Reminiscent of a chic, upscale bed and breakfast, this hotel has six spacious suites and a dining room where the owners (a family who also calls the space home) host delicious dinners open to all guests. Limestone staircases, minimalist wooden furniture, and impressive artwork all complement the beauty of the building itself. Bonus: luxurious, heated bedroom floors, along with views of the Tagus River and National Pantheon.

Known for serving some of the best seafood in Lisbon, the brightly lit Cervejaria Ramiro is always bustling with foodies—local and foreign alike—clamoring to try the restaurant's famous clams in garlic sauce, grilled giant tiger shrimp, and percebes (goose barnacles), among a host of other amazing options. While it may seem like you won't have room to try anything but the seafood, save some for their prego, a Portuguese steak sandwich—it's said to be the best in the city. Note: unsurprisingly, this place is pretty popular, so if you want to avoid the line (it's first-come, first-served), it's best to try for an early dinner.

This is a wonderful, aptly named late-night spot where you can get your dose of Fado; it's the kind of comfortable local place where you can end a night with a good meal, a gorgeous set of songs, and a glass of brandy.

One of Portugal's most popular venues, Lux Frágil has remained a fixture of Lisbon nightlife since opening in 1998. Located near the waterfront, with three distinct but connected areas—a club, a bar, and a rooftop lounge—the interior is a sleek and fashionable setting for weekly events consisting of mostly house, techno, and disco music, presented by an impressive selection of well-known DJs. If you’re not a hardcore dancer, you can stick to the upstairs bar, which is a bit more laid back. Beware: As one of Lisbon’s most famous clubs, the line gets pretty long on the weekends, so it's best to arrive on the earlier side.

This legendary kitchen and gourmet shop is worth visiting for the facade alone—practically untouched since the store opened almost a hundred years ago, it features ornate, gold-painted signage and old-school merchandising windows. The shelves are filled with Portuguese products like cans of sardines and tuna, homemade jams and quinces, oils, wine, spirits, and crackers. It's an ideal place to pick up souvenirs.

Set on the city's tallest hill (where its Middle-Age inhabitants could best see incoming threats), São Jorge Castle was originally built by the Moors, before it was captured by the Christians who eventually ruled the city. Despite its dramatic history, today, the castle is one of the city's most relaxing and tranquil places—there are peacocks wandering around the grounds, and gorgeous views of the city from the defensive towers. Leave a little time to explore the camera obscura.

Alfama is one of Portugal's oldest districts, and since the hilly area is filled with sets of stairs and narrow alleys, it's best explored by foot (though the 1930's-style tram that makes up the only public transportation here is worth hopping on for fun). The neighborhood's never really been tony, and though younger generations have taken over several restaurants and storefronts, the original community is still very much intact thanks to generous rent control programs. There are several attractions worth exploring while you're here. Start with Castelo de São Jorge, the beautifully restored site of the Christians' 12th-century defeat of the Moors, where there are tons of lookouts with views of the sea and surrounding neighborhoods. Also visit the Church of St. Anthony, the birthplace of its namesake, the patron saint of lovers—newly married couples often leave flowers here in hopes of a happy marriage, and single people try to throw coins into his book for good luck finding a partner. Though it's not a must, it's fun to check out the Fado Museum, which memorializes a specific musical style born in Alfama: a solemn, dramatic singing and guitar…