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While most of Lisbon’s historic core practically oozes old-world charm—colorful laundry on the lines, gossiping grandmas with their heads out the window—a few neighborhoods stand out as particularly pleasing.
Principe Real
Upscale but small scale, Principe Real is home to a number of the city’s moneyed creative types, including a lot of foreign residents. Its main street is lined with high-end independent boutiques and gourmet restaurants, including some from star chefs Henrique Sá Pessoa (Tapisco) and Kiko Martins (Cevicheria). The park in the center is one of the prettiest in town, and the views from the east side of the main street are impressive. The Vintage would be the hotel choice in this neighborhood.
Chiado
In New York terms, I would call Chiado the SoHo of Lisbon. There’s a mall and outposts of international brands, from H&M to Hermès, with a few high-end homegrown designers mixed in. It’s not very residential anymore, with most of the apartments used for short-term rentals, but it’s home to some of the city’s best boutique hotels and trendy restaurants, including most of celebrity chef José Avillez’s empire. There’s almost always live music in the main square, Praça Luís Camões, and The Bairro Alto Hotel would be my hotel pick.
Alfama
The city’s most historic district, and the one you’re most likely to see in postcards, is a warren or narrow streets, alleyways and staircases where even locals are lively to get lost. While there are a lot of short-term rentals, a lot of the longtime residents remain, adding to the charm. (Though if you want a beautiful hotel in the heart of the area, right along the water, stay at the Memmo Alfama.) The streets are lined with souvenir shops, traditional little restaurants and fado bars. Be warned that it can get crowded, particularly when there’s a ship at the cruise terminal.
Graça/Castelo
The historic Castelo neighborhood is centered on Castelo São Jorge, the castle that dominates that side of Lisbon’s skyline. Inside the castle walls, there are small streets filled with residential apartments, souvenir shops and a few restaurants, and of course the castle itself. Outside the walls, it spills into Graça, a newly lively neighborhood that retains its historic charm even as parts are gentrifying. A stay at the Palácio Belmonte will make you feel like royalty.
Santos
While a little bit off the tourist path, this neighborhood has become trendy in the past few years. Now it’s a destination for local hipsters, foreign residents and in-the-know tourists. (The Palácio Ramalhete would be the hotel I’d choose.) The cafés, restaurants and bars are increasingly international, but the vibe is still small scale and intimate. Word has it that Madonna lived here during some of her time in Lisbon.
