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  • R. do Carmo 87-A, 1200-093 Lisboa, Portugal
    This small little wonder of a shop is located at 87 Rua do Carmo, the most fashionable street in Lisbon after the superseding Rua Garret. It is the last shop in the whole of Portugal, which is exclusively dedicated to the bespoke hand manufacture of leather gloves. The cream of the Lisbon society has been its avid clientele since 1925, procuring high quality leather tailor made gloves for those days when the sunshine is not enough to warm the hands. At about 50€ per pair, depending on the model and leather, you do not have to go to Italy to get a product of this tremendous quality. A woman from Chicago once told me that she had visited Lisbon ten years ago, where she had the opportunity to purchase a single pair. She was so impressed and the gloves had left such a good memory that she was here to get three or four more pairs in case she did not have the opportunity to come back to Lisbon for another ten years.
  • R. de Santa Cruz do Castelo, 1100-129 Lisboa, Portugal
    The Castelo de São Jorge, is one of the Alfama neighborhood’s most historically significant monuments. Plan a visit late in the afternoon so that you can explore every nook and cranny and learn about the castle’s abundant history. Stay for golden hour so that you can capture the light as it dances on the castle walls, and later to watch the sunset dip below the horizon.
  • Praça do Império 1400-206 Lisboa, 1400-206 Lisboa, Portugal
    Jerónimos Monastery, also known as the Hieronymites Monastery, or Mosteiro dos Jerónimos in Portuguese, is a UNESCO World Heritage Site in Lisbon. This stunning building took 100 years to build and it’s no wonder once you experience the level of detail for yourself. I could have spent an entire day there, with my camera, photographing the stunning architecture. The archways surrounding the inner courtyard look like something from a fairy tale.
  • Rua Senhora Saúde 6B, 1100-390 Lisboa, Portugal
    The city’s iconic wood-paneled Tram 28 rambles along a 4.3-mile route from Campo de Ourique to Praça Martim Moniz, navigating tight turns and steep inclines as it passes some of Lisbon’s most endearing attractions. Originally commissioned in the 1930s, these classic Remodelado trams were in fact enlisted for their ability to handle Lisbon’s hilly terrain. They can get painfully crowded—wait times can be outrageous in the high season—so catch an early ride (5:40 a.m. most weekdays, or 6:45 a.m. on Sundays) for unobstructed views of hilltop neighborhoods like Graça and the Alfama.
  • Av. da Liberdade 138-142, 1250-001 Lisboa, Portugal
    On Liberdade Avenue, amid famous designer stores, sits this five-star hotel. Each room is decorated in white and black with Victorian-inspired details. Enjoy one of the many sunny days in Lisbon, sitting outside in the terrace.
  • The Moorish Castle is strategically located on one of the top hills of Sintra to defend both the local territory and the maritime access to the city of Lisbon. The castle was built around the 10th century by the Muslim populations that occupied the Iberian peninsula. The castle acted as a control tower for the Atlantic coast and the land to the north, mostly serving as an outpost for the city of Lisbon. The castle’s Muslim rule ended in 1147 when King Afonso Henrique conquered Lisbon. In 1995, UNESCO listed Sintra hills as a Cultural Landscape, World Heritage, including the Moorish Castle. Highly recommended to climb and walk along the walls of the castle, carved out of the rock, to have a panoramic view over Sintra and its castles and palaces.
  • R. das Salgadeiras 5, 1200-169 Lisboa, Portugal
    With two shops very well located in two of the most visited neighborhoods, one at Chiado and the other at Bairro Alto, Bairro Arte sells crafts and design pieces created by young artists. Many of the pieces are connected to Lisbon in some way, for example a painting of Tram 28. But Bairro Arte is also a gallery, presenting contemporary art exhibitions, with paintings, photography, and sculptures that are sold at reasonable prices.
  • R. Garrett 50, 1200-203 Lisboa, Portugal
    This store was originally for Ouriversaria Alianca, an early 20th century jewelry carrier for Portuguese art. Today, the store has changed the brand and belongs to Tous brand, but the Art Deco interior design is still so dominant. The store has a well-kept secret; a fabulous back room, where you can see more jewelry. Located in one of the main shopping streets in Lisbon, Rua Garrett.
  • R. 1º de Dezembro 125, 1249-970 Lisboa, Portugal
    The Rossio railway station was designed between 1886 and 1887 by Portuguese architect José Luís Monteiro. It makes connections with the village of Sintra, and the 2,600-meter tunnel was excavated under the city. It is considered one of 19th-century Portugal’s most important works of engineering. It has a beautiful Neo-Manueline façade, where two intertwined horseshoe portals stand at the entrance, a clock sits in a small turret, and the sculptural decoration is abundant. Inside you can now find a Starbucks, Lisbon Destination Hostel, and a souvenir shop.
  • Jardim Teófilo de Braga, (em frente ao nº 26 da rua do 4 de Infantaria), 1350-266 Lisboa, Portugal
    A residential neighborhood with traditional commerce, and considered to be the most peaceful in Lisbon, this neighborhood brings together the best of life conditions to those who call this home. Taste a chocolate cake at the pastry shop which sells “The Best Chocolate Cake in the World” (Rua Coelho da Rocha, 99, next to the market). Then walk off your calories by visiting Santo Condestável’s Church, an emblematic monument which was designed by Vasco Regaleira, the architect of the “new churches.”
  • Pena, 1150 Lisbon, Portugal
    There are so many places to visit in this neighborhood, but I don’t see a lot of tourists strolling here, maybe because it’s located in one of the seven hills, Santana. But this is a neighborhood with more than 400 years of history, so if you’re not into climbing those steps, just use Lavra’s lift, it will take just few minutes. Stroll around Casco Velho (meaning “old town”), visit the ancient parish of Campo Santana that in old times served as a bullring and flea market, and skip the tourist trap of restaurants next to Coliseu dos Recreios. Here in Pena neighborhood, you will be among the locals, tasting Portuguese food and enjoying views over Lisbon.
  • Rua do Paraíso 15B, 1100-395 Lisboa, Portugal
    This Lisbon restaurant, more than 30 years old, is known for its creative take on Portuguese gastronomic traditions. An extensive wine list represents the many regions of the country offering opportunities to explore by simply ordering a glass. Other bonuses: the restaurant’s glorious views over the river and its location, behind the Santa Apolónia train station, less than five minutes from the National Pantheon.
  • Largo do Chafariz de Dentro, 1100-139 Lisboa, Portugal
    This square is located in the oldest and one of the most typical neighborhoods in Lisbon. Yes, typical houses, old cafes, and grocery shops can still be found here. If you hear hollering out a window, don’t worry, probably it’s just someone calling a neighbor, it isn’t a fire; it’s just how things are done in the daily life of the Alfama locals. If you’d like to know more about Fado (Portuguese folk singing), visit Fado Museum. If you feel like trying to sing it, just choose one of the narrow streets and look for an old tavern. In these taverns, after some cups of aguardiente (Portuguese brandy), everyone sings Fado—usually Fado Vadio (sung by non professionals) or Desgarrada (between two singers, improvising verses that tell a fun story). Don’t expect great voices, as probably everybody is out of tune!
  • R. do Vigário, 1100-502 Lisboa, Portugal
    To get to know the neighborhood and its daily life, nothing beats a stroll through Alfama’s streets. It is the oldest and one of the most typical neighborhoods in Lisbon. Here you might see two women chatting at the window (well, screaming) while hanging the laundry; people sitting outside on small wooden benches or the entrance steps to old houses; and, of course, people listening to fado. The sounds of fado can come from a fado restaurant or from an old tavern (here fado is called Fado Vadio since it is sung by nonprofessionals after drinking aguardiente). On the nights of June 12 and 13, Alfama celebrates Santos Populares, when the streets are adorned with colorful little flags, the air is aromatic with smoke and smell of sardines, the beer is flowing, and music is everywhere.
  • 16 Praça da Figueira
    Located in downtown facing the square Praça da Figueira, this 18th-century building, with a view of São Jorge’s castle, was recently restored and has become a hotel. The name is that of the square, Figueira, which in Portuguese means Fig Tree. This square once housed a market (many years ago) and was surrounded by fig trees. So you will find green and brown are the predominant colors, and the fig is the main element of the décor, designed by Nini Andrade Silva. The hotel’s restaurant, Honra (Honor), is dedicated to Portuguese cuisine. (Chef Olivier has three other restaurants in Lisbon: Olivier Avenida, Yakuza, and Guilty.)