Lisbon is the colorful capital of Portugal and has much to offer. But, this guide will also cover the Belém district of Lisbon, Cascais, and Sintra since they are just too close not to explore. The sites are spread out in Lisbon, which is why you have many options for lodging and any location is close to something you'll want to see.
The narrow hilly streets of Lisbon should be its national treasure. Apparently every night I miss out on a party, as every morning sanitation workers are hosing down plastic cups and trash to the bottom of the hill for pickup. Almost every turn provides a great view. Some alleys trail off at angles that will challenge even the best navigator. And unexpected treasures await at every turn. Trams and funiculars are available to help you deal with the steep roads. There are unique lifts, like the industrial age Elevador de Santa Justa in the Baixa district that offers a view and nothing more, and practical lifts. Tram 28 is the most famous tram, and you just have to ride it because it winds its way through tight alleys and provides some of the best people watching anywhere. Beware of pickpockets. It stops at a lot of attractions, such as Estrela Basilica, the huge domed church. Personally, I prefer the exterior of this church and the interior of the Se Cathedral, which is about 2 miles away at another tram stop.
The best part about Lisbon is letting youself get lost in the winding narrow alleys. I love exploring the Alfama district for this reason, not to mention it's the oldest part of the city. Small eateries are frequent and they don't disappoint, offering delicious and inexpensive meals such as chargrilled squid. While you're in this area, I recommend visiting St. George Castle. First established in 200BC, it was completely destroyed by an earthquake in the 1700s and finally restored in the 1940s. Enjoy stunning views from atop the walls, cool off in the garden, and learn about history from the exhibits. As you continue finding your way out of the maze of Alfama, you'll undoubtedly run across hundreds of those famous blue tiles. Nearby is Comercial Plaza (Praca do Comercio), which I think is the best plaza in Lisbon. It is surrounded by great architecture and is along the waterfront. To the west is a delicious food market - the Mercado da Ribeira. The bottom level is the produce market and the upper level is a place to get a local snack and some wine.
At this point you can either head to Bairro Alto or see museums. If you are interested in museums, the Gulbenkian Museum in north Lisbon is worth a visit to see the vast ancient art collections. In east Lisbon is the National Tile Museum, which gives a great history on tile making from the Moorish times. Otherwise, enjoy Bairro Alto, which is packed with cafes, fine dining, and nightlife options. In this area, you can stumble upon a number of humble restaurants where you will be given an outdoor seat and be presented with various fresh fish and meats to pick out for your meal. Prepared tableside, absolutely delicious. Meals I still remember to this day. In the evening, check out the traditional Fado music of Lisbon. It is worthwhile to learn about this music type to get a better appreciation for the culture.
For modern and contemporary art, take the train (Linha de Cascais) toward the Belém district to visit the popular Berardo Collection. But that's just the start of the fun in Belem. Across from the Berardo is Discovery Monument, a large sculpted tower dedicated to the great Portuguese trade and exploration achievements of the 15th and 16th century. Nearby is the Jeronimos Monastery. This impressive UNESCO site from 1501 features ornate carvings and a temple-like church that houses the tomb of Vasco da Gama. Toward the water is one of the most notable sites in Portugal - the Tower of Belem. Constructed to overlook the Tagus River in the 1500s, it's a blend of architectural styles that I find beautifully quirky and fun. Before you leave Belem, you have to try the famously tasty custard tarts of Pasteis de Belem.
Continue your train ride to Cascais, about 45 minutes from Belém. This old fishing village is now packed with sun-seeking locals and tourists alike. And for good reason - not only is it pictueresque, but the seafood is top notch. My favorite place is O Pescador. If you want to be right on the beach, there are other options that tradeoff food quality for views. Be aware, you may see some nude bathers - not always a pretty sight!
Today, plan a day trip to Sintra. Because I love castles, I absolutely love Sintra. Take an hour train ride from Lisbon (Linha de Sintra) and then Bus 434 to avoid a 2-mile walk. The castles are clustered at the beginning of the Parque Natural de Sintra-Cascais. One of my all-time favorite sites is Pena Palace. You can't miss it becasue of its hilltop position and extreme coloring. It's a national monument, although it just from the 19th century. I won't explain too much more because there's real joy in exploring it yourself. Another castle that you must see is Castelo dos Mouros (Castle of the Moors). This castle is over 1,000 years old! Although it mostly ruins, walls, and an occasional tower, it is great to walk in something so old. The views are spectacular, making it worth the stairs. Last but not least is the National Palace of Sintra. It is amazing that this palace survived from the middle ages in such great shape. The interior definitely outshines the exterior. I was most impressed by the large kitchen and the state rooms.