36 Hour Travel Guide: Lisbon, Portugal

Rob Monaco, Contributor

A new section in The Harbus profiling the exotic places HBS students visit on long weekends, and the interesting things to do, see, and eat while you’re there.

With an air of majestic elegance, historic beauty and envious affordability, Lisbon, the capital city of Portugal, offers visitors a rich blend of Western European heritage, several extravagant monuments, vibrant nightlife and the charm of authentic Portuguese culture. With a seven-hour direct flight from Boston (TAP Airlines) and a beautiful year-round climate, Lisbon is a stunning destination for anyone looking for an unforgettable weekend getaway.

This fall, a group of RCs made it over to Lisbon for three days over Veterans Day Weekend, and we were hoping to pass along helpful hints for any prospective visitors. Three full days is ideal for visiting, which allows visitors to spend a day in Baixa and Alfama (both within Lisbon), take a day trip to Sintra or Cascais (both outside Lisbon) and explore Belem and Parque das Nações on the final day.

Pro-tip: make sure you bring comfortable sneakers. Lisbon is spread across seven hills, so expect to do a lot of walking, particularly on some very steep side streets. Also, have your student ID handy. All the tourist venues offer discounted student tickets for visiting the sites and exhibits.

Where to Stay

It is generally recommended that tourists stay close to the historic centre of Baixa, Chiado or Bairro Alto. These areas are right at the center of all the main attractions, within walking distance of many bars and restaurants, and close to the train station should you decide to take a day trip outside Lisbon. Relative to other European cities, Lisbon offers exceptional value for your money in terms of food, drink and lodging. Lisbon is Airbnb and Uber friendly, making it easy to navigate the narrow and winding cobblestone streets.

Tourist Attractions: Travel Itinerary

Upon arriving, visitors can gain a true appreciation of Lisbon by sightseeing the districts of Baixa and Alfama by foot. Both have much to offer visitors in terms of unique monuments and attractions, but reflect two very different sides of country’s storied history. Baixa, the heart of Lisbon, was once destroyed by earthquake and reconstructed as one of the first examples of the grid and block layout that is now fairly common throughout the western world.

Full of magnificent plazas and cafes, Baixa is a great place to try some Portuguese delicacies. Make sure you try a small glass of Ginja, a famous cherry liquor and Pasteis de nata, a delicious kind of custard tart (though the original recipe can be found in Belem at Antiga Confeitaria).

Over in Alfama, the oldest district of Lisbon, be sure to visit the Lisbon Castle (Castelo Sao Jorge), the site of absolutely stunning views and where the Christian Crusaders defeated the North African Moors in 1147. Other historic spots: Se Cathedral (12th century site of an important Moorish mosque), National Pantheon (burial place of explorers Vasco de Gama and Henry the Navigator) and the Church of Saint Anthony, the Patron Saint of lovers. Tradition has it, if you can land a coin in the book of the statue of Saint Anthony, you will find a new or better partner!

The next day, it may be worth taking an inexpensive 40-minute train ride (the 434 route) over to Sintra. Sintra is the most popular day trip from Lisbon, a small town with more than 10 national monuments, including palaces, ancient ruins and decorative houses. The three main tourist attractions in Sintra are the National Palace, the Moors Castle and the Pena Palace. In the center of town, you’ll find pretty cobbled streets lined with traditional shops and cafes, all centered around the Gothic-styled National Palace (Palacio Nacional), the lavish home of Portuguese nobility between the 15th and 19th centuries. The Moors Castle (Castelo dos Mouros) is an ancient ruined castle that dates back to the 8th century that sits higher than the National Palace and offers panoramic views of the entire surrounding region of Portugal. Lastly, the vividly colorful Pena Palace, surrounded by pine forests, is considered one of the Seven Wonders of Portugal, one of the major expressions of 19th-century Romanticism in the world.

If you’d rather stick to the wild surfing beaches (and possibly run into Christiano Ronaldo), Cascais may be a better day-trip option for Day 2. Cascais is a charming and prosperous fishing town that sits on the western coastline of Lisbon. In this lively resort town, you could check out the Guincho surf beach, one of the many parks, or a few of the smaller free museums. Castro Guimaraes Museum is the most famous monument here, boasting impressive 19th century architecture and exhibits. If you enjoy hiking, Serra de Sintra National Park is a scenic site to visit in Cascais.

On the last day, Belem and Parque das Nações are solid options for taking in more Portuguese culture. Belem is roughly 5km west of downtown Lisbon (15 minutes by train). The best activity in Belem is a half hour walk from Pastéis de Belem to the Belem Tower. This route passes the Mosteiro dos Jeronimos, the Discoveries Monument and goes through the Jardim da Praça do Império and the Jardim da Torre de Belem (two carefully maintained parks in the area). The Mosteiro dos Jeronimos is a stone-carved monastery that was closely associated with the early Portuguese explorers. For the history buffs, the Belem Tower is a North African inspired fort that was built to protect the country from sea-bound attack. Lastly, Parque das Nações is a great spot for children, home of the Lisbon aquarium that is set up into four huge tanks representing the world’s four oceans. Also in this park, you can enjoy a cable car ride and visit Torre Vasco de Gamma, Lisbon’s tallest building that offers views over the Tejo River and Europe’s longest bridge over water.


I’ll leave the best restaurant recommendations to TripAdvisor and the Internet based on your preferences, but I highly recommend visiting The Rubieria, better known as the Time Out Market at least once. Opened in 2014 and attracting two million visitors a year, this 75,000 square-foot marketplace offers virtually every type of cuisine in one large, boisterous open space. With over thirty stalls (each chosen as being one of the best foods prepared by the best local chefs), packed side by side, visitors are able to sample the very best food and drink combinations that Portugal has to offer. Each entree is priced between $10 – $20, offering exceptional value for the quality and portion-size of the food.

You will often hear tourists making claim that no trip to Lisbon is complete without experiencing a Fado dinner. Fado is a type of live folk music, often sung by a lone female singer accompanied by a classical guitar. The music tends to be haunting and mournful, with lyrics related to the darker elements of love, death and sadness. Amalia Rodrigues and Cristina Branco are the more famous artists of the genre who typically perform at Fado clubs. Fair warning: our Airbnb host laughed at us when we inquired about the Fado dinner. Most Fado restaurants happen to be tourist traps, offering very high priced tickets for little value, so make sure you do additional diligence before signing up for one!

Nightlife & Shopping

For the party people, the Bairro Alto district (or Rua Nova do Carvalho, better known as The Pink Street) are where you can find the more populated bars in Lisbon where socialites tend to start their nights. Later on, you will want to make your way nearby to Lisbon’s premier nightclub called Lux, a three story discotheque that offers a variety of music options until sunrise. Other popular clubs worth checking out include: Urban Beach, Incognito and Main.

For any shoppers out there, Avenida da Liberdade is Lisbon’s most stylish shopping center that runs across a long tree-lined street. At the bottom of the avenue sits the Praca Restauradores, a plaza with a large obelisk and an art deco theatre. Nearby this avenue is the Parque Eduardo VII, a park that stretches all the way back to Baixa, providing for a pleasant walk back in the late afternoon.

With lots of beautiful sights and a little bit of everything – Lisbon has so much to offer anyone looking to visit. It may be time to go back, and this time to check out Porto.


Rob Monaco (HBS 2018) enjoys a wide variety of professional interests including investing, entrepreneurship and behavioral economics.  Prior to HBS, Rob worked in investment banking and private equity, and now hopes to apply his finance experience to a more global context, particularly to small business building and promoting education in the developing economies of Latin America where he enjoys spending time with his family.  An avid sports fan and follower of the New York franchises, Rob enjoys playing basketball and flag football in his free time, and is now really focused on improving his golf and tennis game.