Lisbon holds a lull, yet intimate effervesce within its narrow environs and bustling centers. Its gothic grit and white-domed cathedrals genuinely feel like you’ve taken a step back in time. Portugal’s most populous municipality has a rich history, with influences from the Phoenicians, the Romans, the Visigoths, and the Moors. With its perfect blend of old and new, coastlines and cityscapes, cheap booze and free expression, it is a truly authentic and beloved destination. For those interested in delectable local cuisine, mild weather year-round and friendly locals, Lisbon will not disappoint. Below you will find an itinerary for an actioned packed two days in this delightful city, and some must-see surrounds.
Day 1- Discover the heart of Lisbon
Lisbon is a city with so much culture and history to uncover. The city experienced a devastating earthquake back in 1755, followed by an equally destructive tsunami, leaving the city decimated. As Lisbon was rebuilt over time, an emphasis on maintaining what was before the disasters hit was at the forefront of mind. Many of what you see today is a rebuild, with tidbits of pre-earthquake Lisbon scattered throughout the city. Many buildings following the devastation were built strategically to withstand seismic activity.
Consider starting your day in the heart of the city at Rossio Square. This lively square is characterized by its baroque fountains and a towering statue of Dom Pedro IV. The square represents wisdom, strength, and moderation to the Portuguese people. Consider grabbing a coffee and pastry at one of the atmospheric cafes that surround its perimeter, before heading over to the Alfama district, also known as the Old Quarter. Stroll its labyrinth, cobblestone alleys taking in many iconic and significant sights of the city, such as the Lisbon Cathedral, and the Moorish St. George’s Castle. For the best panoramic view of the city, head to the Miradouro da Senhora do Monte lookout.
From Alfama you can jump on the 15E tram along the Tagus River and head to Belem, the city's most monumental district. Originally the departure point for voyages out to India, East Africa and Brazil, this laidback area is home to several World Heritage Sites, such as the Torre de Belem and Mosteirio dos Jeronimos, both examples of outstanding Portuguese architecture. While here, get a taste of the best custard tarts in the world fresh out the oven at Fabrica Pasteis de Belem, the first bakery to produce this now internationally prized treat. It’s worth the wait!
Like most European cities, dinner is served later in Lisbon than in the Western world. With an 8 pm dinner call, I recommend stopping in at PARK for a sunset cocktail with a view before heading to dinner at Mini-Bar (reservation strongly recommended). PARK is a tricky place to find, mostly because it is literally a rooftop bar on top of an unassuming, multi-leveled parking lot. Cocktails are a bit more expensive here than you’ll find in the majority of Lisbon, but it's worth it for the view. Mini-Bar is a fabulous restaurant from Jose Avillez that is a gastronomic experience for the senses. Get the feel of an intimate, Michelin level restaurant and service, without the major price tag. Each course is set as playful theatrical acts, giving a fresh and innovative meaning to “dinner and a show”. I highly recommend the Tuna tartar temaki cones and the mini “bite-able” cocktails – yes you read that right. For a more relaxed environment, I recommend Duque.
If you still have some kick left in you after your long day of touring the city, head to Pink Street. Not only is this area eye-catchingly adorable due to its literal bright pink painted street, but it is also home to the best bars in the whole city. Officially called Rua Nova do Carvalho in the Cais do Sodre neighborhood, this use to be Lisbon’s red-light district. Bars in this area stay open later than in sister “party district” Barrio Alto. Some fun suggestions to check out: Pensão Amor, The Music Box, and Europa.
Day 2- Sintra and the coast
Hopefully, you didn’t stay up too late last night, because to hit everything on Day 2’s list, you’re going to want to be up early! For the sites seen on today’s excursion, you’re going to need a car. Driving in Lisbon is quite simple once you’re out of the narrow roads downtown. If you’re not up for renting a vehicle, consider booking a small-group or private tour. Either way, prepare to see some of central Portugal’s best.
Today you’ll begin the journey west towards the magical town of Sintra and the iconic Pena Palace. En route, consider stopping at any of these towns for some locally immersive experiences:
Estoril is a resort town, famous as the home of the Casino Estoril and the emblematic Hotel Palácio. The hotel was a known rendezvous point for British and German WWII spies and is featured in James Bond’s “On Her Majesty’s Secret Service”. Stroll along the Tamariz Beach promenade, window shopping or grabbing breakfast at a waterfront eatery, and marvel upon the 17th century Forte da Cruz castle.
Cascais is a quaint and charming fishing village turned plush resort town on the Portugal Riviera. Discover stunning beaches, opulent mansions, and noteworthy museums in this tiny yet lavish coastal settlement.
The westernmost point of continental Europe is Cabo de Roca where you can gaze out over the endless Atlantic Ocean, undoubtedly a very important site for sailors and explorers alike. Depending on what time of day you’re out, this could be your final stop en route home, as the sunsets here are spectacular as the sun melts into the sea.
Quinta de la Regaleira was probably my favorite stop on the way to Pena Palace. Located right next to Sintra, this UNESCO site is the old residence of a rich Brazilian mine owner, and the secrets of these sprawling, neo-gothic grounds are just as alluring as the architecture itself. The owner was fascinated by the secret cultish rulings of the stonemasons and the Knights of Templar, and this is evident in the many hidden grottos, secret passageways, and underground stairwells and jail cells, all of which you can access (be careful on the winding staircase – it gets very dark, so I suggest bringing your phone or a flashlight for light).
There are endless photo opportunities, and the history of the place is overall fascinating. In my opinion, it is as much of a must-see as Pena Palace. Plus, just a short distance away is the storybook town of Sintra. Quaint and whimsical handicraft shops and traditional pastry cafes line the winding streets, making for an ideal stop before hiking to the top of the mountain to Pena Palace (it is not a “hike” per se, more so a long, inclined driveway – if you have any mobility issues, I’d recommend booking a bus ride to the top. If not, it is not that difficult to scale).
This 19th-century incredible Pena Palace is a combination of architectural styles, colors, and shapes with breathtaking views of the valleys that surround. Just one step onto its affluent and regal grounds and you feel like you are stepping into a fairy-tale. It’s best to go as early as you can to avoid crowds, or during the week. You can book a tour to walk the inside where much of the original furniture remains today. There is also a gift shop inside that sells bottles of wine, as well as a spacious rooftop patio which was the perfect way to end our busy day trip out of Lisbon.
The name of the game in this stunning city is to eat, drink and be merry, all while seeing some of Europe's most stunning and protected sites. Portugal should be on every explorers bucket list, and there's no better place to start than Lisbon.
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