The absolute best Lisbon getaway: a 5 day Itinerary with Must See Stops

Posted by Live The World on August 26th, 2022

Charismatic and charming Lisbon is a city that catches the attention of travelers in an understated way.

The region and surroundings of Lisbon are usually not the first places in Europe that one thinks of, but when you’re here, like a spell, people often find themselves enchanted by the plethora of things to do and see.

From the average 300 days of sunshine that Lisbon gets per year, to the rambunctious markets, historic architecture, emerging culinary scene, and notorious nightlife - the capital city of Portugal is one not to miss out on, and to find yourself coming back to over and over again. 

What’s even more under the radar to a lot of travelers are the adventures you can have surrounding Lisbon. This region - from Sintra, Berlenga Island to Arrabida Natural Park makes tantalizing day trips for anyone looking to get out in nature, mix things up from the city breaks, and soak up why this corner of Portugal is truly like a daydream.

Know Before You Go


A long favorite city getaway for Europeans during the winter and summer - Lisbon and the surrounding area seem to be perfect for a holiday any time of the year. 

  • No wonder why! During the winter months from November to February, Lisbon has the mildest winter out of any major European city, ranging between 8 and 10 °C - and that’s the lowest at night. For those sun-seekers during the usual grey European winters, Lisbon is the perfect place to be - with an average of 9 hours of sunlight in the winter. 
  • During the summer months from June to August, the temperature rises up to an average of 28 until it cools down in late September. This makes the beaches in Lisbon and the surroundings perfect for swimming for many months through to autumn. 
  • The shoulder season in Lisbon and the surrounding areas ranges from a balmy 18 °C to 22 °C. These months from March-May and from September to early November make a great time to explore the capital of Portugal without a large number of crowds during the summer.

    Day 1 - Lisbon: exploring Baixa, Chiado, and Alfama neighborhoods

    Built on 7 hills by the Tagus River, wherever you are in Lisbon, it’ll always feel like there’s a view. That’s because your eyes will marvel at sights like the city’s matching orange tile rooftops, sweeping grand cathedrals, or the colorful tiled art buildings - a true visual feast of a city. 

    Start your Lisbon trip off at Parque Eduardo VII, where if you stand at the very top of the well-manicured lawn, you’ll have a pretty good first impression of what the city is. The view looks over the Tagus River, and the many buildings perched on the hills of Lisbon. While you’re at the park, be sure to explore the Estufa Fria, an immaculate greenhouse that has an array of ponds,  and various gardens that are filled with diverse flora and fauna.

    From here you can either continue walking or biking down to Rossio Square, which is the heart of the capital city. Lisbon is known for its safe and well-connected cycling lanes that make biking an easy way to get around and see the city. If you decide to book a bike tour around Lisbon, you will see the city in a fun way at a comfortable pace. Once you’re at Rossio Square, you can have a drink at one of many old-world European cafes or just take in the architecture. The wavy pattern of the square’s cobblestones is dazzlingly hypnotic, just like the beauty of the two baroque fountains here. You’ll also spot the neoclassical Dona Maria II National Theater, which has watched over this atmospheric center since the 1840s. 

    Make your way down Rua Augusta, a street made for leisure strolls since it’s completely pedestrian-friendly. This street is smack middle of the Baixa district, which is Lisbon’s downtown with grand classical buildings all around you to remind you of the deep heritage this city has. None truer of this is Commerce Square, or Praça do Comércio, which is a representation of the Portuguese empire’s reach and wealth at the height of the late 18th century. The iconic Arco da Rua Augusta guards the square but also has an observation platform at the top that gives you a great sight of Rue Augusta. Architecture lovers shouldn’t miss the Elevador de Santa Justa, a Gothic-sampled wrought-iron lift that still functions today and that you can take up to the viewing platform and walkway.

    In the later part of your day, from the Baixa district, we’ll explore the Chiado and Alfama neighborhoods. You can do a walking tour of Lisbon through these neighborhoods with a local guide that goes in-depth with each highlight stop of the city. 

    Chiado is Lisbon’s most glamorous neighbourhood, with well-preserved pristine buildings harking back to the late 1700s. This glitziness shimmers in the architecture in the neighborhood too - with Basílica dos Mártires being one of the more gorgeous basilicas in the city. I don’t want to spoil too much, but if you step inside the baroque and neoclassical architecture, have a lookup! The ceiling paints the story and glories of Afonso Henriques, Portugal’s first king. 

    Amongst the many art galleries in this neighborhood, the National Museum of Contemporary Art of Chiado stands out. The museum celebrates Portuguese artists, highlighting the country’s cultural and creative scene. If you have time and are an art enthusiast, don’t miss out on the wide range of collection that is on display from paintings to installations, photography and sculptures. 

    The 14th-century Convento do Carmo is a gothic ruin with arches underneath a clear sky due to the roof never being repaired. It’s a sight to behold, leaving you with a chillingly haunting feeling amongst the leftover disintegrated convent.

    If you’re a book lover and have a love for old-world bookstores, definitely check out Bertrand Bookstore while you’re in Chiado. When I mean old - I mean, they’re literally the oldest bookstore in the world with a Guinness World Record hanging in the door to prove it! 

    If you choose to do a walking tour of Lisbon, it’ll wrap up in Alfama, which coincides with this itinerary for the day. Alfama is Lisbon’s most historical neighbourhood - with civilisations stacked on top of each from the Romans, Visigoths, Moors and Germanic tribes. Lisbon is one Instaworthy city, but most feel the neighbourhood of Alfama is the most picturesque of all. 

    Get lost in the labyrinthine cobblestone alleys, looking up at the numerous pastel-coloured and tile-covered homes of Alfama. You can take tram 28 - yes, the iconic yellow trams that have become one of the symbols of Lisbon, into Alfama. Explore St. George's Castle, which can be seen from almost anywhere around Lisbon since it’s on such a high hill. Since we’re already so high up, a nearby walk away is the Portas do Sol Viewpoint. This is your classic terrace panorama of Lisbon - where you can see out to see the city’s most emblematic sights. From this viewpoint, with the cathedrals and water in the distance, you get the best of what makes Lisbon so beloved by locals and travelers alike! 

    The Lisbon Cathedral and the National Pantheon are other highlights of Alfama, two glorious architectural beauty contrasting yet complimenting the Capital city. The cathedral is gothic and almost 9 centuries old! While the all-white pantheon has a striking dome, that has a grand terrace crowning over the city. 

    Now for the romantics and sunset lovers (who doesn’t love a good sunset spot?) end your day at Santa Luzia Viewpoint. Consider this spot the city’s own public balcony, where you can stroll underneath classical columns that are wrapped in fully blossomed bougainvillea flowers. If you’re here at sundown, the view of the Tagus River and Lisbon will look like it's set in a blaze of soft orange hues. I know, cue the awws!

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Joined: June 21st, 2022
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