VERDICT: We gave 4 out of 5 tickets and here’s why!
👉 Lisbon Done Right: First-Time Experience + Smart Travel Strategy
We arrived in Chiado around noon, thinking it would be a relaxed afternoon in one of Lisbon’s most famous neighbourhoods. Instead, it turned into a full day of hills, hidden corners, historic sights, and one unforgettable cultural experience. From the world’s oldest bookstore to a roofless church in the heart of the city… Chiado kept giving us reasons to stay. And by 5:30, the perfect ending was still waiting.
From a 1732 bookstore to a church frozen in time, ending with one of Lisbon’s most powerful cultural experiences.
We took an Uber from our hotel and arrived in Chiado around noon, ready to spend the afternoon exploring one of Lisbon’s most well-known districts.
First things first, we stopped for lunch. We stopped at a temporary food and drink setup right at the top of the hill. It turned out to be one of the best little breaks of the day, snacks, drinks, and a wide-open view across Lisbon. The kind of spot you don’t plan for, but end up remembering.
It felt like the right way to begin here. Chiado has that easy mix of elegance and energy, with cafés, boutique shops, and streets that immediately make you want to slow down and just take it all in.
Of course, this is Lisbon… so slowing down doesn’t always mean flat ground. Even after spending four full days in the city, we still underestimated the hills. Chiado had us walking up, down, and back up again—but that’s part of what makes it memorable. Every corner feels different. One minute you’re on a quiet street, the next you’re in the middle of a lively square with street performers, cafés, and people just soaking it all in.
We visited Bertrand Bookstore, officially recognized as the oldest bookstore in the world, operating continuously for almost 300 years. Walking through it, you can feel the history, it’s the kind of place you don’t rush. Honestly, if we lived nearby, this would be a regular stop.
Founded in 1732 by French bookseller Pedro Faure, Livraria Bertrand is widely recognized by Guinness World Records as the oldest operating bookstore in the world. The original shop opened nearby on Rua Direita do Loreto, but after the devastating 1755 Lisbon earthquake destroyed much of the area, the bookstore was rebuilt and relocated to its current premises. Over the centuries, it became a cultural hub for Lisbon’s literary scene, frequented by prominent Portuguese writers and intellectuals. Walking through its interconnected rooms today, you’re not just browsing books, you’re stepping into nearly three centuries of continuous literary history.
Today, Livraria Bertrand is located at Rua Garrett 73–75, 1200-203 Lisbon, Portugal, right in the heart of Chiado. Despite its global recognition, it still feels grounded and authentic, less like a tourist attraction and more like a living bookstore. The classic wood interiors, vaulted ceilings, and quiet corners give it a timeless atmosphere, making it a place where visitors often linger longer than planned. It’s not just about buying a book, it’s about experiencing a piece of Lisbon’s cultural identity that has survived wars, earthquakes, and generations of change.
From there, we made our way toward the Carmo Convent.
Fado in Chiado, Lisbon: Hills, History & a 13th Century Roofless Church
Even from the outside, it stops you. This Gothic church dates back to the late 1300s but was severely damaged during the massive 1755 Lisbon earthquake. What remains today are the towering stone arches, completely open to the sky, left exactly as they were, as a reminder of that moment in history that reshaped the entire city.
- Built in 1389 as one of Lisbon’s most important Gothic religious buildings
- Severely damaged during the 1755 Lisbon earthquake, followed by fire
- The roof collapsed during mass, killing nearly all of the worshippers, one of the most tragic moments of the disaster
- Left intentionally roofless as a lasting memorial to the earthquake’s destruction
- Today operates partly as an archaeological museum, preserving artifacts beneath open skies
- 👉 Bottom line: It’s not just a ruin, it’s a preserved moment in Lisbon’s history.
Sadly we didn’t go inside, the lines were long, but even standing there, looking through the ruins, it’s one of those Lisbon moments that stays with you.
Not far from the famous bookstore we stumbled across an incredible church. It is called the Basilica dos Mártires.
This Basilica is one of Chiado’s most historically regarded churches, originally founded in the 12th century shortly after Lisbon was recaptured from Moorish rule. It was later destroyed in the 1755 earthquake and rebuilt in the late 18th century in a neoclassical style, giving it a refined yet understated presence compared to other Lisbon landmarks. Inside, you’ll find elegant altars, detailed artwork, and a calm, reflective atmosphere that contrasts sharply with the dramatic ruins of nearby Carmo Convent. Located at Rua Garrett 58, 1200-309 Lisbon, Portugal, it’s easy to walk past, but stepping inside offers a quieter, more intimate connection to Lisbon’s resilience and religious history.
From there, we continued exploring, taking in the cafés, the boutique shops, and the overall atmosphere. Chiado feels polished but still authentic, blending historic Lisbon with a slightly more modern, creative edge.
Then, at 5:30pm, the day shifted perfectly into evening.
We attended Fado in Chiado, a performance that’s been running for over 17 years. The setup is simple, two vocalists, an acoustic guitar, and the traditional Portuguese guitar, but the sound fills the room in a way that’s hard to describe. Fado is deeply emotional. It’s about longing, history, and everyday life and even if you don’t understand the words, you feel it.
The Fado in Chiado performance takes place at Rua da Misericórdia 14, 1200-273 Lisbon, Portugal, right in the heart of the Chiado district. The venue is a small, intimate theatre-style setting, just a short walk from Largo do Chiado and close to many of the area’s main cafés, shops, and landmarks.
After a full afternoon of walking, climbing, and exploring, sitting down for that performance just felt like the perfect way to end the day.
And after that, we made our way back to the hotel, a little tired, slightly hill-tested, but very glad we came.
Chiado gave us history, atmosphere, culture… and a proper Lisbon workout all in one afternoon.
⭐ Key Standout Reasons for a Return Ticket to Chiado
- Layered history in a compact area; from medieval ruins to diverse culture
- Bertrand Bookstore; the oldest operating bookstore in the world, and still thriving. Confirmed by the Guinness Book of Records.
- Carmo Convent; one of Lisbon’s most visually striking and historically powerful landmarks
- Authentic Lisbon atmosphere; cafés, boutiques, and walkable streets (& hills) with character
- Elevated viewpoints throughout Chiado: views appear when you least expect them
- Fado in Chiado: an intimate, emotional cultural experience that completes the day
- Perfect afternoon-to-evening transition: one of the best districts to experience Lisbon’s rhythm
- 🎟️ Return Ticket Rating: 4.0 / 5
With every trip, we offer feedback to travel companies along with honest views for you, the reader. We rate adventures on a scale of one to five tickets, judged on quality, service, memorability, and price. A perfect ‘Ticket Rating’ of a five-ticket score means the experience was flawless and we’d eagerly return. Your desire to go back is the ultimate measure of a trip’s worth. Exclusive to My Return Ticket.
