Lisbon has a quintessential old European city charm to it. Compared to Madrid , it is more rundown though.

Day 1 - Baixa-Chiado area

Check out the main square (Baixa-Chiado), see the oldest running bookstore , and learn the history of the various parts by doing a walking tour .

A tall downtown building with a modern glass facade stands prominently in the cityscape, reflecting adjacent structures and a clear blue sky, indicating a busy urban environment.
A cityscape with high-rise buildings reflecting adjacent structures, under a clear blue sky, indicating a busy urban environment.
View of a downtown area with tall buildings, a busy urban landscape, and clear blue skies
A large urban area with several buildings
An old illustration depicts Lisbon in ruins after the 1755 earthquake, with damaged buildings and debris scattered across the cityscape.

A big earthquake came in 1755 in Lisbon. Apart from the red-light district, most of the city was destroyed and that made people start questioning God. One Church, Convento De Carmo, has some last ruins to indicate the impact of the earthquake.

The ruins of Convento De Carmo, highlighting the impact of an earthquake, situated in a historical area with remnants of architectural structures.

Day 2 - Alfama district

Alfama district consists of narrow streets and small houses. It was built during the Muslim Moor rule in the 7th century and the overall architecture hasn’t changed much since then. Without a walking tour, it is easy to miss subtle gems here.

A vintage tram navigates a narrow street, evoking historical charm in a quaint old town setting
A tram in a city setting with surrounding urban landscape in Bélem
A scenic view of the Bélem district in Lisbon, capturing architectural landmarks surrounded by a picturesque urban landscape.

Day 3 - Bélem district

The most majestic and picturesque district of Lisbon. Its name derives from Bethlehem. At one time, when Pope use to grant recognition to countries, Portugal’s king built a lot of churches, in the hope of getting recognition from the Pope.

A Gothic-style church with intricate detailing stands prominently, showcasing architectural grandeur
A scenic train journey to Sintra is highlighted, with a picturesque view of trains that operate nearly 24 hours, providing transportation for travelers.

Day 4 - Sintra

Take a train journey to Sintra. The trains run for almost 24 hours from the Rossio station . The round trip ticket costs ~4.5 Euro. Sintra, higher up in the mountains, is both majestic and classy. The castles are worth checking out there. I would highly recommend checking out Quinta Da Regalerira castle first, then the colorful Pena castle. And if you still have time and interest left, go to Montserrat castle.

Quinta Da Regalerira is accessible by walking from the main town. The entrance ticket cost 10 Euro.

Quinta Da Regalerira

Quinta Da Regalerira

Quinta Da Regaleira landscape with lush greenery and intricate architecture. There is a mention of transportation costs: Tuktuk for 5 Euro, another option is a bus.

For Pena castle, which is high up in the mountain, I took a 5 Euro Tuktuk. You can take a bus for ~3 Euro as well. The entrance ticket costs 14 euros. If you are budget-constrained then buy a 7.5 Euro external ticket. There isn’t a lot to see inside anyway. Once you come out, do a walk around in the park, it is a nice hike worthy in itself.

View of Pena Palace, a vibrant multicolored castle with ornate architecture situated on a hilltop surrounded by lush greenery, under a clear blue sky.
Pena Palace in Sintra, Portugal, is a colorful, historic castle on a hilltop surrounded by lush greenery, showcasing 19th-century Romantic architecture and intricate details
A colorful, historic castle stands majestically on a hill surrounded by lush greenery, showcasing vibrant architectural styles and attracting tourists.
Pena Palace in Sintra stands majestically on a hilltop, showcasing vibrant colors and Romantic architectural style amidst lush green surroundings.
Pena Palace, a colorful and ornate architectural structure, sits atop a lush, forested hill, showcasing a blend of Romanticist style with sweeping views of surrounding landscapes.

Note:

  1. The public transport is great and cheap (6€/24-hours for unlimited trips).
  2. Food choices are ample, especially, for vegetarians.
  3. There are rundown buildings and urban blight even in the touristy parts of the city. The only city, that I have seen with more blight in Detroit .