Adventure Tactician

Three Days Larking in Lisbon

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Jeff Golenski

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In November of 2024, I was invited by the Jetpack Design team to their meetup in Lisbon, Portugal to collaborate on some feature improvement planning and integration to the Automattic for Agencies program that I had been working on. While we accomplished a lot, this post won’t be speaking anymore about work, but instead cover the amazing experience of Lisboa and the surrounding areas.

While enroute to Portugal, the plane flew right through a beautiful storm right before landing.

I had never been to Portugal before and was stoked to make the journey across the Atlantic to experience its rich history, culture, architecture, and of course, Ginjinha (a delightful sour cherry liqueur).

The only caveat being that due to some schedule conflicts, I only had 3 days to make this trip work, but I wasn’t going to let that stop me from hanging with some great colleagues and indulging in an excessive amount of Pastéis de Nata (delicious custard tarts).

View of Lisbon with colorful rooftops overlooking the Tagus River, featuring clouds and a distant bridge.
The view from our rental presented a breathtaking view of the rooftops throughout Lisbon

Lisbon boasts a wonderful cascade of architecture that overlooks the Tagus River, which is the longest river on the Iberian peninsula. Across the way from our rental, we could see the The 25 de Abril Bridge, which is a Golden Gate-style suspension bridge that connects Lisbon with Almada.

Beyond the bridge, the remarkable Santuário de Cristo Rei (Sanctuary of Christ the King) stands tall, keeping a watchful eye over mischievous designers sipping wine from their rooftop villas.

A sweeping panoramic view of the Lisbon skyline next to the Tagus River

Below the skyline, I was absolutely blown away at the vibrancy and color adorning the streets and alleys of Lisboa. Each building is a work of art, full of intricate geometric patterns, ornate railings, vining plants, and the occasional curious soul peeking out.

A view of colorful buildings in Lisbon, showcasing intricate tiles and balconies with wrought iron railings, bathed in warm sunlight.
Buildings throughout the city tightly lean up against each other in solidarity
A person looking out from a window of a traditional Portuguese building decorated with blue and white tiles, surrounded by a cobblestone sidewalk.
A curious fellow stuck his head out of the window to look at a nearby car accident

Architecture like this isn’t planned at once or built overnight, it’s the culmination of centuries of urban evolution, slowly built up by creativity over generations.

View of a building in Lisbon, Portugal, showcasing a balcony with plants and a blue sky above with scattered clouds and power lines.
Cables can often be seen connecting throughout the streets, almost like spiderwebs capturing tourists
A close-up view of a vibrant building facade in Lisbon, featuring ornate blue tiles, potted plants on balconies, and lush greenery climbing the walls.
Beautiful vining wysteria vertically connects many balconies throughout Lisbon
Narrow cobblestone street in Lisbon illuminated by street lamps at night, showcasing colorful buildings with balconies.
When night falls, the city lights expose a hint of mystery and drama in every alleyway.

The picturesque funicular system was one of my favorite stops in the city. Unlike normal trams running throughout the city, the small funicular cars are designed to climb up the steep hills throughout Lisbon.

Pictured below is the Ascensor da Bica, often regarded as Lisboa’s most idyllic funicular. You’ll notice the cable system above the car, which provides power, while the cables that move the cars are actually under the ground.

A picturesque funicular traveling down a steep street in Lisbon, surrounded by colorful buildings and cobblestone pathways.
Ascensor da Bica offers one of the most beautiful views of the city

As you peruse the city, you’ll notice one common denominator on almost every sidewalk. The imperfect, yet perfect, Portuguese Cobblestone. The meticulously placed white stone laid out in a mosaic-like pattern offers incredible contrast against of colors and patterns of the buildings above.

Close-up view of traditional Portuguese cobblestone pavement, featuring a mosaic pattern of white stones with some greenery in between.
Every centimeter of Intricately placed stone is unique.

Lisbon touts some serious visual history as well. Below, you’ll see a few exterior photos of Carmo Convent, which was built between 1389 and 1423. Tragically, an earthquake destroyed much of the church and its library in 1755. Why didn’t they rebuild, you ask? Check out the Wikipedia article for an interesting dive into its complex history following the quake.

A view of the ruins of a historic building against a blue sky with clouds, showcasing architectural details and textures of the stone structure.
The walls of Carmo Convent still stand tall, centuries after an earthquake destroyed most of the church
Low-angle view of a historic stone building against a blue sky with scattered clouds.

Of course, Lisbon isn’t all ancient stone and centuries-old charm. Outside the historic center, the estradas (roads) and autoestradas (highways) are impeccably maintained, curving around the city in a way that’s unexpectedly beautiful.

Gentle clouds sweep high above over the curving roadways

After the sun sets, warm mismatched glows illuminate the quaint streets of Lisboa, revealing even more European charm. Soft street lamps add drama to the old wooden doors and elevate the texture of ancient paint on every wall.

A night view of a bar named 'Salotito Divino' in Lisbon, showcasing its illuminated entrance and decorative tiled facade against the backdrop of a cobblestone street.
Modern bars and restaurants quietly hide behind beautiful cobblestone sidewalks
Night view of Lisbon with illuminated buildings, the Tagus River, and the 25 de Abril Bridge in the background.
At night Santuário de Cristo Rei (Sanctuary of Christ the King) glows above the skyline of Almada
A weathered black door with a number '10' above it, set against a pink wall with an ornate stone frame. Cobblestone path in front.
The well worn doors of private homes in every alley have so much charisma
A person stands casually next to a small, ornate door on a cobblestone street in Lisbon at night, surrounded by warm yellow walls and traditional architecture.
Filipe posed next to a particularly tiny door in one of the alleys.
An ornate wooden door with decorative glass panels, softly illuminated from behind, set against a dark background.

I’ll confess: the title of this post is a lie. My three-day sprint through Portugal didn’t involve only Lisbon. Filipe, Jetpack Design’s director and my good friend, happens to be a native of this remarkable country.

One day he treated us to a proper adventure: a mini road trip through the Portuguese coastline & countryside. We grabbed a van, piled in like a family driving to Wally World, and set off to discover whatever gems he had stashed up his sleeve.

Boca do Inferno in Cascais

Just West of Lisbon down estrada N6 (national road 6), we toured the coast for a while, where Filipe brought us to some extremely dramatic coastline known as Boca do Inferno in Cascais.

A panoramic view of a rocky coastline with the ocean in the background, featuring a distant ship sailing on the shimmering water under a clear sky.
Large tanker ships darted back and forth off the coast off Boca do Inferno

Boca do Inferno is quite a sight. Its sheer limestone cliffs take the full force of the crashing waves, while below, brilliant green water swirls with massive shoals of fish gliding just beneath the surface.

Shoals of fish can be seen darting around the deep green water near Boca do Inferno
View of the ocean through a metal fence, with soft reflections on the water's surface and a pinkish hue in the sky.
A picturesque view of the coastline in Cascais, Portugal, featuring cliffs and the Atlantic Ocean under a clear sky.
The cliffs at Boca do Inferno are layered like cake… make of stone

Sintra & Quinta da Regaleira

From Boca do Inferno, we followed the coastline west before turning north toward my favorite stop of the entire trip: Sintra.

Sintra is a sprawling town. Its nearly 320 sq. km (124 sq. miles) and packed with historical treasures like castles, palaces, gardens, and enough architectural splendor to keep you busy for days.

Our adventure had us meandering through the historic town center and into Quinta da Regaleira, an immaculate manor with a world-class garden and a deep, spiraling well that can make even seasoned adventurers feel a touch claustrophobic.

A scenic view of a historic castle in Sintra, perched on a rocky hilltop, with lush greenery and palm fronds framing the foreground under a soft, cloudy sky.
The Castle of the Moors, on the hilltops of Sintra as seen from the garden of Quinta da Regaleira
A historic and ornate castle-like structure against a bright blue sky, surrounded by lush greenery.
The ornate manor of Quinta da Regaleira was breathtaking
Sunlight streaming through the branches of a tree, creating a starburst effect in a forest setting.
Just before sunset, the light burst through the branches of the ancient trees within the garden
A Portuguese flag waving atop a historic building surrounded by trees and traditional architecture under a dark sky.
The flag of Portugal flies high above the historic downtown area of Sintra
A view of traditional Portuguese rooftops with red tiles and a satellite dish, featuring a vintage house facade with a balcony.
Layered rooftops added some splendid visual curiosity to the town surrounding Quinta da Regaleira
A scenic view of a hillside with a traditional house featuring a unique red-tiled roof, surrounded by lush greenery and trees, overlooking a distant landscape under a soft, warm sunset sky.
The manor at Quinta da Regaleira has a wonderful view of the rolling countryside
Close-up of Portuguese cobblestone pavement with dark stones and patches of green moss.
More ornate stone could be found everywhere in town
A scenic view of a lush garden pathway in Sintra, Portugal, showcasing tropical foliage and intricate stonework. People can be seen walking across a decorative bridge surrounded by greenery.
Gorgeous walking paths looped throughout Quinta da Regaleira under Castle of the Moors
A weathered blue door set against a yellow wall, adorned with ivy and small yellow flowers. A sign reading 'Quinta de S. Miguel' is visible above the door.
Ivy draped over the walls above doors throughout Sintra
Close-up of intricately carved stone railing featuring organic shapes and motifs, set against a backdrop of lush green foliage.
Intricate stonework adorned the walls of the manor at Quinta da Regaleira
A scenic tree-lined pathway in a lush green area, where several people walk leisurely along a cobblestone path bordered by plants and flowers.
A careful assortment of plants layered the paths throughout Quinta da Regaleira
A close view of ornate lion head door knockers on a wooden door, showcasing intricate details and craftsmanship.
Detailed sketch of a lion's head, featuring geometric patterns and architectural elements, set against a black background.

The Initiation Wells

Yep, you read that right. The Initiation Wells are two deep, walkable wells on the grounds of Quinta da Regaleira. Never meant for water, but allegedly for ceremonies and rituals.

Built between 1904 and 1910, the larger well is steeped in symbolism tied to death and rebirth, the Knights Templar, and other mystical traditions. It drops an impressive 27 meters (88 feet) and is fully accessible by a spiraling staircase.

A top-down view of a moss-covered stone well with several archways and a glimpse of light at the bottom.
The bottom of the deep Initiation Well felt miles away

Did we descend into the depths via that staircase? You bet we did. At the bottom, a stone compass marks the floor, adding to the whole mysterious, “secret-society initiation” vibe.

A view looking up inside a stone spiral tower, showcasing arched openings, columns, and natural light coming from above.
Once at the bottom, the claustrophobia really set in, but the view was sensational

The second well, often called the “unfinished well,” is smaller and not nearly as deep, but every bit as enchanting. I was especially captivated by the blanket of moss covering the slabs of stone within the unfinished well.

I’m fairly certain the designers of Elden Ring pulled some inspiration from this eerily beautiful place.

View looking up from the bottom of a moss-covered stone well, with tree branches and green leaves visible at the top.
The moss of the “unfinished well” was especially intriguing as the light created a beautiful green gradient

Praia do Guincho

After the sun began to set on Sintra, we departed and made way for the West coast of Portugal. After a short ride, we found a spot to capture the last glow of the sun at Praia do Guincho.

A silhouette of a person fishing on rocky shore during a colorful sunset, with vibrant orange and pink hues reflecting on the ocean surface.
A lone fisherman gazed out into the vast ocean, wondering where all fish went
Waves crash against Praia do Guincho
A serene coastal view at sunset, with gentle waves lapping against the shore, and a soft gradient of colors in the sky transitioning from orange to purple, capturing the tranquility of the ocean.
The moon added another layer of beauty above the orange gradient layered on the water
A twilight scene showcasing a dramatic sunset over the ocean, with silhouettes of buildings and people along the shoreline.
The moon glows bright above Hotel Fortaleza do Guincho
A silhouette of two people standing on a rocky coastline while watching a colorful sunset over the ocean.
This couple did not want to say goodbye to the sun

After a remarkable sunset, we piled back in the van and headed back to Lisboa. The next morning I was on a flight back stateside.

Muito obrigado por leres. Até à próxima viagem. 👋

This post was was made possible thanks to the impeccable guidance of Filipe.

Be sure to head to his site, MuteLife.com, to see similar visual journeys around the world. He’s much better at street and still life photography than I am, you’ll love it.

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