For our third day in Portugal, we left the hustle and bustle of Lisbon behind to embark on one of the most famous day-trip loops in Europe: winding up into the misty, castle-topped hills of Sintra, tracing the wild Atlantic coast out to Cabo da Roca, and catching our breath in the sun-drenched seaside town of Cascais.
It was a day packed with fairytale architecture, local traditions, dramatic ocean cliffs, and royal history—and we returned to Lisbon that night completely exhausted, but with hearts full of happy memories.
Exploring Sintra & A Sweet Local Tradition
Our morning began in Vila de Sintra, the historic town center tucked at the foot of the Sintra Mountains. Sintra feels like it was ripped straight from the pages of a storybook—cobblestone alleys, pastel-painted buildings, and lush pine forests blanketing the peaks above.
A Quick Sip of Ginjinha 🍒
While wandering through the town’s narrow streets, we made a essential stop at a local tavern to try a quintessential Portuguese tradition: Ginjinha (or simply Ginja). Ginjinha is a sweet, ruby-red liqueur made by infusing sour cherries (ginjas) in alcohol (often aguardente brandy) alongside sugar and cinnamon.
- The Monastic Recipe: The drink was originally created by a Portuguese friar who infused the fruit to create a digestive elixir.
- The Chocolate Twist: While traditionally served in a glass with a infused cherry at the bottom, local vendors in Sintra and Óbidos serve it in edible dark chocolate shot cups! You drink the tart cherry liqueur first, and then eat the chocolate cup—a delicious combination of sweet, tart, and rich chocolate.
Deep Historical Context: The Royal Summer Sanctuary
Sintra isn’t just picturesque; it holds a unique microclimate. Because the mountain ridge catches moisture from the Atlantic, Sintra is cooler, greener, and mistier than Lisbon.
- For over a thousand years, it served as a retreat from the summer heat—first for Moorish rulers who built the hilltop Moorish Castle in the 8th century, and later for Portuguese kings who built the Palácio Nacional de Sintra and the fantastical, colorful Pena Palace (Palácio da Pena).
- In the 19th century, Sintra became the global capital of Romantic Architecture, blending Gothic, Egyptian, Moorish, and Renaissance revival styles into eccentric estates like Quinta da Regaleira.
🇺🇸 USA Connection: When British poet Lord Byron visited Sintra in 1809, he called it a “Glorious Eden” in Childe Harold’s Pilgrimage. His writings triggered a wave of 19th-century American travelers and diplomats—including American author Washington Irving (author of The Legend of Sleepy Hollow)—to travel to Sintra.
Later, during World War II, neutral Portugal became Europe’s espionage capital. Wealthy American diplomats, OSS officers, and European royal refugees used Sintra’s secluded palaces as hidden safehouses away from wartime surveillance in Lisbon.
Cabo da Roca: Standing at the Edge of Continental Europe
From Sintra, our route wound down through the coastal mountains toward the roaring Atlantic until we reached Cabo da Roca.
Standing 460 feet (140 meters) above the crashing ocean, Cabo da Roca is officially the westernmost point of continental Europe (38∘47′N,9∘30′W).
At the edge of the cliffs stands a stone monument inscribed with a famous line by 16th-century Portuguese epic poet Luís de Camões:
“Onde a terra acaba e o mar começa”
(“Where the land ends and the sea begins”)
Historical Significance
To ancient Romans, this headland was known as Promontorium Magnum. During the Age of Discovery, sailors watched this exact lighthouse—built in 1772, making it one of the oldest in Portugal—fade into the horizon as they set sail into uncharted ocean waters.
🇺🇸 USA Connection: If you stand at the monument and look directly west across the open Atlantic ocean, you are facing North America on almost the exact same latitude line as Washington D.C., Maryland, and Northern Virginia!
In the 19th and early 20th centuries, Cabo da Roca served as a crucial geographical landmark for transatlantic steamships and early naval navigation connecting New York Harbor with the Mediterranean.
Coastal Elegance in Cascais
Cascais (pronounced kush-KAISH) is a chic resort town with paved black-and-white wave-patterned pedestrian streets, historic fortresses, and calm sandy coves.
From Fishing Village to Royal Riviera
For centuries, Cascais was simply a quiet fishing village supplying seafood to Lisbon. Everything changed in 1870, when King Luís I transformed the 15th-century Citadel of Cascais into his official summer residence. Royal court society quickly followed, turning Cascais into a glamorous resort filled with grand villas, manicured gardens, and seaside promenades.
🇺🇸 USA Connection: During WWII, because Portugal remained strictly neutral, Cascais and neighboring Estoril became known as the “Coast of Kings.” Deposed monarchs from Spain, Italy, and Romania lived here in exile alongside international spies.
British naval intelligence officer Ian Fleming was stationed nearby alongside American OSS agents. It was during his time monitoring German double agents at the Casino Estoril in Cascais that Fleming was inspired to create the character of James Bond and write his very first 007 novel, Casino Royale!
Returning to Lisbon: Happy & Exhausted
By the time we headed back along the coastal road toward Lisbon, our legs were tired from climbing hills, our jackets smelled like ocean salt, and we had a sweet lingering taste of chocolate and sour cherry.
Combining the fairytale magic of Sintra, the raw nature of Cabo da Roca, and the seaside elegance of Cascais into a single day trip was an absolute whirlwind, but easily one of the highlights of our entire time in Portugal!