The Magic of Sintra: The Ultimate Three-Day Itinerary

With its fairy-tale castles and an alluring blend of Gothic, Egyptian, Moorish and Renaissance history, Sintra should be more than just a day trip from Lisbon. Indagare's Abby Sandman crafts the ultimate itinerary. Plus, experience a taste of of Sintra on our upcoming Insider Journey to Portugal, alongside expert art historian and horticulturist (and Indagare-favorite host) Amy Kupec Larue.

The limestone grows slick beneath my fingers as we wind down, down, down… and the moss that clings to the cascading neo-Gothic archways glows in an emerald haze as the air chills and thickens deep inside the well of Quinta da Regaleira, an eccentric 16th-century estate just outside Lisbon. While descending into the inverted tower of this UNESCO World Heritage site (meant to symbolize the nine circles of Dante’s Inferno), it becomes perfectly plain that it was not designed to be a well at all. A ceremonial gateway to a labyrinth of tunnels beneath, this is a hidden passageway to a spiritual place, rumored to be used for initiations to the Knights Templar. The myth of this site weighs heavy as we reach the distinctive Templar Cross intertwined with tiles at the base of the well, a symbol of the Freemasons’ doctrine—although no one can say for sure whether the property’s owner was himself a Freemason or simply fascinated by the occult.

Sintra is full of stories like this one—secret histories and myths and castles and palaces, all enveloped in a verdant wonderland of feathery ferns, desert flowers and forests. Snapshots of Portugal’s history emerge amid the mountaintops: ruins of eighth-century battlements from the Umayyad Caliphate-era, scarlet turrets of a 19th-century Romantic palace and the dramatic spires of a neo-Gothic manor house—all paired with Michelin-starred restaurants, luxurious hotel accommodations and mild weather year-round— make it an essential addition to any Lisbon trip.

Sintra in Three Days

Arrive early to avoid the crowds at Pena Palace and its spectacular gardens. A blend of Moorish, Gothic and Manueline architecture, the red and yellow crenellated towers of this eclectic palace are visible for miles and magnificent to behold up close, surrounded by flowers and plants from every continent as well as winding pathways, especially in warmer months. After lunch, head back to your hotel for some relaxation and to take in the views. Try Basque cuisine at Penha Longa Resort’s new Eneko Lisboa, a Michelin-starred restaurant headed by chef Eneko Axta, whose restaurants have earned six Michelin stars.

Head to Quinta da Regaleira, the neo-Gothic masterpiece tucked into the side of a mountain overlooking Sintra’s historic downtown. This sprawling early-20th-century property is rich with secrets and stories, with symbols of heaven and hell, birth and death hidden throughout. Tunnels and mystical pools lurk underground while spiraling towers and an intricate manor house dominate above. Head deeper into the mountains to the secluded Park and Palace of Monserrate, with its intoxicating mix of Romantic, neo-Gothic and Islamic architecture and mesmerizing carvings depicting exotic flora and fauna. The serpentine paths of the park are equally magical, especially in the spring when flowers are in full bloom. From there, head to a late seaside lunch of fresh seafood at Restaurant o Croa. Whether you are guests or not, take part of the afternoon to wander the grounds of Tivoli Palácio Seteais, an 18th-century palace turned hotel, before enjoying dinner at the Seteais restaurant on the grounds.

Hike the trails through Sintra National Park to the mountaintop ruins of the Moorish castle above Sintra, where you can explore winding stone walls, eighth-century battlements and towers—as well as sweeping views of Sintra and the Pena Palace. On the way down, follow the path toward Pena Palace and visit the beautiful Mediterranean Villa Sassetti. After the hike, have lunch at Restaurant Piscina Azenhas do Mar before heading into Sintra’s historic downtown to wander around (or tour) the National Palace of Sintra. Grab a tasty snack at Casa Piriquito, best known for their queijadas (sweet cheese biscuits) and travesseiros en quijidas (puff pastries with eggs and almond cream). For a farewell meal, enjoy dinner at LAB, which received its first Michelin star this year.

Experience a taste of the palaces and sites of Sintra on our upcoming Insider Journey to Portugal, alongside expert art historian and horticulturist (and Indagare-favorite host) Amy Kupec Larue.