Covered in elegant pine trees, the painterly hills of the Serra de Sintra in Portugal boast a fabled, historic mountain town that is also a UNESCO World Heritage Site. Known simply as Sintra, the destination attracts both day-trippers from Lisbon escaping the stifle of the metropolis, and international visitors who come to soak up its storied charm. The town is reminiscent of a Hans Christian Andersen fairytale: Everywhere, there are architectural marvels in the shape of palaces and castles, as well as some of Europe’s finest resorts and hotels.
Known as the country’s foremost center of Romantic architecture, Sintra is unapologetically eclectic, with well-preserved Gothic, Egyptian Revival, Moorish and Renaissance buildings. Kings of Portugal loved the cool crisp air of the mountains here and the gardens of luxuriant white and pink camellia blossoms, and the poet Lord Byron penned his narrative poem Childe Harold’s Pilgrimage after being inspired by the town.
The blend of cultures is disarming. You’ll see vestiges of Portuguese royalty and Moorish princes and princesses who resided here, adding to the town’s layered and textured history, and architectural marvels like the Palácio e Quinta da Regaleira, completed in 1910, known for its magical gardens. It is this charming mixture of styles that makes this destination unique, mysterious and adored.
From the Palácio Nacional de Sintra—the beating heart of the town, with its unmistakable conical chimneys—to the ruins of the 8th century Castelo dos Mouros (Castle of the Moors), and the majestic amber and pink Palácio Nacional da Pena, the town’s key attractions are numerous and unforgettable.
Art historian Estela Mendes was born and raised in Lisbon and has worked in national palaces throughout Portugal. She currently leads tours to Sintra for Context Travel and for her, the town’s charms are “its enchanting architecture, particular microclimate, and very lush vegetation.” The cuisine is also notable: Regional pastries like the travesseiro (a puff pastry with rich cream) and the queijada (a custard-like cupcake made of milk and egg) are a must, and the Colares wines of the Atlantic coast are not to be missed.
It is not uncommon to try to cover Sintra in a day, but that is ambitious. Patricia Serrano, who runs travel website FreshTraveler, has ventured to Sintra from Lisbon by pedicab just to admire the medieval architecture and its surroundings—“the ruins of the Castelo dos Mouros stand high above Sintra with beautiful views,”—but she notes you can easily spend a few days exploring all the sights of this historic spot instead of trying to cram it all into 24 hours.
No visit to Sintra is complete without taking in the Palácio Nacional da Pena, high atop a cliff: It might well be the most impressive of the town’s attractions, with its vividly painted walls and amalgamation of styles ranging from North African to medieval Gothic. It was commissioned around 1840 by King Ferdinand II, who wanted it to resemble a scene from an opera and transformed it from monastic ruins into a fabulous palace that served as a summer residence for the Portuguese royal family. Engineer Wilhelm Ludwig von Eschwege helped oversee the project, inspired in part by the German castles along the Rhine. Visitors will marvel at the palace’s Moorish arches, stucco walls, and clock tower, as well as its splendid Islamic and medieval elements, including ornate stained-glass windows.
Photographer and brand strategist Uma Muthuraaman, visiting the town with her family from Zurich, loved the bright yellow and red facade of the Pena palace: “It loomed over us like a dazzling jewel and remains our most memorable image of Sintra.”
“Pena introduced Revival architecture to Portugal in the 1840s,” explains Mendes. “By reviving architectural styles of the past, the palace tells the history of Portugal through its design.” She draws particular attention to features such as a chapel altar dating back to the 16th century, and the detailing on the walls of the king’s bedroom—similar to the ceiling of the chapel in the Palácio Nacional de Sintra.
Affectionately known to locals as the Paço Real, the stunning Palácio Nacional de Sintra, with its white conical chimneys, also has its roots in royalty. It is Sintra’s oldest palace: Initially constructed in the Middle Ages by the Moors, it was subsequently rebuilt and enlarged by successive Portuguese monarchs, including João I in the 14th century. Not unlike Versailles, it sprawls over several floors and is filled with treasures like the Swan Room, replete with graceful painted swans on the ceiling. The pièce de résistance in this beautiful palace may well be the Sala dos Brasões, a domed room whose ceiling and walls glitter with azulejo tiles: It showcases the coats of arms of King Manuel I, his children, and 72 noble households.
Only a few hundred feet away, the Castelo dos Mouros, situated on a hill opposite the Pena palace, is a beautiful set of ruins that date back to the Moorish rule of the 8th century. A small museum of artefacts found in the ruins is located on site, but the sheer beauty of the castle, with its turrets and walls, is a treat in itself (and perfect for that Instagram selfie).
A more recent architectural gem is La Quinta da Regaleira, a regal home with gardens to rival those of any palace. Especially popular with visitors is the larger of two swirling, mossy Initiation Wells, with its winding staircase seemingly plucked from the pages of The Lord of the Rings. The Quinta was built in the late 1800s by architect Luigi Manini, at the behest of António Augusto Carvalho Monteiro.
Muthuraaman found the gardens of Quinta da Regaleira wild and alluring: “[They] had many elements of a royal garden, like ponds, statues, and fountains, but the highlight was definitely the grottos! Every square inch of this garden felt surreal. We thought we were being led into a movie set, portraying a different era and time—untouched by humans.”
If you’re trying to choose lodgings in this town of just over 370,000 people, there are a number of luxe places to perch. One option is Penha Longa Resort, set within a protected 545-acre national park in the southern Sintra mountains. The Ritz-Carlton property—whose name means “Long Rock”—has historic roots: Originally founded as a monastery in the 14th century, it was transformed in the 19th century into a palace retreat for the royal family of Portugal. You won’t be at a loss for recreation in this resort, replete with nine restaurants (it is the only European resort with three onsite Michelin-starred restaurants) and two championship golf courses that wrap around a forest. The Historical Circuit on the premises is a favorite among guests, notes the resort manager. “It combines rich history dating back to the 14th century with a walk in the nature reserve.”
But if residing in an 18th century palace tickles your fancy, it can become a reality at Tivoli Palácio de Seteais, which became a hotel in 1955. Its 30 rooms, decorated with ornate furnishings and beautiful upholstery, are decidedly cinematic, and the hotel’s ballrooms are filled with frescoes and tapestries. With views of both the Castelo dos Mouros and the Palácio Nacional da Pena, the hotel also boasts beautiful gardens with more than 20 lemon trees as well as vegetables and herbs—all of which are regularly sourced by the hotel’s chefs. Little wonder, then, that prior guests have included Agatha Christie, Maria Callas, David Bowie and Brad Pitt.
Many travelers to Sintra also make a stop in Cascais, about 10 miles away. An ideal spot for families is Martinhal Cascais, with 12 two-bedroom villas and 72 spacious rooms. Founder Chitra Stern says that the resort attracts many families who want to escape the crowds of Lisbon.
While most visitors to this fabled corner of the world take tours on foot or by car, there are more singular options available. American ultramarathon runner Dean Karnazes found the town so inspiring that he coaxed his friend Peter Cooper to start giving running tours. “A few hundred meters from the town and you are on trails that crisscross the Serra, passing through mossy arches of vegetation and stands of pine, sequoia, camellia, ginkgo, fuchsia, and strawberry trees which, when in season, provide a great on-the-run snack!” he says. “Running in Sintra is like disappearing into a fairytale world.”
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