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Sintra, perched in the hills of Portugal's Lisbon coast, has drawn people to its cool, misty microclimate since antiquity, when Romans and Moors alike built retreats there to escape the summer heat. The town flourished under Portuguese royalty starting in the Middle Ages, with the Sintra National Palace serving as a royal residence from the 14th century onward, its distinctive twin conical chimneys still dominating the old town's skyline.

 

Sintra's romantic reputation grew in the 19th century when King Ferdinand II commissioned the whimsical Pena Palace, a riot of colorful towers and eclectic styles built atop a hilltop ruin, inspiring other aristocrats to build their own fantastical estates like Quinta da Regaleira and Monserrate Palace.

 

Lord Byron famously praised the town's beauty in his poetry, cementing its status as a Romantic-era destination, and in 1995 UNESCO designated Sintra's Cultural Landscape a World Heritage Site in recognition of its unique concentration of palaces, gardens, and forests.

 

Today it remains one of Portugal's most visited towns, its layered history spanning Moorish castles, royal palaces, and 19th-century romanticism all within a compact, walkable landscape.