Sintra is a town of 18,000 inhabitants in the Serra de Sintra hills 25 km northwest of Lisbon — the UNESCO World Heritage "Cultural Landscape of Sintra" (designated 1995, covering the town, the palaces, the parks and the surrounding natural area) that the 19th-century Romantic movement turned into the most concentrated collection of fantasy palace architecture in Europe. Sintra was the Portuguese royal summer residence from the 8th century (the Moorish occupation) through the 20th century, and the clifftop and hilltop estates above the town became the site of an extraordinary experiment in Romantic architecture: aristocrats and monarchs competing to build the most spectacular, eclectic and fantastical palace or garden in the forested hills. The result is a collection of palaces and gardens without parallel in Europe: the Pena Palace (1842-1854 — the polychrome Romantic fairy-tale palace of King Ferdinand II of Portugal, built on the ruins of a Hieronymite monastery on the highest peak of the Serra, combining Manueline Gothic, Moorish, Renaissance and Baroque elements in a completely invented style coloured in deep yellow and red-terracotta; the most photographed building in Portugal); the Sintra National Palace (the Paço Real — the only surviving medieval royal palace in Portugal, with the extraordinary conical twin chimneys that rise 33 m from the kitchen and define the Sintra town skyline; the palace has been a royal residence since the Moorish period); the Quinta da Regaleira (the 1904-1910 estate of the millionaire António Augusto Carvalho Monteiro, designed by the Italian architect Luigi Manini with a Gothic-Manueline-Masonic aesthetic; the Initiation Well is the most extraordinary architectural feature — a spiralling underground tower descending 27 m with nine landings representing the nine circles of Hell in Dante's Inferno, accessible from the bottom via a subterranean tunnel); and the Moorish Castle (the 8th-10th century Islamic fortification on the Serra ridge, with the ramparts visible from the Pena Palace) and the Monserrate Palace (the orientalist fantasy palace of the English collector Sir Francis Cook, 1858-1869, with the Moorish dome, the Gothic arches and the Indian pavilion combined in the most eclectic single building in Sintra).
The Pena Palace (Palácio da Pena — the palace built 1842-1854 by King Ferdinand II of Portugal (Ferdinand of Saxe-Coburg and Gotha, cousin of Prince Albert of England; husband of Queen Maria II of Portugal) on the 534 m peak of the Serra de Sintra; the palace is built on the ruins of the Nossa Senhora da Pena Hieronymite monastery (destroyed in the 1755 Lisbon earthquake); Ferdinand hired the German architect Wilhelm Ludwig von Eschwege to design a palace that would combine all historical styles into a new Romantic synthesis; the result: the yellow and terracotta towers, the Manueline arch (a direct copy of the famous Manueline arch from the ruined monastery), the Triton Arch (with the 16th-century sea monster sculpture), the Arab Room, the Arab Hall, the Queen's bedroom with the original 1850s furniture; the most visited building in Portugal after the Jerónimos Monastery).
🎫 Book tickets via GetYourGuideThe Moorish Castle (Castelo dos Mouros — the 8th-10th century Islamic fortification on the Serra de Sintra ridge, commanding the approach from the Atlantic coast; the castle was built by the Moors to defend the Sintra territory from the north; captured by Afonso Henriques, the first King of Portugal, in 1147; the ramparts (the original Moorish defensive walls, largely preserved to their original height) wind along the ridge for 450 m between four towers; the view from the highest point of the ramparts encompasses the Sintra valley (with the twin chimneys of the Sintra National Palace visible below), the Pena Palace on the adjacent peak and — on clear days — the Atlantic Ocean and the Costa do Estoril; King Ferdinand II restored and romanticised the castle in the 19th century alongside his Pena Palace construction above).
🎫 Book tickets via GetYourGuideThe Sintra National Palace (Palácio Nacional de Sintra — the Paço Real; the only surviving medieval royal palace in Portugal still in its original location; the twin conical chimneys rising 33 m from the kitchen are the most recognisable element of the Sintra town skyline; built over a Moorish palace from the 8th-10th century, with major construction under King João I (1385-1433) and King Manuel I (1495-1521); the interior: the Swan Room (the ceiling painted with 27 swans — one for each lady-in-waiting of Queen Philippa of Lancaster); the Magpie Room (136 magpies, each holding a scroll reading "por bem" (for good) — allegedly painted as a response to a courtier kissing a lady-in-waiting that the king tried to excuse with the phrase "por bem"); the Arab Room (the finest Moorish tilework surviving in a Portuguese royal building, with the 15th-century azulejo tilework panels).
🎫 Book tickets via GetYourGuideSintra town centre (the village below the palaces — the cobblestone main street with the Piriquita bakery (the original 1862 Sintra pastry shop famous for the travesseiro (the "pillow" pastry — a puff pastry pillow filled with almond and egg cream, the specific Sintra pastry that defines the local confectionery tradition; available only in Sintra and impossible to replicate properly anywhere else due to the specific local almond variety used) and the queijadas de Sintra (the small pastry shells filled with fresh cheese, sugar, eggs and cinnamon — the classic Sintra confection recorded since the 14th century)); the Sintra central market; the view of the twin chimneys from the town square.
Quinta da Regaleira (the estate of António Augusto Carvalho Monteiro, 1904-1910 — designed by the Italian theatrical architect Luigi Manini with a programme of Gothic-Manueline-Romanesque-Renaissance-Masonic symbolism throughout; the palace, the chapel, the gardens and the underground tunnels create the most complex symbolic programme of any private garden in Portugal; the Initiation Well (Poço Iniciático — the underground tower descending 27 m through 9 spiral staircases to the bottom, with 9 landings representing the 9 circles of Dante's Hell or the 9 levels of Masonic initiation (Carvalho Monteiro was a senior Freemason); accessible from the bottom through underground tunnels that connect to the Tarot Tower and the water features of the garden; the Gothic chapel with the Masonic floor labyrinth; the tower with the serpent carved in Manueline style).
🎫 Book tickets via GetYourGuideMonserrate Palace (the orientalist estate 3 km west of Sintra — the palace built 1858-1869 for Sir Francis Cook (1st Baronet Cook — the English textile merchant and art collector who assembled the largest private art collection in England at Doughty House, Richmond); the palace combines a Moorish dome (modelled on the Alhambra), a Gothic entrance porch (modelled on Bath Abbey), and an Indian pavilion in a synthesis that no stylistic label can adequately describe; the gardens (designed by William Stockdale with the assistance of William Beckford's original 1790s garden as the basis — the same Beckford who built Fonthill Abbey in Wiltshire) contain plants from Brazil, Mexico, Australia and South Africa and are one of the finest Victorian-era botanical gardens in Europe; the water cascade system (the underground water tunnels supplying the garden fountains is a Victorian engineering marvel).
🎫 Book tickets via GetYourGuideCabo da Roca (12 km west of Sintra — the 140 m cliff promontory jutting into the Atlantic that marks the westernmost point of the European continent (9°30'57" W); the lighthouse (1772 — one of the oldest in Portugal); the stone monument with the Camões quotation ("Where the land ends and the sea begins" — from Os Lusíadas, the 1572 national epic poem of Portugal by Luís de Camões, which celebrates Vasco da Gama's 1497-1499 voyage around Africa to India); the Atlantic swell against the cliff base in winter and spring is the most dramatic coastal scenery near Lisbon; the certificate (a "Certificate of Presence at the Westernmost Point of Continental Europe" is issued at the tourist office for €11 — possibly the most earnest tourist souvenir in Portugal); the light quality at Cabo da Roca in the late afternoon, with the sun low over the Atlantic, is extraordinary for photography).
🎫 Book tickets via GetYourGuideCascais (15 km south of Cabo da Roca along the Costa do Estoril — the fishing village that became the summer resort of the Portuguese aristocracy when King Luís I made it the royal summer residence in 1870; the Cascais town centre has the finest concentration of 19th-century aristocratic architecture in coastal Portugal (the Casa das Histórias Paula Rego — the museum in the striking red concrete building designed by Eduardo Souto de Moura, housing the complete works of Portuguese-British artist Paula Rego; the Citadel (the 17th-century fortress converted into the Citadel Art Hotel); the Boca do Inferno (the "Mouth of Hell" — the natural sea arch 2 km west of Cascais, where the Atlantic swell crashes into the cliff cavity; the finest natural sea arch in the Lisbon region); the fresh fish restaurants of the Cascais harbour (the linguado (Dover sole), the rodovalho (turbot) and the percebes (barnacles — the most valued shellfish in Portugal)).
The Jerónimos Monastery (Mosteiro dos Jerónimos, Belém, Lisbon — 25 min from Sintra by train; UNESCO World Heritage 1983; built 1501-1572 in the Manueline style (the specifically Portuguese Gothic style named after King Manuel I, characterised by maritime and navigation symbolism: ropes, coral, seaweed, armillary spheres, the cross of the Order of Christ carved into every surface); the most significant single building in Portugal; built to commemorate Vasco da Gama's 1497-1499 voyage to India (the first direct sea route from Europe to Asia, the most significant navigational achievement of the Age of Discovery); the south portal (the most elaborate Manueline stone carving in existence — every cm of the 32 m portal is carved with saints, apostles, navigation instruments and maritime flora); the tomb of Vasco da Gama in the church.
🎫 Book tickets via GetYourGuideThe Belém Tower (Torre de Belém — the 1516 Manueline tower built in the Tagus estuary as a ceremonial gateway and river fortress; the Manueline ornamentation (the rhinoceros on the northwest bastion — the first carved stone rhinoceros in Western art, added after Manuel I received a live Indian rhinoceros as a gift from the Sultan of Gujarat in 1515 and re-gifted it to the Pope; the rhino drowned in a shipwreck off the Italian coast before arriving; Dürer drew a famous engraving of it from description); the Pastel de Nata at the Pastéis de Belém bakery (100 m from the Jerónimos Monastery — the original custard tart bakery, operating since 1837, using the original 19th-century recipe; the Pastel de Nata de Belém is legally distinct from all other Portuguese custard tarts; the queue is always long but moves quickly; the tarts are best eaten immediately, hot, with cinnamon).
🎫 Book tickets via GetYourGuideAlfama (the Moorish quarter of Lisbon — the only neighbourhood that survived the 1755 earthquake and tsunami largely intact (the earthquake of November 1, 1755, 8.5-9.0 magnitude, the largest in European recorded history, destroyed 85% of Lisbon; the Alfama district on the hillside was protected from the tsunami by the hill itself); the narrow streets, the white-tiled facades, the laundry lines, the Fado music (the Portuguese blues, UNESCO Intangible Heritage — the Alfama is the birth district of Fado; the most authentic Fado houses are in the Alfama (Tasca do Chico, Mesa de Frades) and operate from 8pm; the Fado is sung by a solo voice (fadista), accompanied by the Portuguese guitar (the 12-string teardrop-shaped guitar unique to Portugal) and the viola baixo; the standard emotional range of Fado is saudade — the specifically Portuguese emotion of longing for something absent or irrecoverable).
🎫 Book tickets via GetYourGuideTram 28 (the historic yellow electric tram (eléctrico) of Lisbon, operating since 1930 on the narrow-gauge route through the steepest streets of the Alfama, Mouraria, Graça, Estrela and Chiado neighbourhoods — the most atmospheric city tram ride in Europe; the tram climbs streets that would be impassable by car (the Calçada de São Vicente gradient is 12%); the Chiado neighbourhood (the intellectual and café district of Lisbon: the A Brasileira café where Fernando Pessoa sat and wrote (the bronze statue of Pessoa at the table outside); the Livraria Bertrand (founded 1732 — the oldest operating bookshop in the world); the Largo do Chiado square; the evening petisco (the Portuguese tapas culture of small plates of seasonal cured meats, cheeses, grilled fish and bread)).