Sintra and Cascais

Hidden in plain sight, some of Portugal’s greatest treasures lie within a stone’s throw of Lisbon.

An hour’s drive from Lisbon, Sintra emerges, like an apparition, from a hilly forest. Sintra is a slightly surreal town of fantasy and magic, hidden messages, and Freemasonry.

With your expert guide to interpret sign and symbol, legend and lore, wander in thrall through enormous palaces – playgrounds for the royal (and other) eccentrics of Portugal. These palaces of veiled secrets are lavish jumbles of Moorish ruins, swan-filled lakes, gargoyles, grottoes, secret passages, hidden staircases, and Gothic towers.

Perhaps the most lavish conceit of all is the delectable Pena Palace – a pastel-hued hilltop pastiche of every conceivable style of architecture that embodies the eccentricity of Sintra.

Of course, we have our trade secrets just as the freemasons had theirs. We’ll show you a very special little tea house, a surprising art museum, and the perfect 19th century place for lunch.

On a clear day, you can see from the heights of Sintra to the Atlantic and to a series of old-world European seaside resorts, once the retreat of the privileged classes of Europe. Today they invite those who love sailing (world championships have been held here), windsurfing, enjoying the sand and ocean, or soaking in the ambience of summer evenings.

Cascais, small in size, offers Portugal’s best people-watching. Favored by the Portuguese as a summertime retreat, it retains both an authentic charm and a bustling seasonal buzz. Straddling three small bays with craggy rocks and small sand beaches, its colorful fishing boats set out every morning to fetch your dinner, served at some of Portugal’s best seafood restaurants.

The palm-lined promenades of neighboring Estoril, a 30-minute walk from Cascais, recall a bygone era. With one of Europe’s great 19th century hotels, famous as the setting for James Bond’s “Casino Royale,” it is a magnet for World War II history buffs. Portugal was neutral and ideally located for spiriting people out of war-torn Europe, and Estoril was a meeting ground and listening post full of international spies, counter-spies, couriers, and freedom fighters of the Resistance.

Perhaps the most romantic (and our favorite) way to arrive in Cascais or Estoril is by private boat from Lisbon. Begin your journey at the very spot from which Vasco da Gama set out, marking the start of Portugal’s era of maritime glory.