In the nineteenth century, the Portuguese royal family turned the tiny fishing village of Cascais into a resort, and in 2011 the titans of business brought international attention to the Portuguese Riviera by selecting it for the start of the 34th America’s Cup, one of the most prestigious and oldest yachting races in the world.
Not many North Americans visit Portugal, and when they do it’s usually just Lisbon. But just a half hour away, Cascais is a mixture of old-world charm and cosmopolitan restaurants and boutiques. Where else would you find peacocks roaming by colorful, modern outdoor art sculptures and millionaires sunbathing on yachts next to fisherman repairing nets on colorful wooden boats?
Old town is the place to stay. It’s easy to get lost in this area, with its twisted alleys and narrow streets, but getting lost is half the fun. Enjoy the pastel-colored villas built by nobility and lined with bougainvillea. Discover quirky museums such as the Museu do Mar (Museum of the Sea), displaying shipwreck remains, rare shells, and even fisherman’s boots!
It’s a great walking town, and Direita Street, filled with local shops, is closed to cars. If you walk to the end, you’ll find Camões Square, where free outdoor concerts are held during the summer months with fireworks every Saturday at midnight.
Traditional sidewalks, called calcada, made of small gray and white stones shaped like ocean waves, lead you past a sixteenth-century fortress to the pier where you can enjoy fresh seafood right off the boat, watch sailors unfurl spinnakers, and eavesdrop on lively fish auctions.
Strike up conversations with the locals and they’ll tell you that a Cascais native, Afonso Sanches, discovered America first in 1482. On the way home, according to the legend, he stopped at Christopher Columbus’s house in Madeira. Rumor has it Columbus discovered Sanches’s diary and repeated the trip.
Portuguese sailors brought back the best of Europe. O’Neill’s, an Irish pub, is one of the most popular restaurants in old town. For a splurge, try Fortaleza do Guincho, which was recently awarded a Michelin star. Save room for dessert; nuns created the recipes in the eighteenth century!
Work off your meal surfing, sailing, or windsurfing. Hikers will want to explore the nearby UNESCO heritage park in Sintra. Art lovers will appreciate the world-famous Paula Rego museum. Her feminist paintings of Portuguese society are housed in a peach-colored building shaped like a triangle that looks like it belongs in Egypt. The Museu Conde de Castro Guimarães, located across from the marina, showcases paintings and furniture from the early 1900s. Peacocks, chickens, and roosters stroll through the adjacent park and lend their sounds to the Cool Jazz Fest held on the grounds.
Those who consider fashion “wearable art” are in luck. Old town has frequent outdoor markets with locally handmade goods as well as designer boutiques selling everything from Vespa messenger bags to European bathing swimsuits that will make you feel like Brigitte Bardot.
Feeling lucky? Visit the Casino Estoril, one of the oldest and largest in Europe. Too smart to gamble? Stroll the lush gardens, attend one of the frequent free concerts, or visit during December, when the park is transformed into a winter scene straight out of a 1950s movie.
If you feel like exploring outside Cascais, enjoy a cocktail at an old railroad car transformed into a bar and then take the train or drive along winding roads overlooking white-sand beaches dotting the Estoril coast like a pearl necklace. With year-round moderate temperatures, friendly locals who speak English, and breathtaking scenery, Cascais the perfect place to for exploring or just finding yourself lying on the beach.