Once the playground of luminaries such as poet Fernando Pessoa and the Portuguese royal family, Cascais (pronounced kush-kaish) is rich in a sense of whimsical charm and character. Replete with winding laneways, contemporary art museums, and a pedestrianized old town with plenty to see and eat, it’s no wonder Cascais is now – as it has been for decades – the destination of choice for beach-seeking lisboêtas.

You can reach this stunning destination in just 40 minutes from Lisbon’s Cais De Sodre train station, so this is a great choice for a fun day trip or even to add a few days on the stunning Portuguese Riviera.

Far from your average sleepy seaside town, Cascais is flanked by impressive mansions that were built by many of the noble families who set up shop around the time of the first railway in 1889. Grand yet understated, charismatic yet easy-going, this destination certainly impresses. Looking for something to do? Check out the marina while fishermen bring in their daily catch, and head over to one of the many local restaurants where you can score inexpensive seafood and wine.

Head over to the Boca do Inferno, where in 1930 the infamous occultist Aleister Crowley faked his own death. There’s no doubt about it, Cascais is a melting pot of history, where golden sands meet the turquoise ocean, and a rich past meets modern day marvellousness.

Deciding to forego the mid-summer rush of tourists we headed to Cascais in late April, which proved to be the perfect combination of mild breezes and bright blue skies. Although we experienced the odd rainy day, the crowds were manageable and the evenings peaceful.

One of the finest coast-side walks I’ve had the pleasure of strolling, the Cascais-Estoril promenade is perfect for sun-seekers, people-watchers and those who enjoy a peaceful wander with plenty to see.

With waves crashing over the side of the promenade you have to be careful to stay dry. However, the throngs of fishermen who line the pathways don’t seem to mind.

Even in April some courageous bathers braved the frigid Atlantic to enjoy a midday swim.

A sleepy fishing village no more, Cascais is now a playground for the rich and fabulous. Along with art galleries and museums, you’ll find luxury boutiques, fine dining and all-night bars that are sure to entice even the most discerning of travelers.

Wandering the surrounding streets you’ll find a mixture of “old meets new”. Street art signifies a new wave of artistic input, and a younger generation keen to make their mark on Portugal.

Walk along the Av. Rei Humberto II de Itália and you’ll stumble across the Casa de Santa Maria, an ocean-side villa built in 1901.

Beyond the Casa de Santa Maria you can also visit the seriously charming Santa Marta Lighthouse. Don’t forget your camera, as this spot has some of the best views of Cascais.

Further on from the lighthouse lies the Santa Marta Museum. Designed by the architectural firm Aires Mateus, this contemporary structure is juxtaposed eye-catchingly against the historic residence and offers a wonderful space to explore and discover.

Meandering back through the windy alleyways, it’s easy to feel as though you’ve traveled back in time.

Much like Lisbon, Cascais boasts the same beautifully tiled façades that add life, color and verve to their simple stone structures.

Back in the center, we’re surprised yet again to see another hidden beach. The Praia da Rainha is lined with jutting rocks and man-made walls, where locals come and cool off during the hot summer weather. Visiting in April definitely showed a different side of this usually busy coastal town, while offering a

sense of what Cascais might have felt like prior to the tourism boom. Although the water might have felt a little too chilly to brave, the scenery, food, wine, and culture certainly sufficed.