Portugal ranks as the sixth most popular pick for British holidaymakers – Peter Samson focuses on the destinations of Cascais and Lisbon 

Lead image: Cascais and Estoril area

Cascais, the crown jewel of the Portuguese Riviera, has long drawn royalty, aristocrats, and high society to its golden coastline. In the late 19th century, Portugal’s royal family began summering here, transforming a sleepy fishing village into a playground for Europe’s elite. 

Dubbed “the beach of the Court,” the town soon filled with opulent villas, refined hotels, and elegant seaside cafés.

The arrival of a coastal road and railway from Lisbon changed everything. A journey that once took five hours by carriage now took 40 minutes, making Cascais the ultimate getaway for Lisbon’s well-heeled and well-connected. 

Cascais Marina

The 007 Connection

During World War II, its reputation added intrigue: Ian Fleming drew inspiration from nearby Casino Estoril’s spy-laden social scene to write Casino Royale, and On Her Majesty’s Secret Service was later filmed in the area.

Even during wartime, glamour lingered. The exiled Duke and Duchess of Windsor stayed with a local banker, mingling with eccentric art collector Peggy Guggenheim and American performer, Josephine Baker. Today, the allure continues. Cristiano Ronaldo is reportedly building a multi-million-pound retirement retreat here, and the town remains a stylish haunt for the global elite.

Lisbon’s National Pantheon

A cosmopolitan hotspot

In 2025, Cascais is the perfect blend of past and present. Cobbled lanes, 19th-century mansions, and a 16th-century fortress sit harmoniously beside sleek marinas, luxury boutiques, and modern design. We stayed in a well-equipped apartment in the heart of the town and began exploring with a visit to the local museum, housed in a charming rococo-tiled building. Inside, a vivid exhibition charts Cascais’ journey from Roman outpost to cosmopolitan hotspot.

A particularly colourful display described the town’s golden age of the 20th century: “cocktail receptions, flirting, gala nights, and semi-Edenic nudism on the beach.” It sounded more glamorous than scandalous. That sense of breezy sophistication still lingers today—whether you’re enjoying seafood on the promenade or people-watching in a sun-drenched piazza.

One of Cascais’ Grand Villas

Cascais is a haven for food lovers. Visitors can indulge in fine seafood, tuck into flaky pastéis de nata, and relax in oceanfront cafés that offered a perfect view of the sunset and surfers catching the last wave of the day.

We used our time well, racking up steps along coastal trails. One direction took us west toward Cabo da Roca, the westernmost point of continental Europe. The other led us east through Estoril and to the Fort of Santo António da Barra, a 16th-century star-shaped fortress with a colourful history—from naval defence to prime ministerial holiday home. Now restored, it houses a museum and offers sweeping Atlantic views from its ramparts.

Forte Da Cruz

Sunset viewpoints are must-sees

Our winter escape, graced with blue skies and mild temperatures, ended with five nights in Lisbon. This was my fifth visit to the capital—and still, it surprised me. We based ourselves in Alfama, one of the city’s oldest neighbourhoods, where steep alleyways are lined with ceramic-tiled houses, boutiques, and family-run cafés. From here, we rode the iconic yellow No. 28 tram and explored São Jorge Castle, perched high above the terracotta rooftops.

No visit to Lisbon is complete without stopping at its miradouros—viewpoints scattered throughout the city. One afternoon, we paused at Miradouro da Graça with a glass of port in hand, watching the sun cast golden light over the hills. A quintessential Lisbon moment.

Lisbon’s Parque Eduardo VII

The city is a feast of architecture. From the grandeur of Jerónimos Monastery to the bold curves of the MAAT museum and the striking 25 de Abril Bridge, Lisbon dazzles at every turn. Praça do Comércio, the city’s grand riverside square, offers a perfect place to take it all in.

Before leaving, we visited the National Pantheon, home to the memorials to many famous sons and daughters of Portugal including the tomb of football legend Eusébio. Originally a 17th-century church, it was completed in 1966 and features a vast dome, marble interiors, and one of the best views over Alfama and the river.

While pastéis de nata became a naughty daily indulgence, it was the rich history, beauty, and elegance of Cascais and Lisbon that truly made the trip unforgettable. The eyes, as they say, had it.

Travel notes

Flights: EasyJet flies direct to Lisbon from Edinburgh.

Peter Stayed in Villa Sofia Cascais – from £94/night; Tandem Palacio Alfama Suites in Lisbon – from £90/night (both via Booking.com).

Transport: Cascais to Lisbon by train £3 or Uber £20