How to plan the ultimate trip to Cascais, the heart of the Portuguese Riviera

An important fishing town through the Middle Ages, an aristocrat holiday hotspot in the late 1800s and a safe haven for exiled European royalty in the Second World War — Cascais has lived many lives since its inception as a settlement for salting fish during Roman times. Today, reminders of this multifaceted history can be found both in the town itself and the wider area, such as in nearby Sintra.

The unhurried pace of life here is a distinct contrast to the constant hum of Lisbon, 18 miles to the east. Museums focusing on the region and its connection to the sea have found homes in the ornate 18th- and 19th-century mansions emblematic of the region, while the bounty of the Atlantic is celebrated at Cascais’s restaurants. Parks and gardens are woven through the town and beyond it there are lush mountains, wild beaches and hiking trails.

Benefitting from refreshing Atlantic breezes in summer, the town is a favoured destination for the Portuguese and especially residents of Lisbon — yet Cascais remains mostly hidden to foreign tourism. And unlike many resort towns and cities, it doesn’t lose its appeal — or its residents — outside of the summer.

Day 1: Museums & mansions

Morning
Start your day slowly, like the locals do, at the revamped 1950s marketplace Mercado da Vila, with a coffee and sweet pastry such as pastel de nata. There are dozens of produce stalls to peruse and excellent shops for souvenirs of the edible kind — handmade chocolates, artisanal cheeses and reds from the Lisbon wine region. On Wednesdays, a vintage market pops up next to the fruit stands, and during summer there’s live music and a rotating roster of street food stalls where you can buy lunch. Try anything with sardines, a staple of the region, and eat your food at the communal picnic tables while watching market life unfurl. On the outer wall of the market, look for the traditional azulejo tile mural, which recounts the history of the region.

Afternoon
From the market, swing past Cascais’s most photographed sight — the Italianate Casa de Santa Maria and adjacent blue-and-white striped lighthouse — en route to the Bairro dos Museus. The quarter is home to nine museums, all a short walk from each other, shining a spotlight on everything from local life to Portuguese culture. Start at the Museu da Vila, housed in a small but ornate 18th-century building. Inside, old photographs, ancient artefacts, music and film document the evolution of Cascais. Continue on to Museu do Mar, dedicated to the region’s maritime history, and finish with a visit to the Museu Condes de Castro Guimarães, for an insight into the life of the aristocrats who once spent summers here.

Evening
Eat at Jardim dos Frangos, a go-to for traditional Portuguese piri-piri chicken, in central Cascais, but save room for ice cream at Santini. It’s the oldest parlour in Portugal and still uses the original Italian family recipe from 1949. Afterwards, head across the street for a drink at either John Bull or Chequers. These institutions, opened by English and Irish expats, might look out of place in Cascais but have a historical connection to the town. During the Second World War, they became gathering places for the city’s international crowd, including exiles, refugees and Allied spies. Today they remain a great spot for a local pint and people-watching.

Day 2: Sailing & coastal hikes

Morning
Hire a solar-powered boat from the marina and spend the morning appreciating the Portuguese Riviera’s architecture from the water, keeping an eye out for dolphins and other marine life as you go. Many buildings are unique, taking influences from different time periods and geographical locations, including gothic, Islamic and Moorish elements. Heading east towards the town of Estoril, highlights include Casa Palmela, influenced by the neo-gothic mansions of England, and Palacete Seixas, an eclectic late 19th-century mansion. Once back on dry land, eat lunch the Portuguese way at Páteo do Petisco, ordering small sharing dishes of potato-peel chips, blood sausage and fried cuttlefish.

Afternoon
Cabo da Roca, a half-hour drive west of Cascais, is reachable by hire car or bus and makes a good starting point for exploring the wild western coast. The cliffs here tower more than 460ft above sea level, offering spectacular views out to the ocean, with the waves of the Atlantic crashing onto the rocks below. The Miradouro do Cabo da Roca monument marks the western edge of the continent. From here, you can amble along the coast or join the Praia da Ursa trail for a gentle, three-mile stroll to a viewpoint overlooking the remote Ursa Beach. Alternatively, take a challenging three-hour hike around the cape, which includes a descent to the windswept beach. If you’d rather do a guided walk, book with Walk Hike Portugal.

Evening
If you’ve hired a car, instead of rushing back to town, drive down the coast at sunset. Cliffs and crags give way to sand dunes and deserted beaches, and it’s especially scenic right before dusk when the landscape is painted golden. Once back in Cascais, take a loop around the town’s medieval fortifications to work up an appetite for dinner. The renovated square inside the fort hosts a contemporary art district with sculptures, statues and a small but excellent art gallery. Afterwards, bag a table at Taberna da Praça on the square. Its menu champions locally sourced ingredients and traditional dishes with a modern twist. Try the Portuguese fish stew caldeirada or steak with salty, cured Azeitão cheese.

Three more castle-palaces in Sintra

1. National Palace of Pena
The bright yellow, red and blue domes and turrets of the National Palace of Pena crown one of the peaks of the Sintra Mountains, high above the town. Built in the 19th century by Ferdinand II, the king consort to Queen Maria II, it’s one of Sintra’s most iconic sights and also one of the best examples of Portuguese architecture of the period. Contrasting architectural and decorative forms bring together gothic, Moorish and Islamic styles to create this dramatic romantic revival structure. Now a national monument and a UNESCO World Heritage Site since 1995, the palace is open to visitors — buy your ticket in advance and arrive either first thing in the morning or late in the afternoon to avoid crowds.

2. Sintra National Palace
The country’s oldest royal palace and also the only one to still feature structural elements from the 1200s, the Sintra National Palace is a journey through over a thousand years of Portuguese history and architecture. First references of the palace appear in the writings of 10th-century Moorish geographer Al-Bakrî and since then nearly every Portuguese king and queen has spent some time at the palace. The building has been shaped by different architectural influences, especially Mudejar style — a combination of Christian and Muslim art — but its most striking feature is the two tall, white chimneys. At over 100ft high, they connect to an equally impressive kitchen, which was built to prepare and cook game meat after royal hunts.

3. Park & Palace of Monserrate
This palace’s impressive pastel orange arches and ornately carved columns fuse Moorish revival and neo-gothic elements. An eclectic vision of the 19th-century British industrialist Francis Cook, the house and gardens represent the essence of Lisbon region’s summer architecture style, and the complex is much less visited than some of Sintra’s other palaces. Highlights of the house include the Music Room, with its ornate dome and excellent acoustics, and the curated gardens. In the latter, indigenous flora such as cork oak coexist with imported towering sequoias from North America, bamboo from Japan and ferns from New Zealand — it’s the perfect spot for a morning stroll or a lunchtime picnic.