For the 50+ Traveler
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Cascais, Portugal, located about 25 minutes west of Lisbon, was a glorious surprise. I had never been to Portugal before. When I arrived at the Lisbon airport, I hopped into a cab and headed to my hotel in Cascais. I checked in, walked into my room, and opened the patio door of my room to see one breathtaking view of the beach.

Cascais is so much more than a beach resort, as gorgeous as the beaches are. It is a charming all-season small town, with cobbled streets, beautiful villas, several museums, a historic center, a plethora of hotels and restaurants, and some of the most pleasant people I’ve encountered as a tourist abroad.

King Luis I, whose reign began in the mid-19th century, built his summer home in the Citadela (formerly a 15th-century fort) in Cascais in 1870. Within 50 years, the railroad from Lisbon to Cascais was bringing moneyed visitors to the town. During World War II, Cascais and neighboring Estoril became the destination for wealthy exiles escaping danger from all over Europe. Now locals, expats, and tourists crowd the narrow streets and the beaches.

Casa das Historias Paula Rego in Cascais.
Barbara Winard

What To Do In Cascais

Before you do anything, learn to pronounce Cascais. The closest I came was kash-kie-sssh. As for pronouncing other words in Portuguese, my advice is ask questions and try, try again. Cascalenses, the people who live here, will appreciate your efforts. Most speak English as well.

1. Wander Around Town

Cascais is simply a charming place to explore. Because it is a popular day trip from Lisbon, perhaps the best time to go is early in the morning, when the scenic path along the water is not yet filled with walkers, bikers, and joggers. Watch your step on the cobblestoned streets, though; they can be slippery in bad weather.

2. Visit Museums

My favorite museum in Cascais was Casa das Historias Paula Rego, which features the diverse creations of this famous Portuguese-born visual artist. The striking pyramid-shaped building housing her art was designed by noted architect Eduardo Souto de Moura. Schedule about 40 minutes to see the collection.

Praia da Conceicao in Cascais.

3. Take A Welcome Break At A Park

The Marechal Carmona Park is just across the street from the Paula Rego museum. Inside the park, you’ll find a snack bar, a little bridge over a small lake -- which is populated by enthusiastic turtles -- and a small zoo, plus benches to sit and watch folks enjoying nature.

4. Visit The Beaches

Walk the beachfront promenade from Cascais to Estoril and check out the beaches within walking distance of the historic center of Cascais: Praia (beach) da Conceicao, Praia da Duquesa, Praia da Rainha (especially scenic and near the center of Cascais), and Praia da Ribeira (also called Fisherman’s Beach), which is closest to old Cascais. About a half-hour walk away is Praia do Guincho, a popular surfing center.

5. Visit The Market

The Mercado da Vila is a giant structure filled with everything from the freshest fruits and vegetables to flowers and cheese to meat and fish (but no cod because the most popular fish in Portugal -- source of the ubiquitous bacalhau dish -- is not local; it has actually been imported from colder waters since the Age of Discovery starting in the 15th century).

The Boca do Inferno in Cascais.

6. Visit The Boca Do Inferno

Just a few minutes from town along the coast road, Boca do Inferno (Hell’s Mouth) is where many locals and tourists go to watch the sunset with the sound of waves crashing against the cliff face.

7. Check Out The Sidewalks

With their traditional Portuguese black-and-white stone mosaic (called calcada), the streets are truly distinctive. Many of the houses in Cascais are still inhabited by the original families. Some of the most charming streets include Rua do Gama, Rua Tenente Valadim, and Rua Fernandes Thomas.

8. See A Fado Performance

Although most of the best fado performances are in Lisbon or Coimbra, Cascais still has a few places to eat and listen to what many consider the soul music of Portugal. Locals use saudade, or “longing,” to describe the feeling of the music.

Cais 16 Craft Gallery in Cascais.

Where To Shop

Souvenir and food shops are all over Cascais, but there are several places to buy art or crafts in town as well, including:

Cais 16 Craft Gallery

This charming shop also carries distinctive jewelry.

Zazule

Zazule will print your photographs on tiles. The popular glazed ceramic tiles (azulejos) can be found on buildings all over Cascais (and all over Portugal). If you purchase a tile from a shop, make sure that claims of value and history are proven.

A table at Mar do Inferno in Cascais.

Where To Eat

Cascais is known for its seafood, most of it fresh off the fishing boats lining the harbor. Don’t worry if you’re a vegetarian, though; there are a number of restaurants and cafes catering to you, too.

Mar Do Inferno

Called “one of the best fish restaurants in Cascais,” Mar do Inferno has the best view from atop the cliffs, located near the Boca do Inferno. Choose from giant platters of grilled seafood, including scallops, oysters, sea bass, shrimp, lobster, mussels, and octopus.

5 Sentidos

Located in town between the Centro Cultural de Cascais and Casa das Historias Paula Rego, 5 Sentidos is popular with tourists and expats alike; both come for meat and seafood dishes. The restaurant also offers live music on weekends.

Cafe Galeria House of Wonders

A vegetarian favorite that serves tasty mezze as well as juices and smoothies, pastries, and vegan desserts, Cafe Galeria House of Wonders features a rooftop sea view from the heart of historic Cascais, up several flights of stairs.

Views from the Pousada de Cascais.
Barbara Winard

Where To Stay

Pousada De Cascais

Through the centuries this building served as a citadel to protect the town against pirates. The Pousada de Cascais became a royal residence, a presidential palace, and then a military base. A 126-room luxury hotel opened on the site in 2012.

Fortaleza Do Guincho

The Fortaleza began as a 17th-century fortress. You can hear the waves crash beneath you from any of the 27 rooms in this Relais and Chateau dwelling, located atop a cliff. The hotel is also near the lighthouse of Cabo da Roca, Europe’s westernmost point. One of the first places in Portugal to win a Michelin star, the hotel’s restaurant opened in 1998 with a French menu but now serves mostly Portuguese food.

Pergola House

The adults-only Pergola House is a Mediterranean-style mansion with elegant white marble floors and staircases. It is located in the heart of Cascais and has only ten rooms. The building and the beautiful gardens have belonged to the same family for more than 100 years.

Casa Vela Guest House

Casa Vela Guest House is located on a quiet street in the town, as well. Surrounded by gardens and a large swimming pool, this guest house has 15 rooms and suites, each named after a location or a spice discovered by the Portuguese in the 16th century, with themed colors and matching accessories.

Travel Tips

When To Visit

The most popular times to visit Cascais are from Easter until October, with most people visiting in July and August. But even in the coldest months, surfers line the beaches, and the town is filled with people strolling. I was there for a week in February, and every single day was sunny and in the 60s and low 70s. It was perfection.

The town of Estoril near Cascais.

Places To Visit Near Cascais

Estoril

A 10-minute drive from Cascais (and on the way to Sintra), Estoril is a sophisticated vacation destination called, by some, the Portuguese Riviera. The Estoril casino welcomed exiled royalty and deposed despots alike during World War II, as well as spies from both sides.

Sintra

Described as a wedding cake, Disneyland for adults, a fairy-tale castle -- or a slightly drugged dream -- Pena palace in Sintra is a UNESCO World Heritage Site, the creation of King Consort Fernando II of Saxe Coburg, husband of Queen Maria of Portugal. The palace was completed in 1854 and built on a 16th-century monastery largely destroyed in the Lisbon earthquake of 1755. While the palace is inspiring from a distance, seeing it up close, with its turrets and bold colors, is dizzying. Note: People with mobility issues can take the shuttle going up the side of the hill.

Mafra

Built in the 18th century by order of King Joao V, the National Palace of Mafra is considered the most important baroque monument in Portugal. It was proclaimed a UNESCO World Heritage Site in 2019. Just 35 minutes by car from Cascais, the building contains a library (with 36,000 books dating from the 14th to 19th centuries, down from 60,000 at its height) and is thought to be one of the most beautiful in the world. Plan on at least an hour to tour the palace and library.

Inspired? If yes, read up on Portugal: the best things to see and do after 50.

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