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How to Spend 3 Days in Cascais, Portugal


Hand-crafted, luxury experiences curated by our team—speak to our concierge to learn more

By Niamh Walsh on 20th September 2023

The ultimate itinerary for a long-weekend escape to the captivating coastal town of Cascais, Portugal.

Portugal, with its rich history, stunning landscapes, and vibrant culture, has become a top destination for travellers seeking a luxurious getaway. Cascais, a charming coastal town just a short drive from Lisbon, is the perfect place to experience the best that Portugal has to offer in a compact, three-day weekend break. If you're wondering what to do in Cascais and how to make the most of your luxury escape, you're in for a treat. From the renowned Cool Jazz festival held each July, to exploring the coastline on e-bikes, we've curated a list of things to do in Cascais that will ensure an unforgettable experience.

Things to Do in Cascais

Day 1: Arrival and Relaxation

Start your luxury weekend in Cascais by booking a flight with TAP Air Portugal. TAP is known for its exceptional service and comfortable flights, ensuring you arrive in style and ready to start your adventure. The airline offers numerous routes to Lisbon, with convenient connections to Cascais. Upon arrival at Lisbon Airport, indulge in the comfort of a private transfer to Cascais, allowing you to soak in the breathtaking scenery along the way.

Your luxurious base in Cascais awaits at one of its upscale boutique hotels, like the iconic Grande Real Villa Itália Hotel & Spa, offering panoramic ocean views, an indulgent spa, and exquisite dining. Rejuvenate by the hotel pool or take a leisurely promenade along the Cascais waterfront, immersing yourself in the coastal elegance.

Treat your taste buds to a culinary masterpiece at a fine dining establishment such as Furnas do Guincho, boasting Michelin-starred chefs and unparalleled sea views. Conclude your evening with a tranquil beachfront stroll under the moonlight, savouring the gentle sound of waves.

Cacais, Portugal
Cacais, Portugal

Day 2: Cool Jazz Festival

Begin your day with a sumptuous breakfast at your hotel, featuring a delectable array of local and international delights. Immerse yourself in the cultural treasures of Cascais by exploring the historic old town, including visits to Santa Marta Lighthouse and Casa de Santa Maria. Wander the narrow streets, admiring the town's authentic charm. Delight in the vibrant atmosphere of Mercado da Vila, savouring gourmet cuisine and perusing unique local wares. Continue your cultural journey with a visit to the Condes de Castro Guimarães, an enchanting mansion set amid lush gardens overlooking the sea. Explore the Cascais Cultural Centre or nearby art museums, appreciating Portugal's rich heritage.

Cascais is known for its vibrant cultural scene, and if your visit aligns with the summer months, don't miss the internationally acclaimed Cool Jazz festival. Held at the Parque Marechal Carmona, this event features world-class jazz and contemporary music acts such as Lionel Richie and Van Morrison, in a stunning outdoor setting. Enjoy the music, savour delicious food and drinks, and soak up the atmosphere. Be sure to book your VIP tickets in advance to secure the best seats.

Lionel Richie performs at Chase Centre on September 08, 2023 in San Francisco, California. (Photo by Steve Jennings/Getty Images)
Lionel Richie performs at Chase Centre on September 08, 2023 in San Francisco, California. (Photo by Steve Jennings/Getty Images)

Day 3: E-Bike Tour and Beach Bliss

Embark on a thrilling e-bike tour of Cascais' stunning coastline, led by knowledgeable guides who reveal the area's natural beauty and history. The tour includes hidden coves, picturesque cliffs, and charming fishing villages. Spend the rest of your morning on the golden sands of Cascais' pristine beaches, such as Praia da Duquesa, where you can indulge in water sports or simply bask in the sun. Bid farewell to Cascais in style with a final gourmet dinner at a renowned restaurant like Fortaleza do Guincho, boasting a Michelin-starred dining experience with Atlantic views.

Boco do Inferno, a chasm located in the seaside cliffs of Cascais. The seawater has access to the deep bottom of the chasm and vigorously strikes its rocky walls, making it a popular tourist attraction.
Boco do Inferno, a chasm located in the seaside cliffs of Cascais. The seawater has access to the deep bottom of the chasm and vigorously strikes its rocky walls, making it a popular tourist attraction.

Departure Day: A Final Taste of Cascais

Before departing, savour your last morning in Cascais with a leisurely breakfast and perhaps one final beachfront stroll or a bit of souvenir shopping in the town centre. As you head back to Lisbon Airport for your flight home, carry with you the cherished memories of a truly luxurious and culturally enriching weekend escape in Cascais, Portugal.

Cascais offers a perfect blend of culture, relaxation, and natural beauty for a luxury weekend break. From the enchanting Cool Jazz festival held each July, to the scenic e-bike tour of the coastline, every moment in this coastal gem promises an unforgettable experience. So, pack your bags, book your flights with TAP Air Portugal, and immerse yourself in the charm of Cascais for an indulgent weekend escape.

Cascais Old Town
Cascais Old Town

If you have the fortunate opportunity to extend your visit, be sure to incorporate these additional destinations into your travel plans. Discover more about Cascais here:

  • Cascais Marina: As you arrive at Cascais Marina, you'll be greeted by the sight of luxurious yachts and a vibrant coastal atmosphere. Stroll along the marina's promenade, admire the boats, and consider enjoying a meal at one of the waterside restaurants to kick off your journey.

  • Beach Bliss: Spend a day at one of the many beautiful beaches Cascais has to offer. Praia da Duquesa, with its soft sands and crystal-clear waters, is a favourite beach among locals and visitors alike. Alternatively, surf schools dot the coast, making it easy to catch some waves if you're feeling adventurous.

Surfing big waves in Cascais
The impressive waves that draw surfers from around the globe to Cascais.

  • Cabo da Roca: Venture to Cabo da Roca, the westernmost point of the Portuguese coastline, and take in the breathtaking scenery. This rugged coastline, part of the Sintra-Cascais Natural Park, is dotted with dramatic cliffs and idyllic beaches like Praia da Rainha, known for its golden sands and crystal-clear waters.

  • Coastal Adventures: Embark on a sea cave exploration adventure along the Cascais coastline. Parque Marechal Carmona, just a short walk from the old town, serves as a starting point for boat tours that take you into the heart of this natural wonder.

  • Beyond Cascais: Consider taking day trips to nearby destinations in the Lisbon region. Explore the Sintra-Cascais Natural Park, known for its sand dunes and unique rock formations. Guincho Beach is a popular spot for its wind and water sports, and it was once a favourite of the Portuguese royal family during their summer residence.

Aerial view of Sintra
Aerial view of Sintra

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