City, Beach, and Castles---Lisbon, Cascais, and Sintra

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Advisor - Sydney Vaccaro
Curated By

Sydney Vaccaro

  • Arts & Culture

  • Beaches

  • Portugal

  • History

  • Local Culture

  • Bucket List

City, Beach, and Castles---Lisbon, Cascais, and Sintra
Curator’s statement

I had the amazing experience of visiting Lisbon at the end of May. This is the perfect combination of city, castles, and relaxing on the beach without renting a car. Lisbon is one of those cities that you get there and immediately think, “I could live here”. Everything is colorful and welcoming.

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What to Do in Lisbon

Take a TukTuk tour

Embark on a TukTuk adventure through Lisbon's charming streets. These three-wheeled vehicles may seem pretty “touristy”, but make sure you ride with a local, and they will give you an intimate and flexible way to explore the city, allowing you to navigate narrow alleys and discover hidden gems with the guidance of a local.

It’s also a great way to get acquainted with the city!

Spend an evening on a sailboat

Experience the magic of Lisbon from the water by spending an enchanting evening on a sailboat. Cruise along the Tagus River, witness the city lights, and enjoy a beautiful sunset.

Eat Portuguese pastries

Indulge your sweet tooth at Manteigaria, a renowned pastry shop in Lisbon. Known for its delectable pastries, especially the iconic pastel de nata. SO good!

Soak in the views and architecture:

Belem Tower: A medieval fortress on the Tagus River, Belem Tower offers stunning views of the river and the surrounding area. Explore its ramparts and enjoy a panoramic outlook.

Jeronimos Monastery: The Jeronimos Monastery has intricate architecture and is surrounded by beautifully landscaped gardens.

Castelo de S. Jorge: Perched on a hill, the Castle of São Jorge provides sweeping views of Lisbon. Explore the castle's towers and walls to see the city's layout.

Lisbon Cathedral: Visit Lisbon Cathedral, a historic church, and climb to its terrace to view Alfama and the city below.

Explore a museum

Discover Lisbon's rich cultural heritage by visiting a museum. The National Tile Museum (Museu Nacional do Azulejo) is a notable choice, showcasing Portugal's traditional tile.

Day Trips From Lisbon

Sintra: Sintra truly feels like a fairy tale wonderland, including lush gardens, mist, and colorful castles.

Palaces in the Clouds: The colorful Pena Palace, perched atop a hill, is a whimsical fantasy of turrets and terraces.

Enchanted Forests and Gardens: Delve into the mystical beauty of Sintra's parks and gardens. Stroll through the leafy paths of Pena Park, where exotic trees imported from all over the world grow and hidden follies create an otherworldly atmosphere. The gardens of Monserrate Palace are also a great place to go for this.


I’d actually recommend staying in Cascais for more than just a day here. I stayed at the Intercontinental Cascais-Estoril last time we went and it was amazing.

A Coastal Haven: Cascias, a charming seaside town with a laid-back vibe and amazing hotels. The best part is it's only a 30-minute drive/uber from Lisbon. It has natural rock formations where waves crash dramatically against the cliffs, such as the Boca do Inferno for even more amazing views.

Just relax

Relax on golden beaches, soak up some vitamin D, and eat lots of amazing fresh seafood

This trip is perfect if you are looking for something warm and relaxing, and does not have the stress of driving or renting a car. From the historic allure of Lisbon to the fairytale landscapes of Sintra and the coastal sun of Cascais, this trio is a perfect European gem.

Need to Know

Lisbon is the perfect vacation if you are looking to relax, get some sun, and also have some European charm with it.

This trip report is part of our ongoing series on travel to Portugal. In need of further inspiration? Check out Julia Garcia’s guide, Food & Drink Lovers Guide to Porto, Portugal.

Advisor - Sydney Vaccaro

Travel Advisor

Sydney Vaccaro

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