There are little pockets of odd, otherworldly beauty all over the world.  Not the natural otherworldly beauty of Tenerife's lunar landscape or Greece's Meteora, but manmade wonder, combinations of design and architecture that take you somewhere else. Port Merion in Wales, Gaudi's El Capricho in Comillas, Tanah Lot in Bali, they all fit where they are, but with a little imagination, you are transported somewhere else. Just outside of Lisbon you can find one such wonderland on our Walking Sintra to Cascais trip. 

In a Nutshell:

Where: Lisbon, the capital of Portugal, is situated at the mouth of the Tagus river, about a third of the way up the country. A 40-minute train ride towards the coast brings you to Sintra, where this tour starts.  From here you meander through the Sintra-Cascais Natural Park before exploring the Atlantic Coastline before heading down to finish in beautiful Cascais. 

Distance: The full walking distance on this route is 41miles which you would walk over 5 walking days. The first day is deceptively short, coming in at a mere 3 miles, however, you will end up walking a lot further as you sightsee the cluster of delights that Sintra holds. The rest of the days average about 9 miles walking, so plenty of time to relax and discover after your daily walk.   

Grade: While the distances are not huge, we have still graded this trip as Moderate. The route follows a mixture of gravel trails, forest and clifftop paths and daily ascents are between 270m and 540m, so if you have a decent level of fitness and have undertaken some long-distance walking in the past, you will have no problems on this trip. The trip is all loaded into the Macs App, so navigation is not even slightly an issue.  

Why Walk Here?

Sintra is simply outstanding. There are few places on earth that imbue this fairy tale essence, this dramatic escape to somewhere not of this dimension. Surrounded by lush green forests and set atop a hill, the town evokes images of isolation, of being cut off from the rest of the world. The heart of the fairytale is the stunning Palácio Nacional da Pena, whose vibrancy permeates the whole experience of visiting Sintra. It radiates beauty and joy and is not just a big colourful building, but an intensely intricate and well put together palace which is well worth exploring. 

Contrary to the glowing ethereal beauty of the Palace is the Quinta da Regaleira. An ornate gothic mansion with a brooding presence that can be felt as you walk towards it. This is basically where the bad guy lives in the fairytale of Sintra. Gothic and slightly creepy, but so intricately detailed and wonderful that it will likely be the highlight of your trip. With vast botanic gardens, all centred around a variety of stone towers, follies, wells and caves.  Littered with allusions to the world's great secret societies, the Quinta de Regaleira winding maze of gardens will take up much of your day.  

While there are many other places to visit in Sintra, the final one you should focus on is the Castelo dos Mouros, which snakes its way up to the highest point in Sintra.  Crumbling and ancient, but completely solid, you will be rewarded with incredible views from the top and it is well worth the gradual climb. 

After Sintra, your home for the following three nights will be in Azoia. Originally built in the 13th century, the Convento de Sao Saturnino Guesthouse has been lovingly restored from ancient ruins into an elegant hotel. With its labyrinthine interior and tranquil setting between the hills and the sea, your 3-night stay here will be a unique and unforgettable experience. Each room has open beams, antique furniture and its own special charm. The pool has superb views south to the sea and over the majestic Touro Valley. 

The walking leads you through a variety of terrains, from dense, lush forest, to impossibly high cliffs as you approach Cabo da Roca, Europe’s most westernmost point, past long stretches of golden sand, beaten by the relentless waves of the Atlantic.  Beach bars and tiny cafes provide great places to lunch or snack, whether it is the fresh, simple seafood or a simple pastel de nata and cup of very strong coffee. 

Cascais is your final destination and being one of the original European getaways for the wealthy (and alledged birthplace of sunbathing) you will enjoy the spectacular beaches, and laid back lifestyle that goes along with it. With little bars, cafes and restaurants, beautiful wide open squares lined with bright white buildings and azulejo tiles, Cascais is a place you can easily relax into. 

Planning and Preparation

To get to the Walking Sintra to Cascais trip, you simply fly into Lisbon.  From here you can take a 30-minute train out to Sintra and a similarly long one back from Cascais at the end. Nice and straightforward. 

If you have any questions about the route, don't hesitate to contact one of our Destination Specialists, who will be more than happy to help.