Walking Portugal: Cascais to Sintra
- Zak Goldstein
- Nov 24
- 12 min read
A great walking holiday for Portugal fans. This multi-day trek takes you through costal bits, towns with amazing restaurants and the beautiful UNESCO World Heritage site of Sintra.
DINK Details
A lighter fare walking holiday with two must see Portuguese towns.
Season: March Time: 3 - 4 Days Difficulty: Some elevation but safe. | Highlights: - Castles and views - Seafood! |
Transportation (from Lisbon): - Train (1h)¹ - Walk (8h)² | Plan Ahead: - Book Sintra activities ahead of time. - English and Portuguese spoken. - Do NOT drive to Sintra |
1. To both Cascais and Sintra.
2. There is a maintained walking / bike path all the way to Cascais .
How are they able to give me this much lobster and wine??
Why Walk Cascais to Sintra
1) Portugal
We love Portugal. The food, the people, the nature; and it all pairs well with a douro or port wine. This area has many seafood restaurants, coasts, great towns, parks, and a UNESCO Heritage site.
2) The Season
With New Year's week off, the Cascais / Sintra region was perfect. Sintra is usually packed in season but not during the winter months. It might be too chilly for the beach but is now perfect walking weather.
3) Easier Walking Holiday
There was a desire to take it easier this walking holiday and this plan had shorter walking days and less hills. This was much more relaxing and hit the spot.
Getting There
Getting to the start at Cascais from Lisbon is very easy. We took the train but there is a decent walking trail as well. If you are spending some time in Cascais, know the only grocery store is in the train station, and it’s pretty small.
Train
It's a quick ride from Cais do Sodre station in Lisbon to Cascais. We bought tickets moments before boarding and there were plenty of seats.
Price: Around 2.5 euro
Time: 40m ride
Tap: Purchased from machine, didn’t see a tap and pay option
Walking Path to Cascais
We did not go this route but you can see a walking path run the entire way along the train. If you have an extra day, walking to Cascais it “appears” to be very doable. There are also many bike rentals and scooter rentals along portions of this path (so feel free to mix it up).
The DINK Plan
Day 0 - Cascais
A relaxing town with beaches, parks, and great food. Since it is close New Year's, most Portuguese towns have set up holiday shopping villages (and if you are lucky, a ferris wheel).
We walked around the Fortress Nossa Senhora da Luz de Cascais and Parque Marechal Carmona, which sadly had the Museu Condes de Castro Guimarães closed. The residential part of town was very cute with tiny cobblestone streets and cozy homes.
Bites
We stopped for lunch in the "hiper" food district with La Contessa Carpaccio House (because I have a carpaccio problem) and this place delivered. Places on our list we could not hit up were Taberna Clandestina Cascais (closed for holiday) and Izakaya Cascais (full up!, book ahead of time.) Both had amazing reviews and we will have to come back.
After a bit of a break, we headed back up to the dining district and hit up Asian Papa! Very good food with flavorful spice and fancy cocktails!
Stay - Hotel Baía
To start our journey, we splurged for one of the fancier hotels with a balcony overlooking the water. Our evening was spent playing our portable Azule board game while watching people enjoy the holiday festival. The bar downstairs is run by friendly and knowledgeable bartenders. Importantly, a big breakfast buffet is served in the morning.
Deets:
Checkin: 15 walk from the train station
Breakfast:Great and large breakfast buffet
Dinner: Walk
Noteworthy: Amazing balcony
Day 1 - Malveira da Serra (Coast)
Distance: 9 mi
Elev. gain: 1020 ft
Time: 6 hours
Lunch: Mar do Guincho
A beautiful morning for a beautiful hike. We grabbed a nice breakfast and hit the road at 10am. The path, which follows PR02 CSC, was paved and flat most of the trail, with many bikers and joggers (you could rent scooters to cut the distance too). We passed an interesting outdoor mall, Casa da Guia, I would recommend. Then the city ends and it's just you, the coast, and the random fancy seafood restaurants that appear every mile.
Lunch
After a few hours, you come up on a beach area with a cluster of seafood restaurants. These look like they get packed in season but we got there at 12:50 in December. I highly recommend you stop at Mar do Guincho, this place is the reason people speak so highly of Portuguese seafood. Staff was wonderful and fancy.
I got the Rock Lobster Curry and it was a pile of lobster meat. I will always remember this dish
Neas got the octopus salad (which was fantastic) and vegetable soup. The idea of just veggies made the restaurant sad so they threw some shrimps in it. Classy! To indulge further, we had port wine and Semifreddo.
After lunch was a show of watching a dog dig a deep hole in the sand aggressively.
Back on the Road.
The next leg of the trip can take you through a section of beach or you can head up the road (ER247) and making a left at “Abano”. This is also where the PR04 CSC Loop starts. Make sure to check out Forte do Guincho and this beautiful diving looking place, Restaurante Abano that was closed for the holiday and I would have killed to try out.
To reach the town, Malveira da Serra, the next section takes you through the Abano Trail and the only hill of the day. Malveira da Serra was a cute town. We didn’t see much open but it was New Year's Eve. Our hotel offered a food delivery service for most nights but we had something lined up for the holiday.
360 Tour
Bites and Stay - Dream Guincho
Now this was an experience! This stay was has a literary theme, with each room named after a book and art installations of books placed tastefully throughout the hotel. There was a sauna (we enjoyed) and a pool (which we would have enjoyed if it wasn't winter). Instead, we warmed up by the firepit.
It was New Year's, so we got to enjoy a special event with many wonderful people. The food was amazing and fun. The drinks were plentiful!
Thank you for having us!
Checkin: Follow Google Maps! The driveway is around the back on R. do Moleiro. It's gravel for 2 seconds, not bad.
Perfectly set up balconies overlooking the coast.
Dinner: A delivery service
Breakfast: Wonderful. Breads, meats, yogurt and cheeses, cooked eggs too!
Wish we had another day there. Giving it 5 Dinkies!
Day 2 - Azoia (Mountain)
Distance: 4.5 mi
Elev. gain: 1362 ft
Time: 3 hours
Lunch: N/A Short day
It took a hot second to recover from last night but a big breakfast was the perfect medicine! Lots of freshly cooked eggs, pancakes and many other bites. We thanked the wonderful hotel again and hit the road.
Today’s goal is to hike up the mountain to Sanctuary of Peninha and down to Azoia. Dream Guincho had a shortcut in their backyard to the sanctuary but today was a short day and we had some time to kill, so we decided to skip it. This route is made up of 2 PR trails (PR03 CSC and part of PR10 SNT). We head through Malveira da Serra, to pick up snacks and then headed up into the forest.
The path to the sanctuary is quite beautiful. The calm forest path that takes you around to an amazing view of the coast. You forget how high up you are! The sanctuary has a lot of fun structures to walk around and when we got to the top, we got to meet the king of the castle!
After paying respects to his royal fluffness, we left the castle, headed right on PR10, and into the confusing woods. Once inside there were MANY trails. It looked like half of them were walking paths and half were for mountain biking. I recommend taking whatever path is easiest for making it down the hill and to towards road EN247 into Azoia. This is a recommended stop for the great views and access to Cabo da Roca & Ursa Beach.
360 Tour
Bites - 3 Gomez
This place had such great food, we went here twice! The morcia was so flavorful and slightly crisp. The squid and shrimp skewer was prepared perfectly. The rule for wine in Portugal is get the house! It will always be better than any wine you had before coming to Portugal so don’t try to read the wine menu and mess it up!
Got too excited, forgot pics. Sorry
No issues with a table in off season so maybe reserve in advance
Amazing Food and Staff. Another 5 Dinkies!
Stay - Charm Nature
This was a very pretty place, built for instagram most likely. With very few guests, we mostly had it to ourselves. It was just us and a very nice woman running the empty hotel. Our room was gorgeous, with a tub by the window and a balcony to watch the ocean.
We spent some time in the common area playing our travel dice game, Qwixx, enjoying the bar and watching the sunset. We also watched a black cat living its best life, drinking from the pool, sleeping on roofs (the usual cat things).
Also, everything is made of cork!
Note: The place is a bit too pricey for the winter, I'm sure it's packed in the summer. The operators we dealt with during booking said the pool was heated and we could book massages, not really true. We also ran out of hot water a few times so be careful during cold periods.
Deets
Checkin: There is a bell to ring and they let you in. There is someone on prem to get you into your room.
Breakfast: A work of art! Tasty, fresh, and beautiful. Huge selection of coffees, juices, baked goods and a menu of impressive items.
Nearby: Town is a few minutes walk with some restaurants and cafes
Day Extra - Cabo da Roca
Distance: 4.5 mi
Elev. gain: 750 - 1000 ft
Time: 4.5 hours
Lunch: Mira Azóia
This section can easily be added onto the previous day or skipped. We did a loop to see two major sites in Portugal, Cabo da Roca and Ursa Beach. There are two options to get there:
Caminho do Peraduço (We did the way there): This road leads to a trail. The trail will have a steep section that also goes through cactus and bees. Follow our map because the other routes in the area are more dangerous.
Estrada do Cabo Roca (We did the way back): This road is tiny and packed. Be careful when walking on it. There are also buses so that may be a better option
It's the most western point of continental Europe. People love it there and the view is gorgeous. After you are done looking at ocean, head back up the road 2 feet and you'll find a great trail for the coast.
The trail takes you towards the beach. Just note that the trail is on a very tall cliff and the beach is on sea level. If you want to go down there, you gotta come back up. We did not go down there.
Lunch
We finished the loop and went down the busy road, back into town to get lunch at Mira Azóia. We were lucky to arrive right when it opened, so we got the best seats with a view of Cabo da Roca! Lunch was more fresh skewers, olives, octopus, and wine!
Stay - Penedo Escape Sea Suites
Apartments with my favorite bathroom ever! With a powerful shower and huge jacuzzi tub, it felt like a spa. The property was very pretty and had a pool (too cold for winter).
Breakfast was simple and nice. They had a little bit of everything, a plate was made with cold-cuts, breads, yogurt and more. It was served in a fancy hut overlooking the ocean.
Deets
Checkin: Self check-in with a gate. Instructions were clear.
Breakfast: Included
Dinner: We got 3 Gomez again to go! We love it there.
Nearby: One cafe but closed in the winter
Noteworthy: Shower and Bath!
Day 3 - Parque Natural de Sintra-Cascais
Distance:7 mi
Elev. gain: 1,400 ft
Time: 5.5 hours
Lunch: Refugio do Ciclista
Leaving Ulguiera
We found a nature trail that lead from Ulguiera to Almocageme. Just make sure when you make it to Almocageme to bear left because the path to the right it a dead end. Almocageme had a winery that unfortunately, wasn't open so we will have to hit it up next time.
Lunch
This was the only snack bar we had on our trip and it was everything we wanted. Quite, cute, and friendly, Refugio do Ciclista was a great last stop before heading into the national park. We had a pastel de nada and port wine before we headed into the woods.
An ancient convent deep in the park that is well known for being made up of cork. TThe Cork Convent was home to many friars back in the day who were known for their connection with nature and using cork for insulation, padding and style. Tickets can be purchased online or at the gate.
After our cork detour, we headed through the park to Lagoa dos Mosqueiros. The lake of mosquitos wasn't an issue in the winter but I would probably avoid in the warmer months. The park has many trails so pick your own path on the way to Parque e Palácio de Monserrate
360 Tour
A must do on the way to Sintra. The entrance is on the top of the hill and leads to the gardens and palace at the bottom. The palace has a unique Moorish style that reminded us of the Alhambra, with a fancy fountain in the middle. Next was the cafe, where we got a bottle of wine and sandwiches, and watched a cat clean itself for a long time.
Tickets: Would recommend buying ahead of time
360 Tour
Now, on to Sintra to finish our journey. The N375 was perfectly safe to walk down and didn't take us long to hit town. It looks like the area is trying to reduce the number of cars in town so walking is the right idea.
Stay - Villa Bela Vista
Amazing view of Sintra and a balcony!
Deets:
Checkin: The entrance is on the road, right next to cars. Buzz to get in to reception
Breakfast: A very nice breakfast with baked goods and prepared eggs.
Dinner: Went into town
Noteworthy: Amazing balcony
Sintra
A UNESCO World Heritage site that earned it by being gorgeous, full of culture, architecture, and food. Famous for the beautiful foggy mornings and that small period of time Lord Byron visited and had a good time. We planned for a 2 day stay which is the perfect amount of time.
Do NOT drive here.This town is not made for cars, and yet we see a lot of people spend hours waiting in traffic, looking for parking, and suffering (like all car people deserve).
Activities
So many castles and gardens to explore
The must do in Sintra! A huge estate with many castles, chapels, museums, Regaleira Tower and the main event, the Poço Imperfeito. We got there early and made sure to hit the Initiation Well (Poço Imperfeito) first, to avoid lines. After, we put on a podcast about Lord Byron's problematic history and strolled through the rest of the gardens.
Tickets: Purchase ahead of time! Each ticket has an entrance time. Be sure to get to yours 15 to 30 minutes before. Tour not required.
360 Tour
A more off-the-beaten-path, private palace with fewer people. We enjoy chilling here more than Quinta da Regaleira to be honest.
We got to explore Chalet Biester, which was featured in the film The Ninth Gate. There was a room in the basement where you can see props from the movie.
Tickets: We bought the day of but it was January.
Others
The Moorish Castle (Castelo dos Mouros) - We didn't go because it was too foggy but there are plenty of busses or a nice hike to get there.
National Palace of Sintra - Saw it from our balcony, no big deal.
Sips and Bites
We loved this tavern. Nestled between two winding side roads, it's perfect for a quick bite or a decadent charcuterie board. The hours were more accommodating. Most places were closed, so we went a couple of times.
Others
Dona Maria - Great view and patio.
Messias Wine bar - Great selection of port wine with flights but the pricing is a little scammy
Estrada Velha - Tavern with fat francesinha
Hambúrgueria da Ferraria - We don't do hamburgers but we do love a patio that overlooks Sintra
Maps
Notes: This was made before our trip. Here are the deets
