Arriving at Lisbon Airport after a 2.5 hour flight from London’s Stansted, we picked up our car hire and were off to the lovely mountains of Sintra (full guide here). Upon arriving at our hotel, the Tivoli Sintra, and admiring the mountain views, we took a tour around town. We noticed that the weather in Sintra is quite cool in comparison to Lisbon, and were worried that I hadn’t packed clothes that were warm enough for our 5 nights.
The Tivoli Hotel is conveniently located in the town centre of Sintra and adjacent to the National Palace of Sintra. From our valley view room, we had scenic, breathtaking views of the mountains of Sintra. From the Praça da República you are able to see the Palace of Pena. I chose this hotel as it was convenient to nearly everything in Sintra, although a ten-minute walk may seem easy, bear in mind you may have to go up and down a hill or two. The hotel included breakfast and the staff were quite welcoming and we were able to safely park our car in the hotel’s basement parking lot (parking is limited).
The centre of Sintra is very quiet in the evening as the tour buses and day trippers have all left back to their hotels after visiting the monuments of Sintra during the day. After a busy day of travel, we didn’t have much energy to wander around much of the area and chose a quiet dinner at Cafe Suntria.
We took an uber to Pena Palace and picked up our tickets at the ticket office. I’m grateful for the Sintra tourism board for organizing these tickets for Sonny and I. Pena Palace is extremely busy and I recommend buying your tickets in advance or you will be stuck waiting in a queue for an hour just to purchase one. I also didn’t find taking the bus up to the palace from the entrance necessary, and we hiked all the way to the top which was about ten mins. Make sure you use the toilets before heading up there.
From Pena Palace, we walked down to the Castle of the Moors which was a bit of a relief from the jam-packed Pena Palace.
It was a busy day of monuments and after walking down from the mountain we toured around Sintra National Palace.
As it was Sonny’s birthday, we headed back to the hotel to pick up our car and head to lunch at Nortada along Praia Grande.
Sonny’s birthday activities continued with a busy day of sightseeing at: Cabo da Roca and Praia Grande do Guincho. We had one of our best meals at Incomum.
We visited Monserrate Palace and Park. The grounds were very well signposted, and it was so easy to get around. The gardens and features were beautiful. After this, we drove to Cascais via Praia Grande Do Guincho, Duna da Cresmina, and Boca do Inferno. These are beautiful beaches and stunning coastal lookout points.
Caiscas is is arguably the center of the Portuguese Riviera, with its gorgeous beach in the center of town, the many boats in the water and marina, the numerous food trucks exuding delightful scents and music. We had lunch at Confraria Sushi and walked around the Cascais Marina and shopping area. It was stunning, and we couldn’t get over its beauty. After Cascais, we headed to Estoril and Praia de Tamariz, which was recommended by a local.
One of my favourite days was spent in Lisbon as it reminded me so much of San Francisco. They even have a bridge that looks exactly like ours! With the hills, ocean views and old trams, Lisbon just may be where I go when I feel homesick. We took a midday train from Portela de Sintra. We purchased our train ticket and a 24-hour transport pass within Lisbon (€10pp). Arriving at Lisbon’s Rossio we took the Azul line to Baixa and walked to Madame Petisca for the views.
Lisbon is built on several hills so there are many lookout points. Some people have said to avoid the 28E tram but we actually took it twice, some stops are more packed than others. Another line that supplements it is the 12 E.
Lisbon is full of cool neighborhoods to explore and we really liked Alfama, Principe Real and of course Bairro Alto (which was also recommended by a local).
A dinner at Cantinho Lusitano cannot be missed! It’s a little hole in the wall with no more than 5 tables. When you turn onto the street you’ll never think that there’s a restaurant on the street. Make sure you get a reservation!
Related: My Day Travel Guide to Lisbon
Day 5 began at Quinta Da Regaleira. The gardens, stone structures and caves were magnificent, although the grounds were not signposted as well as other monuments we visited earlier in the week. The cafe was in a lovely spot at the by the entrance at the base of the grounds, with plenty of options and quick service. Adding to the experience, at the entrance of the main house on the grounds, an excellent band played some pop classics.
After leaving Quinta Da Regaleria, we stopped by some quaint souvenir shops in Sintra. Our next stop was Azenhas do Mar. This place is simply a must see, and left us breathless. The beach at the bottom of the valley is surrounded by white, picturesque homes. The beach bar, with pools, was a real highlight of our trip. We took our time, watching the world go by with some bar food and drinks, listening to mellow Portuguese house played by the bar DJ.
Our evening finished with dinner at Nau Palatina. Before ordering, the manager spent time to carefully describe each item on the menu, and gave a vivid description of each dish’s flavour, texture and suggested accompanying drinks.
The slow-cooked ribs, cheese board and Moscato wines were incredible, and a fitting way to end our final night.
Praia da Adraga Beach (30 min drive)
Cabo da Roca (35 mins drive)
Rua das Padarias 1/18, 2710-603 Sintra
(+351) 219 230 626
Visc. Monserrate 44, 2710-591 Sino tra, Portugal
Things to Do:
Pena Palace and Park
Castle of the Moors
Sintra National Palace
Fabrica das Verdadeira for quejada pastries
Volta Duche 12
Food to Try: travesseiros, quejada, pasteis de nata,
Avenida Alfredo Coelho 8 – Praia Grande
Things to Do:
Monserrate Palace and Park
Things to Do:
Praia Grande Do Guincho
Duna da Cresmina
Boca do Inferno
Marina de Cascais
Mercado da Vila
Pateo do Petisco
Santini (ice cream)
Praia de Tamariz
Cozinha Do Mar
Av. São Pedro 9, 2765-278 Estoril, Portugal
Address: Av. de Nice 54, 2765-192 Estoril, Portugal
Rua de Santa Catarina 17 3º, 1200-128 Lisboa
Manteigaria (Pastries/custard pie factory)
Miradouro de Sao Pedro – R. de São Pedro de Alcântara, 1200-470 Lisboa
Principe Real Area
Pasteis de Belem
Portas do Sol – Miradouro Portas do Sol, Largo das Portas (Bairro Alto.)
Explore Alfama/ Trame 28 E
Drinks: Park Bar – Calçada do Combro, 58, Bairro Alto
Dinner: Cantinho Lusitano
Nannarella (best ice cream)
Quinta De Regaleira
Drive to Azenhas Do Mar
Av. Dr. Miguel Bombarda nº6, 2710-590 Sintra, Portugal
Calçada São Pedro 18, 2710-501 Sintra, Portugal