1.Sintra – This fairytale town is full of castles, whimsical palaces and villas dotted amongst the hills of the Sintra Mountains. Only an hour train ride from Lisbon, Sintra is a resort town that was frequented by Portuguese nobility who flocked to the mountains to escape the summer temperatures in Lisbon. It makes the perfect day trip from Lisbon; however, spending a few days in this peaceful town will be a time you won’t regret.

We spent two nights in Sintra to fully experience all that this town has to offer and although the weather didn’t cooperate while we were there, Sintra was probably our favourite stop on our Portugal trip.

What to Do:

• Quinta da Regaleira
• Pena Palace (Palacio de Pena)
• Moors Castle (Castelo dos Mouros)
• Monserrate Palace
• Palácio Nacional de Sintra

How to Get There:

• About 1 hour on the Linha de Sintra from Lisbon’s Rossio Station to Sintra Station
• Once you arrive in Sintra, Bus 434 is a one-way loop starting at Sintra Station that stops at some of the major tourist stops including the National Palace, Moors Castle and Pena Palace.

Where to Eat:

• Cafe Saudade – breakfast, coffee, tea and sandwiches
• Romaria de Baco – one of the best meals we had in Portugal
• Tascantiga – small plates and friendly service
• Piriquita – bakery to try the local specialty, the Travesseiro, an almond pastry

Where to Stay:

• Chalet Saudade

2. Cascais – This seaside resort town makes an easy day trip from Lisbon. Similar to Sintra, Cascais is a charming town 45 minutes from Lisbon which was chosen as a royal retreat by King Luis I of Portugal. Other aristocratic families also flocked to Cascais where they built their summer residences. Today you will still find the elegant manors overlooking picturesque beaches. One such beach, Praia da Rainha or the Queen’s beach, was so named because it had been chosen as the queen’s private beach.

We walked from the Cascais train station along the coast past Praia da Rainha beach to Boco do Inferno. There we learned of the astrologer and mystic, Alistair Crowley, who faked his own death at these cliffs in the 1930s as part of a publicity stunt. After a wonderful lunch back in the town of Cascais at 5 Sentidos, we walked along the seawall in the opposite direction towards the neighbouring town of Estoril. The sea wall took us past several more beaches, the Alberto Romano Oceanic Pools and some elegant seaside residences. We hopped back on the train at the Estoril train station in time for a delicious dinner in Lisbon. If the weather was warmer, we would consider renting bikes to explore the coast further to Guincho beach but we will have to save that for our next trip to Cascais.

What to Do:

• Boco do Inferno
• Praia da Rainha beach
• Cascais-Estoril promenade – 3km seaside walk between Cascais and Estoril
• Bike path to Guincho Beach

How to Get There:

• 45 min on the Linha de Cascais line from Lisboa – Cais do Sodre Station to Cascais

Where to Eat:

• 5 Sentidos – a great meal that’s worth the price

3. Nazaré – We ventured to this idyllic beach town in late October hoping to see the massive waves which are surfed by the best in the world. The huge waves formed by the underwater Nazaré Canyon are best viewed from Nazaré Lighthouse overlooking North Beach. The lighthouse also houses a small museum featuring the professional surfers who risk their lives in search of these record breaking waves.

We did see a few surfers that day but unfortunately no record breaking waves. Our adventures in Nazaré were still worth the trip due to the incredible views from the clifftop town of Sitio which overlooks the long sandy beach and charming town of Nazaré. From the viewpoint in Sitio we also learned of the legend of a 12th century knight whose life was saved by Our Lady of Nazaré. After getting lost in the fog at the top of the cliff while hunting a deer, the knight prayed to the Virgin Mary. The knight’s horse stopped in its tracks mere inches from falling off a 100 metre cliff. A small chapel, Ermida da Memoria, marks the location of this miracle.

What to Do:

• Nazaré Lighthouse – small museum on the cliffs overlooking the North Beach
• Miradouro do Suberco – views of Nazaré and Nazaré beach
• Sanctuary of Our Lady of Nazaré
• Ermida da Memoria – small tile covered chapel
• Ascensor de Nazaré Playa

How to Get There:

• 2 hour Rede-Expressos bus from Sete Rios terminal in Lisbon
• 1.5 hour drive from Lisbon
• Organized tour which combines Nazaré with Obidos and Fatima

Where to Eat:

• Aleluia Restaurant Esplanada – seafood restaurant across from Nazaré beach

4. Obidos – Medieval walled town that makes an excellent day trip from Lisbon. We enjoyed our time in Obidos simply exploring the cobblestoned streets and picturesque alleys. We climbed to the top of the walls surrounding the town for a wonderful view of the rolling hillside but wouldn’t recommend walking the length of the city walls to anyone with a fear of heights. We visited Obidos in October which made for a quieter experience without the summer crowds. Obidos also hosts a medieval fair in the summer and it is possible to stay in the castle which has been converted to a hotel.

What to Do:

• Obidos Castle
• Try the local drink, Ginja, served in a chocolate cup
• Santa Maria Church – 12th century church
• 1 hour walk around the city walls (warning: no safety railings)

How to Get There:

• 1 hour Rapida Verde bus from Lisbon’s Campo Grande metro station
• 1 hour drive from Lisbon
• Organized tour which combines Nazaré with Obidos and Fatima

Other Day Trips to Consider from Lisbon:

We didn’t have enough time to visit these other towns during our October 2018 trip to Portugal but they are on our bucket list for our next trip.

• Evora – 1.5 hour drive from Lisbon to a town famous for the skeleton adorned Chapel of Bones
• Setúbal – an area frequented by Portuguese tourists that includes the Arrábida Nature Park and the beach resort town of Comporta
• Batalha – famous for its monastery and can be paired with a trip to Fatima, Nazaré or Obidos
• The Berlengas Islands – nature reserve off the coast of Portugal which can be reached from the fishing town of Peniche