Amazing Five Days in Lisbon, Sintra and Cascais!

Are you heading to Portugal? This 5-day Lisbon itinerary lets you discover the best of the city along with magical day trips to Sintra and Cascais. From historic sights to breathtaking landscapes, prepare for an adventure filled with culture, charm, and unforgettable moments!

Day 1: Arrival & Alfama Exploration

Welcome to Lisbon! After you settle into your accommodation, ideally in the heart of Alfama or Bairro Alto, kick off your journey. Start by wandering through Alfama, the city’s oldest district. You’ll find a maze of cobblestone streets, colorful houses, and a lively atmosphere.

Lisbon Cathedral (Sé de Lisboa)

Begin with a visit to this famous cathedral. This Gothic masterpiece remains a must-see, and even better, entrance is free.

Miradouro de Santa Luzia:

Just a short walk away, this scenic viewpoint offers breathtaking views over Lisbon and the Tagus River. The terrace is adorned with beautiful azulejos (traditional Portuguese tiles) and provides a perfect spot for photos. That’s why this is my favorite viewpoint in Lisbon. Snap some photos or simply soak in the peaceful surroundings. Pro Tip: watch the sunset from here!

Tram 28 Ride

If you want to experience the heart of Lisbon like a local, hop on the iconic Tram 28. This vintage tram takes you through some of the city’s most charming and historic areas, including Alfama, Graça, Baixa, and Estrela. It’s not just transportation; it’s an adventure through narrow streets, steep hills, and past famous landmarks like the Lisbon Cathedral and the Miradouro da Graça.

This line starts at Martim Moniz Square, and while the line at this first station can be long, it’s your best chance to secure a seat. If you board at later stops, like the second one at Martyrs of the Republic Square (Largo do Martim Moniz), it might be harder to find a seat, especially during peak hours. So, if sitting is a priority, it’s worth the wait at Martim Moniz. A ticket costs €3 per ride if you don’t have a city transportation pass. If you have a pass, the ride is free, making it a budget-friendly way to explore Lisbon.

As the evening approaches, treat yourself to a hearty Portuguese meal in a nearby tavern. Alfama boasts authentic eateries that offer traditional dishes like bacalhau and grilled sardines. After dinner, if you’re up for it, explore the nightlife in Bairro Alto, where bars and music fill the streets.

Day 2: Discovering Belém’s Historic Gems

After a good night’s rest, head west to Belém, a district rich in history and culture. Known for its maritime heritage, Belém hosts some of Lisbon’s most iconic monuments.

Jerónimos Monastery

Begin at this UNESCO World Heritage site, an architectural masterpiece that symbolizes Portugal’s Age of Discovery. The monastery’s intricate Manueline architecture reflects the wealth and power of the Portuguese empire. Explore the stunning cloisters and the impressive church, where famous figures like Vasco da Gama are buried. Admission costs €12.

Belém Tower

Afterward, walk along the river to Belém Tower, another symbol of Portugal’s maritime past. The tower’s unique design showcases a blend of Gothic and Moorish influences. You can climb to the top for spectacular views of the river and city, admission costs €8. However, judging by its location, I don’t think the top view is much different from observing it from the outside.

MAAT (Museum of Art, Architecture, and Technology)

Then, stroll to this modern museum along the waterfront. Here you can explore contemporary art and innovation, admission costs €9.

Pastel de Belém

No trip to Belém is complete without trying the famous pastel de nata. Head to Pastéis de Belém, the original bakery that has been perfecting this creamy custard tart since 1837. Enjoy it warm, sprinkled with cinnamon and powdered sugar, for just €1.20. I tasted many pastéis de nata in Lisbon and I have to admit that this is my favorite one!

Day 3: Sintra – A Fairy Tale Escape

Get ready for a day filled with magic! Today, we’re off to Sintra, a UNESCO World Heritage site known for its stunning palaces and lush landscapes.

Take a scenic train ride from Rossio Station in Lisbon to Sintra, which takes about 40 minutes. You can buy a combined train and bus ticket for around €14.5. This covers the round-trip train fare and access to Bus 434 & 435, which takes you to the key attractions in Sintra.

Below is a map to help you navigate Sintra’s stunning palaces. With seven palaces to explore, it can feel overwhelming to visit them all in a single day. If you’re short on time, I recommend focusing on 2-3 palaces to fully enjoy each one without feeling rushed. This way, you can take in the beauty and history at a relaxed pace, making the most of your trip to Sintra.

Pena Palace

Your first stop is this whimsical castle that looks like it’s straight out of a storybook. Completed in the 19th century, the palace blends architectural styles like Neo-Gothic, Neo-Manueline, and Moorish influences. Inside, explore vibrant rooms filled with history. Outside, wander the lush gardens featuring exotic plants and stunning views of the surrounding hills. To save time, you can buy tickets online through the official Parques de Sintra website or platforms like GetYourGuide. The cost for the combined palace and park entry is €20. Booking online also helps you skip the ticket queue and secure your spot during busy periods.

Moorish Castle

After Pena Palace, head to the Moorish Castle, an ancient fortress dating back to the 8th century. Perched on a hilltop, this castle offers panoramic views of Sintra, Lisbon, and the Atlantic coast. You can walk along its rugged stone walls and explore the medieval ruins. Tickets can be purchased online via the Parques de Sintra website or through platforms like GetYourGuide for €10, which allows you to skip the lines and plan your day more efficiently.

Quinta da Regaleira

Next, visit the Quinta da Regaleira, a palace and estate filled with mystical symbolism and enchanting gardens. Its underground tunnels, secret passageways, and the famous Initiation Well make it a unique experience. The palace’s architectural style draws on Gothic, Renaissance, and Manueline influences. Tickets are available online through the official Quinta da Regaleira website for €12 or booking platforms like GetYourGuide with audioguide for €21. Buying tickets in advance can save time and guarantee entry during busy periods.

Dinner in Sintra

After a day of exploration, treat yourself to dinner at a local restaurant. Make sure to try the travesseiros, a sweet pastry that’s a must-have. This flaky puff pastry filled with almond cream will satisfy your sweet tooth!

Return to Lisbon

Head back to Lisbon and relax after your fairy tale adventure. Consider taking an evening stroll along the waterfront to unwind.

Day 4: Cascais – Coastal Bliss

Today, it’s all about sun, sea, and relaxation as we venture to Cascais, a charming coastal town known for its beautiful beaches and vibrant atmosphere.

Catch a train from Cais do Sodré Station—the ride is a breeze at about 30 minutes. The train ride along the coast offers stunning ocean views. A return ticket costs €4.80.

Cascais Marina

Start your day at the marina, where the vibrant atmosphere and beautiful boats set the scene for a perfect day by the sea. This area is great for people-watching and taking in the fresh ocean breeze.

Santa Marta Lighthouse

Located along the stunning coastline of Cascais, the Santa Marta Lighthouse is a striking blue-and-white structure that has guided sailors since the 19th century. This lighthouse not only serves as a scenic landmark but also houses a small museum where you can learn about the history and importance of maritime navigation in Portugal. The museum features exhibits on the development of lighthouses, as well as insights into local maritime traditions. Climb up the observation deck for panoramic views of the rugged coastline, and enjoy the peaceful surroundings.

Boca do Inferno

Visit this dramatic cliff, known as the “Mouth of Hell.” The views of the Atlantic crashing against the rocks are spectacular. It’s a fantastic spot for photos, especially at sunset when the colors illuminate the sky.

Beaches

Spend some time soaking up the sun at Praia da Rainha or Praia do Guincho. Whether you want to relax on the sand or take a dip in the ocean, these beaches offer the perfect getaway

Lunch by the Sea

Savor fresh seafood at a beachside restaurant. Order the grilled sardines for a taste of local flavor. Pair your meal with a refreshing vinho verde or a glass of local white wine.

Return to Lisbon

After a day in the sun, head back to Lisbon for the evening. Consider visiting a rooftop bar for stunning views of the city skyline as the sun sets.

Day 5: Final Adventures in Lisbon

Bairro Alto and Chiado

Explore these lively neighborhoods, filled with shops and cafés. Visit the famous A Brasileira café, where you can sip a coffee and admire the statue of poet Fernando Pessoa.

Santa Justa Lift

Built in the early 20th century, it offers stunning panoramic views of the city. For a €5 ticket, you can ride the lift and take in the sights from the top. However, if you’re looking to save some money, you can climb the stairs at the back of the lift for free and enjoy the same views without the cost. It’s a great alternative for those wanting the experience without the fee.

After enjoying the views from the Santa Justa Lift, take a short stroll to Fábrica da Nata to indulge in Lisbon’s iconic pastel de nata. Known for serving one of the best custard tarts in the city, this spot offers freshly baked, warm pastries, perfect with a dusting of cinnamon and a shot of strong Portuguese espresso.

LX Factory

If you have time, visit this trendy spot filled with shops, street art, and great places to eat. Explore local boutiques, art galleries, and bookshops. It’s perfect for finding unique gifts and enjoying the local scene.

Farewell Dinner

As your Lisbon adventure comes to an end, consider enjoying a farewell dinner at Faz Frio. This charming restaurant offers a delightful menu featuring a mix of traditional and modern Portuguese dishes. The inviting atmosphere and attentive service make it an excellent choice for reflecting on your unforgettable journey. Indulge in fresh seafood or local specialties while soaking in the warm ambiance of the restaurant, making your last evening in Lisbon truly memorable.

Price list (Updated: October 2024)

  • Lisbon Cathedral: Free
  • Jerónimos Monastery: €12
  • Belém Tower: €8
  • MAAT: €9
  • Santa Justa Lift: €5
  • Pena Palace: €20
  • Moorish Castle: €10
  • Quinta da Regaleira: €12
  • Tram 28 Ride: €3
  • Train to Sintra (round-trip): €14.50
  • Train to Cascais (round-trip): €4.80