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Party and nightlife
Relax
Nature and adventure
City and cultures
Monuments and history
Physical effort
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Itinerary

Discover the very best of Portugal in just five days — and trust us, five days will never feel so full.

Portugal has a way of getting under your skin. Maybe it's the melancholy beauty of a Fado singer echoing through a tiled Alfama backstreet. Maybe it's biting into a warm pastel de nata with the Tagus glittering below you. Or maybe it's standing on the walls of a Moorish castle above Sintra, wondering how a place this fairytale-perfect actually exists. Whatever it is, it hits hard — and it stays with you.

Over five days, we'll ride the rattling Tram 28 through Lisbon's historic heart, lose ourselves in the palaces and mystical gardens of Sintra, trace Portugal's Age of Discovery along the waterfront in Belém, and end our days the way the Portuguese do — late, loud, and happily. Bairro Alto and Pink Street will see to that.

This is Portugal at its most iconic. Come and see what all the fuss is about.

A stylized map showing a circular travel route that starts and ends in Lisbon, with three intermediate stops indicated.
A dense neighborhood of white houses with red-tiled roofs sits on a hillside against a soft, pastel sunset sky.

Check-in: our adventure starts in Lisbon

After checking into the hotel in Lisbon city centre, we'll head to a miradouro (viewpoint) to catch the sunset and start getting to know your fellow travellers. In the evening we’ll have our welcome dinner, the perfect way to get to know Portuguese culture with a plate of Bitoque or Bacalhau à Brás. After dinner, we'll grab a drink and explore the nightlife around Bairro Alto or Pink Street.

A cityscape of colorful buildings with red-tiled roofs seen from a terrace at sunset, with the sea in the distance.

Tram 28 & Alfama

Today we’ll hop on the iconic Tram 28 to head up to the famous neighbourhood of Alfama. We’ll get a sneak peak at Lisbon Castle before we take a walk through Lisbon’s iconic narrow streets, stopping by the impressive Lisbon Cathedral, miradouros overlooking the city, all the way down to Praça do Comércio.

After lunch, we’ll walk to the top of Elevador de Santa Justa to see the breathtaking view of Lisbon from above. This is also a perfect time to try a local delicacy… Pastel de Bacalhau, filled with Serra da Estrela cheese!

Traditional Fado Dinner

After some free time to shop, relax, or stop by the hotel to change, we'll head back to the winding streets of Baixa or Alfama to experience a traditional Fado dinner, one of the most authentic and emotional parts of Portuguese culture. After that, the world is our oyster, whether you want a good night's sleep or to party until sunrise..!

A red and white building overlooks a historic town with a palace featuring two white conical chimneys, under a partly cloudy sky.

Day trip to Sintra

Today we leave Lisbon to explore the magical town of Sintra.

We’ll visit the colourful and iconic Pena Palace, one of Portugal’s most famous landmarks. After exploring the park and gardens that surround the palace, we'll take a look inside for some breathtaking views and some of the most Instagram-worthy moments of the trip. From here, we can choose to visit the Moorish Castle, Quinta da Regaleira, or shop and grab a pastel de nata in the town centre. 

Cabo da Roca

From Sintra, we'll head onwards to Cabo da Roca, the westernmost point of mainland Europe, to watch what might just be the best sunset you've ever seen. We’ll head back to Lisbon in the evening, with time to relax or grab dinner together.

An ornate stone fortress with turrets stands in the water next to the shore under a clear blue sky.

Exploring Belém

This morning we start by taking the train to Belém, one of the most historic and picturesque areas of Lisbon. Here you’ll be able to visit the stunning Jerónimos Monastery, see the Belém Tower, go to the top of the Monument of the Discoveries, and try the original pastel de nata (Pastel de Belém), in it’s birthplace! After a quick stop for lunch, we’ll jump back on the train and head out to Cascais, a place that perfectly captures the relaxed, sun-soaked lifestyle of the Portuguese Riviera.

Relaxing in Cascais

We’ll spend the afternoon enjoying everything Cascais has to offer. Here you can relax or walk down the beach, take a dip in the Atlantic Ocean, wander through the charming old town and shop for souvenirs, grab a coffee or ice cream by the marina, or head down to Boca do Inferno, where you can see the ocean crash dramatically against the cliffs.

After soaking up the sea air and catching one last sunset together, we’ll head back to Lisbon. Dinner, drinks, and one last night out await, whether that means cocktails on Pink Street or getting lost in the bars of Bairro Alto.

An outdoor restaurant with bright orange chairs is set up on a cobblestone street under a large bridge at dusk.

Check-out and goodbyes

This is the final day of our trip, and time to say goodbye (for now!). If you have time before your departing flights, we can get brunch together in the city or head to LX Factory, a historical industrial complex underneath the 25th April Bridge where you'll find an array of arty retailers and unique cafes.

What's included

What's not included

Roundtrip flight to/from destination
  • Food and beverages when not specified
  • All the extras you'll be able to fit in your backpack
  • Anything not mentioned in the "What's included" section

Optional activities

Please see below extra optional activities that you can experience during your trip. Your Group Leader will be happy to assist with organizing these activities for the group. Availability may vary depending on location and group preferences. Please note these activities are provided by third party suppliers and liability rests exclusively with these third party suppliers.

  • Lisbon Castle - approx. USD24

  • Lisbon Cathedral - approx. USD12

  • Moorish Castle - approx. USD17

  • Quinta da Regaleira - approx. USD23

  • Jerónimos Monastery - approx. USD24

  • Belém Tower - approx. USD17

  • Monument of the Discoveries - approx. USD14

Additional info

Learn more about accommodation, transport, and other useful travel information.
  • Small hotels or apartments in Lisbon city centre, with private bathrooms and breakfast included
  • Transport to and from destinations on the itinerary may include riding the bus, tram, train, and metro.
  • Info on private roomsShow all details

Why WeRoad

  • Small groups, on average 11 people

  • Move or change your trip for free up to 31 days before departure

  • Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed

The Group Leaders

Our Group Leaders are chosen because they’re people just like you: passionate travelers who share the experience authentically, while having the skills to take care of the organisation, and help you get the most out of every moment of the trip.

Find your flight

For this trip, we recommend arriving and departing from these airports.

ArrivalLisbon (LIS)
ReturnLisbon (LIS)
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WeRoadX

This is a WeRoadX

A trip designed and created entirely by an experienced WeRoad Travel Group Leader.

This is a trip designed and created entirely by an experienced WeRoad Travel Group Leader. They organise the whole trip: from defining the itinerary to selecting accommodation and on-site experiences. On the WeRoad website you can book the trip and manage it in MyWeRoad, just like any other WeRoad.

FAQs – Frequently Asked Questions

About this trip

About WeRoad

About Portugal

From$ 694
-8%
$ 636
Book with $ 0
Free trip change
Interest-free installments