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This is a WeRoad Collection

A trip designed for ultimate comfort, with specially selected hotels and unique experiences.

Is this trip for me?

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

Porto and Lisbon, two cities staring each other down from opposite ends of the country, connected by a first-class train ride. Portugal is all about azulejos, hills, wine, and that cheerful melancholy that even has its own name: saudade. In eight days, we’re keeping it simple with just two bases, staying in 4-star hotels right in the heart of the action. We’re here to actually experience these cities, not just breeze through them.

We’ll kick things off in Porto, which cascades down to the river in tiers: the Ribeira, the Clérigos Tower, the Lello bookstore, and the cellars of Vila Nova de Gaia, where Port wine ages in barrels the size of rooms. A full day is dedicated to the Douro Valley, a UNESCO World Heritage site: we’ll visit a historic quinta, have lunch in the vineyards, and cruise the river winding through the terraces. Then, the train whisks us away to Lisbon, where our first evening features dinner accompanied by live Fado in Alfama. We’ll hop on Tram 28, head to Belém for the Jerónimos Monastery and some freshly baked pastéis de nata, and dedicate a day to Sintra, exploring the Palácio da Pena and Cabo da Roca, the westernmost point in Europe. Our final day is all about the local side of Lisbon: the LX Factory, Time Out Market, and a night out in Bairro Alto.

First francesinha

We arrive in Porto and the first thing you notice? It’s all downhill. The city tumbles right down to the Douro, with its iconic azulejos facades and laundry drying in the windows. Hotel check-in done—three nights, no packing and unpacking required—and then it's time for our first stroll to the Ribeira, the UNESCO-listed riverfront, with the Dom Luís I bridge looming above us. For dinner, there’s only one mission on night one: the francesinha. A sandwich packed with three types of meat, buried under melted cheese and beer sauce. It’s not exactly light. It’s perfect.

Twenty thousand azulejos

Porto is best explored on foot, and today we’re doing it with a guide who knows exactly where to look. We’ll climb the Clérigos Tower for a 360-degree view, step into Livraria Lello with that red staircase that seems practically made to be photographed, and swing by São Bento station, where twenty thousand blue tiles tell the story of Portugal right on the walls of a train station lobby. In the afternoon, we’ll walk across the bridge and head down to Vila Nova de Gaia for a visit to a historic Porto wine cellar and a tasting of three wines. Tawny, ruby, vintage—you’ll really taste the difference.

Terraced vineyards

Day trip to the Douro Valley, just an hour and a half inland. It’s the world’s oldest demarcated wine region, and you can tell: the terraces cascade down to the river like giant, hand-carved steps in the schist, shifting colors with the seasons. We’ll visit a historic quinta, enjoy lunch among the vines with a river view, and spend the afternoon on a one-hour boat cruise—that’s where you’ll really appreciate just how steep those hills are. This is our WOW experience, and by the end of the day, you’ll see exactly why it took centuries to build.

Changing cities

A relaxed breakfast, then off to the station: we’re taking a first-class train to Lisbon—three hours of pure comfort while Portugal rolls by outside the window. We’ll arrive in the early afternoon to settle into our spot in Chiado, where we’ll be staying for four nights right in the heart of the city. Time for our first stroll up and down the seven hills (let’s be real, flat streets don’t exist in Lisbon!) and then, in the evening, we’re heading to Alfama, the oldest district, for dinner accompanied by live Fado. Two guitars, one voice, and a word that defies translation: saudade. Stop talking, just listen.

Classic Lisbon

Let's kick things off with the iconic yellow Tram 28. It climbs through the narrow alleys, brushing against the walls—this isn't just for tourists, it's how the locals actually get to work. Next up, Belém, the district of discoveries: we'll see the Jerónimos Monastery with its stunning Manueline cloister and the tower standing right in the middle of the Tagus. Right next door, you'll find the bakery that's been serving up pastéis de nata since 1837, using the original monks' recipe. They come out of the oven piping hot—sprinkle some cinnamon on top, and trust us, you won't be able to stop at just one. Free afternoon.

The westernmost point of Europe

Just forty minutes from Lisbon lies a place that looks like it stepped straight out of a picture book. Sintra is a hill wrapped in mist and filled with absurd palaces, the most absurd of which is the Palácio da Pena: yellow, red, and blue, complete with turrets and battlements placed there by a romantic king who wanted a fairytale castle and simply built it. In the afternoon, we head down to Cabo da Roca, the cliff where Europe ends: there's a monument with a quote from Camões — "where the land ends and the sea begins" — and a one-hundred-and-forty-meter drop right beneath your feet.

Lisbon, take it easy

The last full day is when we finally stop chasing monuments. We’ll start the morning at LX Factory, an old textile factory under the 25 de Abril bridge that’s been transformed into a hub of bookstores, design studios, and cafes. For lunch, it’s Time Out Market: a covered market where the city’s best chefs each have their own stall—thirty kitchens, one long table, and the impossible task of choosing what to eat. The afternoon is free, and in the evening, we’ll head up to Bairro Alto for our final group dinner, in a neighborhood where the streets are already buzzing with people by 9 PM.

Heading back from Lisbon

One last breakfast and one last miradouro before we head to the airport—because in Lisbon, the only way to say goodbye is from a viewpoint. Eight days, two cities, a valley full of vineyards, and a number of pastéis we’re better off not counting. Até já—which doesn't mean goodbye, it means see you soon.

What's included

  • 7 nights in 4-star hotels in Porto and Lisbon

  • All breakfasts

  • Welcome dinner on day 1, dinner with live Fado on day 4, and a group dinner on day 7

  • First-class train from Porto to Lisbon on day 4

  • Porto guided tour, including entry to the Clérigos Tower on Day 2

  • Medical and baggage insurance - (coverage limits by destination country/region - €10,000 Italy, €20,000 Europe, €30,000 World, €50,000 USA/Canada)

What's not included

Round-trip flights to and from the destination
  • Airport transfers
  • Food and beverages when not specified
  • All that is not mentioned in "what's included"

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.

  • N/A

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Additional info

Learn more about accommodation, transport, and other useful travel information.
  • Transport
    First-class train between Porto and Lisbon, private van for your out-of-town excursions, and public transport to zip around the city.
  • Documents

    You'll just need a valid ID card for travel or a passport. No visa required, since Portugal is in the European Union.

  • Physical rating

    Low. You'll be doing quite a bit of walking, and since both Porto and Lisbon are built on hills, you'll just need a pair of comfy shoes. That's it!

  • Meeting point and goodbyes

    We'll meet up on Day 1 at Francisco Sá Carneiro Airport in Porto. The adventure wraps up on Day 8 in Lisbon.

  • 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.

ArrivalPorto (OPO)
ReturnLisbon (LIS)
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FAQs – Frequently Asked Questions

About this trip

About WeRoad

About Portugal

From$ 1,970
-15%
$ 1,669
Book with $ 0
Free trip change
Interest-free installments