“Life is either a daring adventure, or nothing at all .” - Helen Keller

Portugal & Madeira - Our 16 day Itinerary

Have you been dreaming of a European adventure and don't know where to start?

Have you ever dreamed of visiting the Eiffel Tower in Paris or the Coliseum in Rome. Are you excited at the thought of sipping an espresso in a cute little cafe on cobblestone streets in a beautiful European city? With so many stunning countries and places to choose from, selecting your favourite European destination can feel overwhelming and confusing.

It certainly was for me. I was lost in a sea of information when I started researching places to visit in Europe. Thankfully, the task of narrowing it down to a few beautiful countries was made easier because Vasco (the other half of the Gen X Travellers) was born on the Island of Madeira. He migrated to Australia when he was five years old and not having visited Europe since leaving his beloved hometown of Ponto Do Sol in 1972, we decided in 2024 that it was time to explore his roots. Hence, Portugal was at the top of our list.

And let me tell you, Madeira and Portugal did not disappoint. We loved everything this beautiful country has to offer no wonder so many people are moving to live here.

Portugal and Madeira offer a perfect blend of history, culture, stunning landscapes, and delicious cuisine. This wonderful country is known for its high quality of life, free health care, affordable cost of living, quality education, and low crime rates. With its rich culture, friendly people, fabulous food & easy access to other European cities, what's there not to love?

In this blog post, I'll share our 16-day itinerary that takes you through the highlights of these two beautiful destinations.

1. Lisbon (3 nights) Here are our top things to do in Lisbon.

• Explore the historic areas of the Chiado, Bairro Alto and the Alfama districts. Experience a traditional Fado often described as a mournful reflection on the bittersweetness of life. Listen to soulful, haunting voices accompanied by the strings of a guitar that transport you to another place and time.

• Watch a sunset from one of the many beautiful miradouros. Our favourites are Miradouro de Santa Catarina & de Santa Luzia.

• Stroll down Rua Augusta. This bustling pedestrian-only street is lined with shops and cafes, which ends at the Praca do Comercio, one of the world's most beautiful squares.

• Spend an afternoon in the Lx Factory district. An old warehouse and industrial area that has been transformed into a trendy and hip area where you will find the Ler Devagar, one of the most beautiful bookstores in the world.

• Visit the Belém Tower and Jerónimos Monastery a UNESCO World Heritage building Inspired by Vasco da Gama’s voyage to India. Later relax at a cafe and experience the best Pastel De Nata at the famous Pastéis de Belém.

• Visit Castelo de São Jorge on Lisbon’s highest hill; this historic castle offers panoramic views of this beautiful city.

• Enjoy a sunset cruise along the Tagus River.

2. Madeira (5 nights - Funchal) Best things to do in Madeira.

• Hike to Pico do Arieiro and walk the famous stairway to heaven. If you don't want to do the hike, then drive or book a bus transfer to experience a sunrise in the clouds at Pico do Arieiro. It's an unforgettable experience.

• Take a cable car ride to Monte Palace, visit the Igreja de Nossa Senhora do Monte (church) and then take the toboggan ride, which stops at the halfway point down back to Funchal. You can then either catch a bus or taxi or walk by foot back down to Funchal.

• Catch a bus or take a different cable car ride from Funchal to the Madeira Botanical Gardens, which has more than 2000 exotic plants from all over the world. You'll also have spectacular views of Funchal.

• Visit Porto Moniz, home to the largest volcanic natural pools in Madeira. While you're in this area, visit Seixal Beach, Miradouro do Veu da Noiva, which has a nice viewpoint of the waterfall falling into the Atlantic Ocean and visit the picturesque town of Sao Vincente.

• Visit Cabo Girão Skywalk, Europe's highest sea cliff (589m) and walk the glass deck set on the cliffside suspended in air, taking in the breathtaking views over the Atlantic.

• Explore the old town in Funchal & don't miss the CR7 Museum if you're a big soccer fan.

3. Porto (3 nights) Best things to do in Porto.

• Visit the iconic Ribeira district, walk the medieval alleys down to the Douro River, explore the promenade lined with colourful 18th-century townhouses and indulge in the restaurants, bars, craft markets and street entertainment. Ribeira is one of Porto's most picturesque, authentic and liveliest promenades.

• Walk around this beautiful city and explore its charm and beauty. Walk across the Dom Luís I Bridge; once on this side known as Gaia, walk the riverfront promenade, stroll through the World Of Wine (WOW) district and finish your day with a wine tour and tasting at one of the many Wine Cellars. We tried the Ferriera Porto Winery and loved it.

• Enjoy a sunset with port wine and cheese at one of the many miradouros (viewpoints). Try the Jardim do Morro near the Mosteiro da Serra do Pilar, an old monastery near the Dom Luís I Bridge, or if you have extra time, visit the Jardim do Passeio das Virtudes, which has terraced gardens and a sweeping view of the river.

• Explore the historic centre and visit Clérigos Tower, the São Bento Train Station, Porto Cathedral, also called Sé do Porto, the Capela das Almas (Chapel of the Souls), Livraria Lello Bookstore, walk down Rua de Santa Catarina for shopping and visit Bolhão Market for traditional Portuguese food for your picnic.

• If you have an extra day, book a boat cruise to the Douro Valley.

4. Coimbra (1 night) or spend an extra night in Nazare or Porto.

Coimbra, is a captivating city nestled in central Portugal, is renowned for its rich history, stunning architecture, and vibrant student life. As one of Portugal's oldest cities, Coimbra boasts a fascinating past, evident in its historical centre, dominated by the University of Coimbra.

• The main thing to do in Coimbra is to visit the ancient university, with its iconic library and stunning cloisters, which is a UNESCO World Heritage Site.

5. Nazaré (2 nights) Best things to do in Nazare.

Nazaré is a picturesque fishing village renowned for its dramatic coastline and world-class surfing waves. The Praia do Norte beach, in particular, is famous for its massive waves (October - March), attracting surfers from around the globe. Nevertheless, even though we didn't get to see the big waves (we'll save that for another trip), this town is gorgeous. Nazaré offers a charming historic centre, stunning coastal views, and delicious seafood.

• Relax on the beach, walk the beach promenade and enjoy a golden sunset.

• Visit the Sitio viewpoint for panoramic ocean views. Visit the the Lighthouse Museum. This town is made for relaxing and mingling with the locals.

6. Sintra (1 night or stay in Lisbon and take the train for the day)

Sintra, a captivating town nestled in the hills near Lisbon, is often referred to as a "fairytale town." You'll need an entire day as there are so many places to see, and walking around this area is breathtaking. We visited Pena Place and Quinta da Regaleira.

• Explore the Pena Palace and Park.

• Walk from the town centre to Quinta da Regaleira.

• Walk around the historic centre.

7. Lisbon (1 night)

Relax and enjoy the city one last time. Instead of booking accommodation in the old town neighbourhoods like Alfama and Bairro Alto, stay near the Lisboa Oriente Train Station. This is the main train station in Lisbon, located in the Parque das Nações neighbourhood, which gives you access to all major routes and is also close to the airport. This area has a lot to offer, from shopping malls, walking promenades and the Lisbon Oceanarium. You'll experience another side of Lisbon.

As you can see, there is so much to explore in Portugal.

This sixteen-day itinerary was part of an eight-week trip to Europe, during which we visited Spain and Italy after leaving Portugal. If you have more time you can extend your stay in Portugal by visiting the Algarve like we did. At the end of this itinerary, we took a bus down to the Algarve and then travelled to Seville before heading off to Italy.

As first time travellers to Europe, we wanted to avoid the hassles of driving. We found that Portugal's public transport system was very accessible. Throughout our trip, we mainly used FlixBus, along with regional and local trains. On occasion, we relied on Bolt, as it is often inexpensive and sometimes quicker than taking the train or bus.

Additional Tips:

1. Consider extending your trip to the Algarve. It offers beautiful beaches, stunning cliffs, and charming towns like Lagos and Carvoeiro.

2. Book accommodations in advance: Especially during peak season, it's recommended to book your accommodation in advance, particularly in popular destinations like Lisbon and Porto.

3. Embrace the local culture: Try the local cuisine, learn a few Portuguese phrases, and immerse yourself in the local way of life.

4. Pack comfortable shoes: You'll be walking a lot, so make sure you have comfortable shoes.

5. Stay hydrated: The Portuguese sun can be strong, so drink plenty of water.

I hope you found this blog post helpful. If you would like any other info, feel free to send me a message through our socials.

Happy travels,

Anna & Vasco xx

PS: Need some help planning your next big travel adventure? Check out our FREE Ultimate Europe Travel Planner for more tips and resources.