Discovering Portugal: A 2 Week Journey through Lisbon, Porto, Madeira and Lagos

Check into your hotel and explore your neighborhood. I recommend staying in the Baixa, Bairro Alto, or Chiado neighborhoods, all centrally located with excellent transportation options. Avenida da Liberdade is another popular area, featuring many shops, restaurants, and high-end hotels.

If you’re hungry, visit Time Out Market in Cais do Sodré, an upbeat food hall that hosts some of Portugal's renowned chefs and top-notch restaurants. A short walk away, head to the most photographed street in Lisbon: Rua da Bica de Duarte Belo. Here, you can ride the iconic Elevador de Bica, one of Lisbon’s historical funiculars. At sunset, visit a miradouro - these are viewpoints scattered across the city offering breathtaking views. I recommend Miradouro de Santa Catarina, a lovely spot where everyone gathers at sunset to enjoy some drinks and live music.

Start your day early for a full day of sightseeing! Beat the crowds by heading to São Jorge Castle before 10 a.m.; consider getting tickets in advance to skip the line. The castle, located on the highest hill in Lisbon, offers both rich history and panoramic views of the city.

Walk to Praça do Comércio, a grand plaza right on the waterfront, with the enormous Rua Augusta Arch offering stunning views for a fee.

Enjoy lunch at O Trevo, famously visited by Anthony Bourdain, and order the bifana sandwich.

Take a stroll down Rua Augusta, Lisbon's main shopping street. Nearby is the Santa Justa Elevator, providing a panoramic viewpoint at the top. Explore Convento do Carmo next door to see the ruins of a Catholic convent devastated during the 1755 earthquake.

Continue to Rossio Square, the heart of downtown Lisbon, featuring beautiful fountains and architecture. It's a great place to take a break or simply hang out.

Take a day trip to the lovely town of Sintra. Sintra is full of charming houses, palaces, and chalets, each unique and exotic. Since attractions are spread out, consider taking a tour to maximize your visit.

Start the day with Pena Palace, Sintra’s star attraction. This is a spectacular 19th-century fairytale castle showcasing Portuguese romanticism, captivating visitors with its colorful and whimsical mix of various architectural influences.

Next, visit Quinta da Regaleira, a place full of symbology and mysticism, featuring caves and the iconic initiatory well – a must-see in Sintra!

Though I missed Monserrate Palace, it looked incredible with its diversified garden and fabulous Oriental-style palace from the 19th century, and is definitely worth a visit if you have time!

For lunch, I recommend Restaurante Nortada, a Michelin-starred seafood restaurant with ocean views right on the beach.

Continue your journey to Cascais, enjoying the scenic drive along the Sintra coast with breathtaking views at Cabo da Roca. Once in Cascais, take some free time to explore the town before heading back to Lisbon.

Take the train to Porto (reserve tickets in advance to sit together).

Arrive at the stunning São Bento Station, considered one of the most beautiful train stations in Europe.

For lunch, head to Cafe Santiago to try the Francesinha, Porto's famous sandwich that consists of layers of sausage, steak, and different types of ham.

Next, walk off your calories by climbing the 75-meter Torre dos Clérigos for the best lookout view of the city.

In the evening, end your day in the Ribeira district. This is Porto’s most lively area, a perfect place for people watching, enjoying live music, drinking some port wine, and taking in views of the riverfront.

Go early to see Livraria Lello to beat the long lines and crowds. Advance tickets are highly recommended.

Grab coffee at the historic Cafe Majestic, a 1920s Art Nouveau cafe with a beautiful interior. A short walk away is the McDonald's Imperial, often referred to as the most beautiful McDonald's in the world. The interior has ornate crystal chandeliers and a wall of stained glass art. Some background – it used to be the classy Imperial Cafe, designed in the Art Deco style.

Visit the Capela das Almas church, a neoclassical building from the 18th century known for the gorgeous blue azulejo tiles on the exterior walls.

In the afternoon, take a walk across the Dom Luís I Bridge while enjoying incredible views of Porto. Take a tour at one of the port wine cellars in Gaia.

To watch the sunset, grab a bottle of wine and get one of the best views at Jardim do Morro. It's a lively atmosphere and a truly enjoyable experience as people start to clap when the sun goes down.

Embark on a highly recommended private Douro Valley tour, one of the highlights of my entire trip!

Start the day with a stop in the beautiful city of Amarante and explore its historical center. Continue to the picturesque Douro Valley, where you can appreciate its beauty, serenity, and terraces of vineyards known as the Stairs of the Giants, along with farms and villages along the hills.

Upon arriving in Pinhão, visit one of the most beautiful train stations in Portugal. Take a cruise to relax and enjoy the unique landscapes of the region.

Explore the charm of two renowned wine estates on this tour. Start at Quinta do Cume, a recently established family-owned winery. Tour the winery to learn about the vineyards and winemaking processes, then sample a diverse selection of wines. Continue on to Quinta do Seixo , the estate associated with the renowned Sandeman brand to try the famous port wines that Portugal is known for.

Fly to Madeira and upon arrival, pick up a rental car (highly recommended for island exploration). I recommend renting the smallest car suitable for your party, considering the very narrow streets throughout Madeira.

Evening Activity: Take the Monte cable car from Funchal to Monte for a thrilling toboggan ride down the mountain in a wicker basket! It's one of the most exciting commutes you'll ever take! Make sure that you have cash to purchase tickets.

Today you’ll take a picturesque road trip, winding through the stunning landscapes of Madeira. Begin your journey to the 25 Fontes Falls, a captivating hike with, as the name suggests, 25 waterfalls surrounded by lush greenery. Along the way, make stops to observe the Cabo Girao Skywalk, the highest sea cliff in Europe which offers panoramic views of the coastline. You’ll also see the Cascata dos Anjos, a dramatic waterfall that falls from a cliff and lands on a narrow coastal road below.

I recommend bringing lunch to enjoy after the hike amid the natural beauty of Madeira.

Continue your exploration by driving to the Porto Moniz Natural Swimming Pools. These natural pools, formed by volcanic lava rocks and filled with crystal-clear Atlantic seawater, provide a refreshing and scenic swimming experience. If you didn’t bring lunch, there are several restaurants right by the pools.

You can also visit nearby attractions, like Ilheus da Ribeira da Janela and the Véu da Noiva viewpoint, for some quick photo ops on your way back to Funchal.

Embark on the iconic Pico do Arieiro to Pico Ruivo hike, which is celebrated as the most beautiful and famous trek in Madeira. Rising above the clouds, this trail offers breathtaking vistas of rugged landscapes and panoramic views of the island. If you're an early riser, don't miss the most spectacular sunrise at the peak!

The roundtrip hike takes about six hours. For a more leisurely pace or if you prefer a one-way hike from Pico do Arieiro to Pico Ruivo (three hours), consider arranging a taxi for the return journey.

Get ready for an absolute blast with canyoning—an exciting and adrenaline-pumping way to explore the incredible landscapes of Madeira Island!

Picture yourself rappelling down waterfalls, swimming through crystal-clear pools, and soaking in breathtaking views, all while having a great time surrounded by nature's wonders.

Fly to Lisbon and then take the train or pick up a rental car to drive to Lagos (we chose to drive).

Since today will be a long travel day, take the rest of the day at your own pace. I suggest exploring the Old Town and grabbing dinner on the beach for a relaxing end to your day.

Book a guided kayak tour to the Benagil caves - a must see! The Benagil kayak tour is not just the best but also the most fun way to explore the Algarve coast and venture inside the beautiful sea caves of Benagil.

Admire impressive rock formations and beautiful beaches along the way. The tour concludes with a stop inside the iconic Benagil cave, where you can relax on a little beach.

After the tour, head back to Lagos and spend a leisurely afternoon at Praia de Batata.

Train or drive back to Lisbon after checking out of your hotel.

Make the most of your last day of sightseeing in Lisbon. Begin with a visit to the Belem Tower, arguably Lisbon's most iconic structure. This 16th-century defensive fort, strategically positioned along the Tagus River, served as a formidable barrier against enemy ships.

Next, explore the nearby Jeronimos Monastery, a UNESCO World Heritage Site housing chapels, cloisters, and the tombs of legendary Portuguese figures like Vasco da Gama.

And, of course, a visit to Belem wouldn't be complete without trying the famous Pasteis de Belem!

End your day at LX Factory, a transformed old industrial complex that has evolved into a hub of Lisbon's trendiest restaurants, bars, and shops.

Farewell to Portugal - Board your homeward-bound flight, carrying cherished memories of your time in Portugal.