Day 1: Lisbon – Exploring the Capital
Lisbon is where most travelers start their trip in Portugal. It’s a vibrant city filled with history, great food, and stunning viewpoints.
Start your morning by visiting the iconic Belém Tower. It’s a UNESCO World Heritage site that offers a glimpse into Lisbon’s maritime past. Close by is the Jerónimos Monastery, another historical gem that should not be missed.
Afterward, grab some local pastries at Pastéis de Belém. Their centuries-old recipe makes for the best pastéis de nata, the famous Portuguese custard tarts. You won’t find a better version of this treat anywhere else.
Next, head towards the Alfama district. This is the oldest neighborhood in Lisbon, known for its narrow streets and colorful houses. It’s a great place to wander around. Don’t miss the São Jorge Castle, perched on a hilltop, offering a great view of the city.
For lunch, stop at Time Out Market. It’s a large market with multiple food stalls where you can try a variety of local dishes without overcommitting to just one option.
In the afternoon, walk down the Baixa and Chiado districts for some shopping or people-watching at one of the many charming cafés. To end your day, take the historic No. 28 tram up to Miradouro da Senhora do Monte for a fantastic sunset view over Lisbon.
Where to Stay
If you’re looking for a budget stay, Lisbon Calling Hostel is a great option. For a more boutique experience, consider The Lumiares. It’s centrally located and beautifully designed.
Day 2: Sintra and Cascais – Palaces and Coastal Views
Just a short 40-minute train ride from Lisbon is the magical town of Sintra. This UNESCO-listed town was once the summer retreat for Portuguese royalty, and it’s full of fantastic palaces and gardens.
Your first stop should be the Pena Palace, a colorful and whimsical palace offering a stunning view of both the Atlantic Ocean and the surrounding parks. From here, take a walk or a quick bus ride to the Moorish Castle. It’s mostly ruins, but the views are incredible. You can also explore the walls and get a sense of how strategically important this site once was.
Next, visit the Quinta da Regaleira. It’s an enchanting, somewhat eccentric estate featuring a mix of Gothic, Renaissance, and Manueline architecture. The gardens are full of hidden treasures like grottos and the iconic Initiation Well.
After lunch in town, hop on a quick train or bus to Cascais, a beautiful seaside town. This town is perfect for a relaxing stroll along the beach. If the weather is nice, take a dip in the Atlantic Ocean. You can have some gelato while taking in the slow-paced, idyllic coastal life.
One final stop to consider: Boca do Inferno (“Mouth of Hell”). It’s a rugged cliff formation right by the sea where the waves crash dramatically, providing awe-inspiring views.
Where to Stay
For Sintra, book a room at Tivoli Palácio de Seteais for a luxurious experience or choose Moon Hill Hostel for a more budget-friendly stay. In Cascais, Villa Cascais offers stunning oceanfront views.
Day 3: Porto – The Heart of Northern Portugal
In just under three hours by train, you’ll arrive in the lively, romantic city of Porto. Known for its famous port wine and charming streets, Porto is a must-see.
Begin in the Ribeira district, where you’ll find narrow cobbled streets that lead down to the riverfront. It’s a busy area with lots of outdoor cafés and restaurants. The pastel-colored buildings here are postcard-worthy.
Cross the Dom Luís I Bridge, an engineering marvel that connects Porto to the city of Villa Nova de Gaia. On the other side, you’ll find all the port wine cellars. Many of them offer tastings. I recommend stopping by Taylor’s, one of the most renowned cellars in the area.
Take the afternoon to visit the Clérigos Tower. Climb the 225 steps for a panoramic view of Porto. Afterward, stop by the stunning Lello Bookshop. If you’re a Harry Potter fan, you’ll appreciate that this shop inspired J.K. Rowling during her time in Porto.
End your day with a traditional francesinha sandwich, a local specialty made with multiple meats, cheese, and a spicy sauce. Nothing better after a day of exploring.
Where to Stay
For budget travelers, The House of Sandeman Hostel is a great option. If you want something more upscale, try Ribeira do Porto Hotel for amazing views of the river.
Day 4: Douro Valley – Wine Tasting and River Views
Today, explore the beautiful Douro Valley, just a two-hour drive or day tour away from Porto. This region is famous for its terraced vineyards that stretch along the Douro River, and it’s one of the oldest wine regions in the world.
Booking a wine tour is the perfect way to make the most of your day here. Many tours include visits to local wineries where you can taste both port and still wines. Some offer boat rides down the river, giving you incredible views of the surrounding vineyards.
If you’d rather explore on your own, rent a car or take a scenic train ride from Porto to Pinhão. Once you’re in the heart of the Douro Valley, visit a few wineries, such as Quinta do Bomfim or Quinta da Pacheca.
For lunch, stop at a local restaurant and try the region’s specialties, like grilled meats or seafood dishes, paired with local wine.
In the later afternoon, take a leisurely cruise on the Douro River. It’s a relaxing way to wind down your day in one of the most picturesque regions of Portugal.
Where to Stay
If you want to spend the night in the Douro Valley, consider staying at Quinta da Pacheca Hotel or DOC Douro Valley Wine Hotel. Both offer comfortable stays with stunning views.
Day 5: Coimbra – Portugal’s Historic University Town
On your way back south, stop at the charming city of Coimbra. Once the capital of Portugal, Coimbra is famous for its university, one of the oldest in Europe.
Start your day at the University of Coimbra. Spend time exploring its famous Joanina Library, which is often considered one of the most beautiful libraries in the world. The university grounds also offer a great view of the city.
Next, explore the Old Cathedral (Sé Velha). It’s a Romanesque church located in the heart of the old town and serves as a beautiful reminder of Coimbra’s medieval past. From there, take a stroll down the Rua Ferreira Borges, a pedestrian street lined with shops and cafés. Coimbra’s old town has a unique charm that will make you fall in love with its narrow streets and vibrant energy.
For a break, stop at a café along the Mondego River. It’s a nice, calm spot that contrasts with the hustle of the city center. Nearby, you can also visit the Santa Clara-a-Velha Monastery, which dates back to the 14th century.
In the afternoon, explore the Botanical Gardens. They’re part of the university and are a peaceful escape from the heat and busyness of the town.
Finally, head up to the Pedro e Inês footbridge, a great spot to take in a sunset over the river and city.
Where to Stay
If you choose to stay in Coimbra for the night, consider Hotel Astoria for a more old-world charm or opt for Optimus Hostel for something on the budget-friendly side.
Final Thoughts
Portugal offers such a rich mix of history, culture, wine, and food. This itinerary gives you a well-rounded snapshot of what the country has to offer. Five days won’t capture it all, but this route will give you an incredible first taste. Take it slow and enjoy every moment.
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