Explore the Charm of Southern Portugal in 5 Days

Visiting Southern Portugal and looking for the perfect itinerary that allows you to experience the region’s breathtaking landscapes and vibrant culture? You’re in the right place.

Here’s an epic 5 days in South Portugal itinerary that allows you to indulge in the region’s unique charm, from the bustling streets of Lisbon and the castle-filled lanes of Sintra to the deliciousness of Portuguese tarts, and the serene beauty of the Algarve coast.

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Best 5 Days Itinerary for Southern Portugal

South Portugal Day 1: Discover Historic Lisbon

Start your 5-day Southern Portugal journey in Lisbon, the capital of Portugal and one of the oldest cities in Europe. 

Where to stay in Lisbon: Hotel da Baixa | Montebelo Lisbon Downtown Apartments

Discover the heart of Lisbon

Begin your first day in Lisbon at Praca do Comercio, a grand square by the Tagus River perfect for a leisurely stroll. 

Enjoy the riverside ambiance and snap photos of the impressive triumphal archway, Arco Rua Augusta. Climb up the arch for gorgeous views of the city and the riverside.

Head towards the lively neighborhoods of Chiado and Baixa for a mix of shopping, historic sites, and charming cafes. 

Don’t miss the Santa Justa Elevator for panoramic city views.

📖 Read Next: How to plan 2 perfect days in Lisbon?

Explore Alfama and Tram 28

Stroll through the cobbled lanes of Alfama, Lisbon’s oldest district. 

Visit the Lisbon Cathedral (Sé de Lisboa) and admire the views from one of the miradouros that dot this historic neighborhood. 

Visit Sao Jorge Castle for rich insights into Lisbon’s history. 

Take a ride on Tram 28, the antique, yellow tram that snakes its way through the winding lanes. 

Combine an Alfama walking tour with a Tram 28 ride for a quintessential Lisbon experience.

📖 Read Next: 14 Best Things to Do in Alfama Lisbon

Enjoy a Fado show

End your day with an authentic Fado show, a traditional Portuguese music genre known for its soulful and melancholy tunes.

Several venues in Alfama offer dinner and Fado performances, providing an immersive cultural experience. This Alfama Tour and Live Fado with Traditional Dinner Experience is especially popular.

South Portugal Day 2: Discover Belem’s Architectural Marvels

Dedicate your second day to exploring Belem, a neighborhood as old as Portugal’s Age of Discoveries. 

It was from Belem that many explorers, including the famous Vasco da Gama and Pedro Alvares Cabral, set sail. You can find abundant traces of Portugal’s maritime history in the monuments of Belem, including a magnificent architectural style that developed during this time. It was called the Manueline style.

Marvel at the Manueline Monuments of Belem

Admire the stunning Manueline architecture of the Jeronimos Monastery, a UNESCO World Heritage site, and learn about the monument’s history. 

Constructed in the late 15th century, Jeronimos Monastery was dedicated to Vasco da Gama’s first journey, which discovered the marine route to India. Today, the monastery houses Vasco da Gama’s tomb as well as the tombs of Portuguese kings Manuel I and John III. 

The monastery’s cloisters (you must pay a fee to enter them) are exemplary of Manueline architecture. 

Climb up the Belem Tower, an iconic fortress that offers captivating views of the Tagus River. It served as the Portuguese lighthouse, customs house, and even a prison for a long time.

Visit the Monument of Discoveries – a Lisbon landmark built to commemorate the explorers who played pivotal roles in the Portuguese Age of Discovery.

Check out Belem’s eclectic museums

Belem is also home to several renowned museums, such as the National Archeological Museum, Coaches Museum, and MAAT (Museum of Art, Architecture, and Technology).

Relish a delicious Portuguese tart

No visit to Belem is complete without tasting the famous Pasteis de Belem. These delectable custard tarts are best enjoyed fresh from the oven at their original bakery by the same name. It is located right next to the Jeronimos Monastery.

✦ Pro Tip: Try this Pastel de Nata Baking Class in Lisbon.

South Portugal Day 3: Discover the Castletown of Sintra

Venture out of Lisbon for a day trip to Sintra, a picturesque town filled with fairytale castles and palaces. 

Tour the castles of Sintra

Head to the colorful Pena Palace perched atop a hill. Once the summer residence of the Portuguese royal family, the palace is home to ornate staterooms, vibrantly-colored terraces that offer breathtaking views, and whimsical architectural elements such as mythical creatures. Pena Palace is always the highlight of every Sintra trip.

Hike the fort walls of the Moorish Castle and visit the Sintra National Palace, a well-preserved medieval royal residence known for its beautiful tiled walls and magnificent living quarters.

Visit Quinta da Regaleira for its mysterious initiation wells, hidden caves, and enchanting gardens.

✦ Pro Tip: Book this Full-Day Guided Tour of Sintra from Lisbon.

Feast on Portuguese sweet treats 

Try the local specialty, travesseiros, a delicious puff pastry with almond filling, at Casa Piriquita, one of Sintra’s historic cafes.

Visit Europe’s southernmost point

Visit Cabo da Roca, the westernmost point of mainland Europe, to wrap up your trip to Sintra. 

Standing on the rugged cliffs, you’ll be treated to stunning views of the Atlantic Ocean and feel the power of the sea below as the waves crash against the rocks.

South Portugal Day 4: Explore Algarve’s Coastal Wonders

Travel to the Algarve region, known for its pristine beaches and stunning coastal landscapes. Make Lagos your base for the next two days.

Where to stay in Lagos – Quinta do Baia | Lagos Atlantic Hotel

Explore the stunning Benagil Caves

Take a boat tour from Lagos to marvel at the spectacular sea caves of Benagil, accessible only by water. 

A beautiful dome-shaped rock cave encloses a slight stretch of beach within it. An opening on the top filters sunlight from the top, making the Benagil Caves the most picturesque in the world.

✦ Pro Tip: Book this highest-rated Benagil Caves Speedboat Adventure from Lagos.

Marvel at Praia da Marinha

Next, head to Praia da Marinha and relax on one of the most beautiful beaches in the world, voted by CNN and Lonely Planet.

Dramatic cliffs, soft golden sands, and crystal-clear waters characterize Praia da Marinha. 

Perhaps the most photographed highlight of Praia da Marinha is the Cathedral Rock, shaped like an M. From the top of the cliff, this rock looks like a heart. If you’re visiting Portugal with your loved one, this might be the perfect place to pop the question.

South Portugal Day 5: Relax in Lagos

Spend your final day 5 in Southern Portugal, exploring the charming city of Lagos and enjoying its nearby beaches.

Experience the charm of Lagos

Wander through the cobbled streets of Lagos dotted with whitewashed houses, trendy cafes, and boutique stores. 

Visit the Church of Santo Antonio in the historic center and check out the ancient city walls.

✦ Pro Tip: Join this 3-hour Algarve classic food tour or bake your Pastel de Nata at this immersive workshop in Lagos.

Relax on the beach

Unwind on the golden sands of Praia Dona Ana or Praia do Camilo, both renowned for their stunning scenery.

Visit Ponta da Piedade

If you want a more dramatic beach experience in Southern Portugal, head to Ponta da Piedade and explore its towering rock formations, hidden caves, and grottos. 

Ponta de Piedade is one of the best places to enjoy a glorious Portuguese sunset by the sea. 

Visit Ponta da Piedade on a weekday to avoid crowds. Wear sturdy shoes to prevent slipping on the rocks. 

✦ Pro Tip: I recommend taking a boat tour because they take you deep inside hidden grottos and secluded beaches, which you cannot see otherwise. A guided kayak tour is also a great idea if you’re looking for something more adventurous.

Southern Portugal Travel Tips

• The best times to visit Southern Portugal are in spring (March to June) and fall (September to November), when there is pleasant weather and fewer crowds.

• To avoid long lines, book your tickets for popular attractions like Pena Palace, Quinta da Regaleira, Jeronimos Monastery, and Belem Tower ahead of time. Get a Lisbon Card to save $$ on entrance fees for historical landmarks.

• You’ll want to utilize the efficient and affordable public transportation options, including trains, trams, and buses, especially within Lisbon and Sintra, which have narrow, hilly lanes. The Lisbon Card also saves on transportation costs.

• Bring comfortable walking shoes to explore Lisbon’s Alfama neighborhood and Sintra’s historic district on foot.

• The sun can be intense, especially in summer. Always carry a water bottle to stay hydrated, particularly if you plan on engaging in outdoor activities.