Adventurous and independent travelers will love this 11-day itinerary that takes you on the road through Portugal's fascinating history and epic landscape. You'll spend some time exploring Lisbon, one of the oldest cities in the world, before driving north to Évora, where you will find prehistoric sites and towns fit for queens. You'll then head back down south to the Algarve, where you'll be blown away by the wild ruggedness and incredible beaches of southern Portugal's famous coastline.


  • Try a pastel de nata in Lisbon's famous Belém neighborhood
  • See fairytale castles in Sintra
  • Keep your cool in Évora's spooky Chapel of Bones
  • Catch some waves off the Algarve coast

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon Lisbon
Day 2 Visit Lisbon's Old Town Lisbon
Day 3 Explore Belém, Pick Up Rental Car & Visit Cascais Lisbon
Day 4 Discover Magical Sintra Lisbon
Day 5 Drive to Óbidos, the Town of Queens Évora
Day 6 Drive to the Ancient Roman City of Évora Évora
Day 7 Drive to the Wild & Beautiful Algarve Coast Algarve
Days 8-9 Explore the Beaches & Villages of the Algarve Algarve
Day 10 Enjoy Your Time in the Algarve & Drive Back to Lisbon Lisbon
Day 11 Depart from Lisbon  

Detailed Itinerary

Day 1: Arrive in Lisbon

Lisbon old town at sunset
A view of Lisbon's Old Town during sunset

Upon your arrival to Lisbon, a driver will be waiting to take you to your accommodations in the city. Once there, enjoy some free time and explore Portugal's capital, which is one of the oldest cities in the world. In fact, Lisbon is the second oldest capital city of Europe (after Athens). The line between the ancient and the modern can be thin here, which is just one of the many unique elements of this coastal center. 

There are amazing activities and sights for travelers of all kinds. You can get lost in the stacks of Livraria Bertrand, the world's oldest bookstore still in operation or marvel at the intricate blue tiles at the Museu Nacional do Azulejo (The National Tile Museum). Perhaps you'll want to grab a drink at a local bar to listen to some live fado music or if you're feeling peckish, head over to Pastéis de Belém to try an original pastel de nata (or three), whose secret recipe has remained safely guarded by the owners of the bakery since 1834.

Day 2: Visit Lisbon's Old Town

Visit Lisbon's Old Town (With Road Book)
The skyline of Lisbon's magical Alfama district
Explore Alfama or the Old Town of Lisbon, one of the most beautiful cities in the world! Situated underneath the Castelo de São Jorge, this neighborhood is a maze of winding, hilly streets, tiled sidewalks, and historical monuments and sites like the 17th-century Church of Santa Engrácia and the Judiaria or the Jewish Quarter.

Buy gifts for loved ones at the Feira da Ladra flea market, which is the biggest in the city. Make your way to a miradouro or one of the many viewpoints, which offer stunning panoramic views of Lisbon. Don't forget to replenish yourself with some of Lisbon's delicious local gastronomy.

Day 3: Explore Belém, Pick Up Rental Car & Visit Cascais

Explore Belém and Cascais  (With Road Book)
The beautiful Tower of Belém during sunset
Today, you'll visit the Belém quarter in Lisbon, which you can explore at your own pace. Belém is famous for its monuments from the Age of Discoveries (spanning from the 15th to 16th centuries), as well as for its renowned delicacy: pastéis de Belém. Among the neighborhood's many highlights, you'll find the majestic Jeronimos Monastery and the impressive Belém Tower, which is seen as a symbol of Lisbon.

After you get your fill of Belém, you can pick up your rental car and drive to Cascais, a small coastal town nearby that's surrounded by beautiful landscapes. Cascais lies on a stretch of coast, where small sandy beaches, rocky cliffs, and picturesque houses combine to form a true picture-postcard image. Historically, Cascais was a haven for the Portuguese and European aristocracy, and was where the Portuguese royal family had their summer home.

If you're looking for an epic experience of nature, check out the cliffs of Boca do Inforno (Hell's Mouth), which offer a dramatic view to the sea, particularly when the waves bash against them.

Day 4: Discover Magical Sintra

Discover Magical Sintra (With Road Book)
Pena Palace perched high in the hills of Sintra
Today you’ll visit Sintra, which is a UNESCO World Heritage village that's set in a small mountain. Consider starting the day with a visit to Guincho, the beach area that serves as a gate to the Sintra Cascais Natural Park. In this natural park, you'll find sprawling manors and palatial houses nestled among lush forest. You'll also discover a number of castles like the iconic Pena Palace that's out of a fairytale, and the Quinta da Regaleira, which includes an inverted tower that was used for initiation rites and ceremonies for the Knights of Templar. 

After visiting Sintra, you can continue north to the cape of Cabo da Roca, which is the westernmost point of continental Europe and is known as the "edge of the world." There, you can experience the feeling of being at the end of the world at the 18th-century lighthouse. End your day further north at Azenhas do Mar, which is a postcard village perched on cliffs overlooking the Atlantic, before returning to Lisbon.

Day 5: Drive to Óbidos, the Town of Queens

Drive to Óbidos, the Town of Queens (With Road Book)
The old Moorish wall that borders the fortified village of Óbidos
Today, you'll drive north to Óbidos, which is a fortified village from the Middle Ages filled with picturesque houses that are bordered by a Moorish wall. In fact, it's so charming that it was gifted to Queen Urraca in 1210 and since then, has been given to a number of queens, which gives the town its nickname Vila das Rainhas or "Town of the Queens." You can explore Óbidos by walking its cobblestone streets, climbing its ancient fortifying wall, and trying Ginginha, a sour cherry liquor that's often served in a chocolate cup.
Plan your trip to Portugal
Chat with a local specialist who can help organize your trip.
If you're curious about exploring other sites near Óbidos, you can drive north to visit the town of Batalha, where you can see the magnificent 14th-century Gothic Batalha Monastery. Another fantastic area to explore near Óbidos is Tomar, the "Templar City" that includes the 12th-century Convento de Cristo, which was the headquarters of the Knights of Templar.

Day 6: Drive to the Ancient Roman City of Évora

Drive to the Ancient Roman City of Évora (With Road Book)
The impressive Gothic exterior of the Évora Cathedral
Explore the historic city center of Évora, which is a UNESCO Heritage Site. One of Portugal's oldest cities that dates back to the Roman era, Évora is situated in the countryside of the Alentejo region. This small city offers an abundance of sites, such as the Gothic-style Évora Cathedral and the 2000-year-old Templo Romano (Roman Temple). Don't forget to stop by the 16th-century Capela dos Ossos (Chapel of Bones), one of the most fascinating (and morbid) structures in the world.
If you want to go even further back in time, consider driving to the nearby Cromeleque dos Almendres (Cromlech of the Almendres), a prehistoric site that goes back to the 6th Millennium BCE. Here, you can see monoliths arranged in a geometric formation, which is one of the largest megalithic structures in Europe and the most important on the Iberian Peninsula. 

Day 7: Drive to the Wild & Beautiful Algarve Coast

View of the sea from Lagoa
A clear view of the sea from Lagos
Today, you'll drive south to the Algarve. You can choose between taking the fastest route, so you can have more time in the Algarve, or a more scenic route, which will give you the option of visiting sites like Monsaraz and Mértola along the way.
Monsaraz is a fortified hilltop village above the Alqueva Dam, which offers amazing panoramic views from its medieval castle. You have another option of driving down to Mértola, an important settlement during the Moorish occupation of Portugal. Mértola has become known as a "museum town" thanks to its different monuments that have been transformed into museums, such as the Castle of Mértola and Paleo-Christian Basilica.

Before reaching the Algarve, you also have the choice of making a detour to see the whitewater rapids of the Pulo do Lobo. This is set against the rugged backdrop of the Parque Natural Vale do Guadiana (Guadiana Valley Natural Park) and will be sure to inspire awe.

Days 8-9: Explore the Beaches & Villages of the Algarve

Explore the Beauty of the Algarve
The Benagil Caves offer stunning views and formations
The next two days are free for you to explore Portugal's celebrated southern coast at your leisure. This area is perfect for nature-lovers, history buffs, and everyone in between, as it offers something for every type of traveler. The Algarve is known for its dramatic beauty, wild and rugged landscapes, and of course, its beaches (and surfing). You can discover firsthand why this gem of Portugal has won the "best beach destination" award at the World Tourism Awards so many times. 
During this portion of your trip, you have the option of arranging for surfing lessons in one of the most famous surfing locations in the world. Other highlights in the Algarve include wandering the quaint historical towns of Tavira, Lagos, and Silves or encountering diverse wildlife and nature along the Parque Natural da Costa Vicentina and the cliffs of Sagres or Ponta da Piedade in Lagos.

Day 10: Enjoy Your Time in the Algarve & Drive Back to Lisbon

Enjoy Your Time in the Algarve and Drive Back to Lisbon
Catch the sunset in the Algarve
Enjoy the rest of your time in the Algarve, before heading back to Lisbon. Perhaps you'll want to grab a fresh seafood meal, catch some waves, or connect with history in one of the region's many interesting sites like the Old Town of Faro or the blue-tiled church of Igreja de Sao Lourenco de Almancil. This is a day for you to move at your leisure, so when you've gotten your fill of the Algarve, drive back to Lisbon.

Day 11: Depart From Lisbon

Depart Lisbon
A plate of mind-blowing pastel de nata
If you have free time before departure, enjoy your time in Lisbon, where you can go for a walk, see any sites that you missed before, or eat more Portuguese delicacies. When you're ready, head to the airport for your departure. Safe travels and boa viagem!

More Great 11-Day Portugal Itineraries

Looking for more inspiration for your trip to Portugal? Check out these other 11-day Portugal itineraries, with outdoor activities, cultural trips, and best-of tours to hit the highlights.


Map of Self-Drive Portugal: Lisbon, Évora & the Algarve - 11 Days
Map of Self-Drive Portugal: Lisbon, Évora & the Algarve - 11 Days