Portugal's historic cities and unspoiled countryside take center stage on this 10-day, self-drive adventure. Heading north from Lisbon, you'll take your time exploring the hilltop villages of the Alentejo and the famed wine country of the Douro Valley before reaching riverside Porto and its vibrant culinary scene. Loop south again to make your way back to the capital at a leisurely pace—discovering medieval towns, fishing villages, and the wild Atlantic coastline along the way.


  • Get a taste for custard pastries & fado music in Lisbon
  • See living history at Évora's ancient university & Roman ruins 
  • Glide down the Douro River on a traditional wooden rabelo boat
  • Sample Porto's famous fortified wine on a cellar tour
  • Look out over crashing Atlantic surf from Nazaré's clifftop fort

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon Lisbon
Day 2 Discover Lisbon & the Belém Quarter, Fado Dinner Lisbon
Day 3 Pick Up Rental Car & Explore Cascais & Sintra  Lisbon
Day 4 Drive to Évora via Monsaraz Évora
Day 5 Drive to the Douro Valley via Tomar & Coimbra Douro Valley
Day 6 Douro Valley Wine Tasting & Boat Ride Douro Valley
Day 7 Drive to Porto via Guimarães & Braga  Porto
Day 8 Explore Porto, Port Wine Cellars & Tasting Experience Porto
Day 9 Drive to Lisbon via Batalha Monastery, Nazaré & Óbidos Lisbon
Day 10 Drive to Lisbon Airport & Depart  

Detailed Itinerary

Day 1: Arrive in Lisbon

The red rooftops of Lisbon's Alfama district

Welcome to Portugal! Upon arrival at Lisbon Airport, a private driver will be waiting to transfer you to your accommodation in the capital. Depending on your arrival time, spend the afternoon settling into your hotel or take a stroll around the Alfama district for quaint alleys, cathedrals, remains of the city walls, and great little cafés to sit and enjoy the sounds and sights of the city. As evening falls, enjoy a drink in Rossio Square or head to the Bairro Alto district for an authentic Portuguese meal.

Day 2: Discover Lisbon & the Belém Quarter, Fado Dinner

Hop on one of Lisbon's iconic trams to explore the city
Spend today exploring most of the Old Town of Lisbon, one of the world's oldest and most beautiful cities. Walk its narrow and hilly streets, admire its intricately tiled sidewalks, visit important historic sites, climb to panoramic viewpoints, and taste the delicious local gastronomy. You’ll also spend some time getting to know the Belém quarter, famous for its monuments from the age of the Portuguese Discoveries and one of the most renowned Portuguese delicacies, the pastel de Belém (custard tart).

As evening falls, head to a local restaurant to experience the splendor of Portugal's traditional music firsthand. Known for its haunting melodies, fado originated in the poorer quarters of Lisbon, singing of all the sadness, sorrow, and longing of day-to-day living. The band may have a variable number of performers but normally consists of a singer, a classical guitar player, and a fado guitar player. Tonight you'll immerse yourself in the beauty of this art form as you enjoy dinner serenaded by a soundtrack of live fado music. 

Day 3: Pick Up Rental Car & Explore Cascais & Sintra

Explore Cascais & Sintra (with Road Book)
The fairytale Pena Palace in Sintra
Today you'll pick up your rental car and start to explore the picturesque countryside and coastline around Lisbon at your own pace—starting with visits to Cascais, the former summer residence of the Portuguese royal family, and the luxurious seaside resort of Estoril.
Continue past the sweeping vistas of Cabo de Roca, the westernmost point of mainland Europe, and end your day trip in the fairytale village of Sintra. Set among the lush mountains and forests of Sintra-Cascais Natural Park, this UNESCO World Heritage Site is home to fantastical palaces and manor houses, including the iconic yellow Pena National Palace and the Castle of the Moors. Take your time exploring this remarkable area, then head back to Lisbon in time for dinner.

Day 4: Drive to Évora via Monsaraz

Évora's spectacular medieval cathedral

Today you'll leave Lisbon behind and hit the road, driving east across the plains of the Alentejo region towards the historic town of Évora. En route, you can choose to stop in Monsaraz, a fortified hilltop village that overlooks the Alqueva Dam and is rich in history and atmosphere. The tiny, whitewashed center is easy to explore, and its medieval castle offers amazing panoramic views of the town, plains, and lake below.

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Continue to Évora, where you'll get settled before heading out to explore. One of Portugal's oldest cities, this UNESCO World Heritage Site dates back to the Roman era and offers an abundance of beautiful architecture and sites. Marvel at the medieval architecture of the Évora Cathedral, go back in time with a visit to the 2000-year-old Templo Romano, and see one of the most fascinating (and morbid) structures in the world with a trip to the 16th-century Capela dos Ossos (Chapel of Bones). End your evening with a bite to eat and a drink in the bustling city square of Praça do Giraldo.

Day 5: Drive to the Douro Valley via Tomar & Coimbra

Baroque splendor in the University of Coimbra's library
Back on the road today, you'll head north towards the Douro Valley, stopping first in Tomar, known as the "Templar City." Here you can visit the UNESCO-listed, 12th-century Convento de Cristo, which was the historic headquarters of the Knights of Templar, as well as the 15th-century Tomar Synagogue, which became a haven for the Jewish population expelled from Spain in 1492.
Continue to nearby Coimbra, one of the most important cities in Portuguese history as well as the oldest. The former medieval capital is most famous for its 13th-century University of Coimbra, which is a great place to start your sightseeing. Bibliophiles will love its Baroque library, home to over 200,000 books and considered one of the most beautiful libraries in the world. Next door you'll find the intricately tiled Chapel of Saint Michael, and don't miss a scenic stroll through the historic center before continuing the Douro Valley for the evening.

Day 6: Douro Valley Wine Tasting & Boat Ride

Vineyards along the Douro River
Spend today discovering the fertile wine country of the Douro Valley. Home to the country's legendary Port wine, the region is famous for its dramatic landscapes, where vineyards cling to terraces carved into steep hillsides along the Douro River. Go for a hike among the vines, visit historic quintas (estates/wineries), and stop for some tastings of the local vintages. Later on, you'll experience this UNESCO-listed region in the best way possible—gliding along the river in an authentic wooden rabelo boat as you pass the golden-green vineyards of the world's first demarcated wine region.

Day 7: Drive to Porto via Guimarães & Braga 

The beautifully-tiled Chapel of St Francis in Guimarães 
Today takes you west to the small city of Guimarães, considered the cradle of the Portuguese Nation and the birthplace of its first king, D. Afonso Henriques. Among its exquisite medieval center, don't miss the imposing Guimarães Castle, the Dukes of Bragança Palace, and the church of Santa Maria da Oliveira.
Proceed to Braga to discover Roman ruins, stately Baroque churches, and solares (manor houses), as well as two of Portugal's most important pilgrimage sites: the UNESCO-listed Bom Jesus with its soaring, allegorical stairway, and the serene hilltop sanctuary of Sameiro. After you've had your fill of sightseeing, get back on the road and continue to Porto for the evening. 

Day 8: Explore Porto, Port Wine Cellars & Tasting Experience

Traditional fishing boats along Porto's riverfront
Head out on your own today to immerse yourself in the colorful neighborhoods and rich history of Porto. Stroll through the cobblestone lanes of the UNESCO-listed Ribeira district, admire soaring Gothic churches, wander the bustling stalls of world-class food markets, and climb to breathtaking views over the Douro River. In the afternoon, you'll join a guided tour of the cellars of Casa Ferreirinha, producer of Barca Velha and the city's famous Port wines for an immersive tasting experience.

Day 9: Drive to Lisbon via Batalha Monastery, Nazaré & Óbidos

Nazaré's clifftop fort and lighthouse

As you work your way back towards Lisbon today, stop first in Batalha, worth a visit for its magnificent 14th-century Batalha Monastery (officially known as the Mosteiro de Santa Maria da Vitória). This epic building is a masterpiece of Portuguese Gothic architecture, specifically the late Flamboyant style, and is designated a UNESCO World Heritage Site. 

Head to the coast next to break for a memorable lunch of fresh grilled fish in Nazaré. Located on a sweeping stretch of beach, this small fishing town is known for its stately shrine of Santuário de Nossa Senhora da Nazaré, as well as holding the record for the highest waves ever surfed. Take a walk to the 16th-century clifftop fort of São Miguel Arcanjo Fort after lunch to see some of the crashing waves up close.

Nearing Lisbon, you'll reach Óbidos, a fortified village in Portugal's Estremadura region that dates back to the Middle Ages. This fascinating historic site is filled with picturesque houses bordered by an imposing Moorish wall, and is known as Vila das Rainhas or "Town of the Queens." Take a walk through its cobblestone streets, climb its intact ancient fortifying wall, and try the local delicacy of ginginha—a sour cherry liquor often served in a chocolate cup.

Day 10: Drive to Lisbon Airport & Depart

Sunset over Lisbon's Abril Bridge

After a final leisurely breakfast, you'll make your way to the Lisbon Airport to drop off your rental car and catch your departing flight. Safe travels and boa viagem!

More Great 10-Day Portugal Itineraries

Looking for more inspiration for your trip to Portugal? Check out these other 10-day Portugal itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights.  


Map of Portugal Road Trip: Lisbon, Évora, Douro & Porto - 10 Days
Map of Portugal Road Trip: Lisbon, Évora, Douro & Porto - 10 Days