This two-week Portuguese odyssey combines cities, countryside, and coast for a road trip to remember. Savor traditional cuisine in Lisbon, lose yourself in the riverside neighborhoods of Porto, explore vineyards and cork forests around Évora, and soak up some sun on the golden beaches of Lagos. Along the way, a series of guided tours introduce you to the culture and customs of each city, while plenty of downtown means you can cut loose and choose your own adventure on day trips.


  • Hop on a cable car & hear authentic Fado music in Lisbon
  • Take a day trip to Sintra, Cascais & Estoril
  • Wander the historic neighborhoods of Porto
  • Go wine tasting & river cruising in the Douro Valley
  • Discover the maritime history of UNESCO-listed Évora
  • Relax on the breathtaking beaches of the Algarve 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon Lisbon
Day 2 Get to Know Lisbon - Half-Day Tour Lisbon
Day 3 Day Trip to Sintra, Cascais & Estoril Lisbon
Day 4 Explore Lisbon & Surroundings Lisbon
Day 5 Drive to Porto, via Coimbra Lisbon
Day 6 Get to Know Porto - Half-Day Tour Porto
Day 7 Day Trip to the Douro Valley Porto
Day 8 Explore Porto & Northern Portugal Porto
Day 9 Drive to Évora, Afternoon Tour Évora
Day 10 Explore Évora & the Alentejo  Évora
Day 11 Drive to Lagos Lagos
Days 12 & 13 Explore Lagos & the Algarve Lagos
Day 14 Drive to Lisbon & Departure  

Detailed Itinerary

Day 1: Arrive in Lisbon

Welcome to Lisbon

Welcome to Portugal!

After touching down at the airport in Lisbon, collect your rental car and head to your hotel. After checking in, you'll have as much time as you'd like to unwind after your long journey. 

You'll find Lisbon to be an unheralded gem of a European capital. The hilly waterfront neighborhoods are dotted with grand plazas and pastel-colored buildings, many of which date back hundreds of years. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the highest points in the city. In their heyday, they served as defensive outposts protecting the Port of Lisbon and all those Portuguese galleons returning from the New World laden with pilfered gold and silver.

The quickest way to acquaint yourself with Lisbon's culture is through its traditional cuisine. This includes pastéis de bacalhau (cod fritters), grilled sardines, squid stuffed with sausage and onions, queijo de azeitão (a creamy cheese made from sheep's milk), pastéis de nata (egg custard tarts), and the quintessential street food, the bifana. This sandwich of pork marinated in white wine is pure heaven after one too many Vinho Verdes.

Day 2: Get to Know Lisbon - Half-Day Tour

Streets of Lisbon
The hilly streets of Lisbon

After breakfast, your private guide will pick you up at your hotel for an excursion around Lisbon. Your first stop is the beautiful area of Belém, an ode to the superb age of the Portuguese Discoveries—the numerous territories and maritime routes discovered by the Portuguese during the 15th and 16th centuries. Here you'll visit Belém Tower and the Monument to the Discoveries, followed by the magnificent Jerónimos Monastery, considered one of the most stunning monuments of Portugal. 

Next, you will proceed to the charismatic Alfama district, home of traditional Fado music, with twisting streets that wind up to an imposing castle on one of the city’s highest hills. With whitewashed houses, flower-laden balconies, and red-tiles roofs, Alfama is a perfect mix of historical landmarks and charming residences. You will also discover one of the most important squares in the city and the famous Liberdade Avenue. Make sure to taste the delicious and sweet pastel de Belem, a traditional pastry found here. 

At the end of the tour, your guide will return you to your hotel. As for dinner, consider choosing between some of the city's best Fado restaurants for a memorable evening of traditional cuisine and music. 

Day 3: Day Trip to Sintra, Cascais & Estoril

Sintra's fairytale-style Palácio da Pena

The area surrounding Lisbon offers an incredible variety of architecture and scenery, from fairytale palaces to romantic towns and breathtaking viewpoints. Today's guided excursion is the ideal way to experience some of these attractions. 

After breakfast at your hotel, your guide will deliver you to the first stop on the tour: Sintra. This village—about 30 minutes by car from the capital—is a harmonic combination of history and fantasy, described as a “glorious Eden” by the British poet Lord Byron in the 18th century. You will have free time to explore on your own and have lunch, and your guide can recommend some imposing monuments and wonderful palaces that are worth a visit. 

Your next stop will be the Cabo da Roca, the westernmost point of Portugal and mainland Europe. Enjoy gorgeous views across the Atlantic Ocean as waves crash onto the shore. On the return trip to Lisbon, you will have time to appreciate the fishing harbor and tourist center of Cascais, the former summer residence of the Portuguese royal family, and nowadays an excellent spot for surfing. You'll also be able to visit the luxury entertainment town of Estoril, known for its casino (the largest in Europe) and attractive gardens. 

After the excursion, you'll have the remainder of the day to enjoy Lisbon any way you'd like.

Day 4: Explore Lisbon & Surroundings

Medieval fortress walls in Óbidos

Today, you'll have a free day in Lisbon to enjoy any way you'd like! If you've seen enough of the city and are anxious to explore other areas, hop in your rental car and make the most of these excellent day-trip ideas:

  • Fátima & Nazaré: Religiously significant, Fatimá is the site of an important Catholic shrine, Our Lady of Fatima. From there you'll continue to the coastal town of Nazaré for a completely different type of sightseeing: the site of the biggest wave ever surfed.

  • Jeronimos Monastery: This glorious example of ancient architecture was listed as a UNESCO World Heritage Site in 1983. Located near the Tagus River, the monastery was commissioned in the late 15th century by King Manuel I, to honor Our Lady and Saint Jerome.

  • Sesimbra: This is a great village to stroll along the beach and just watch the world go by. You can also pay a visit to Sesimbra's beautifully-restored central church, or head uphill to Sesimbra Castle. If you have time on the way back, you can also make a stop in Almada for spectacular views over Lisbon.

  • Óbidos: The historical medieval village of Óbidos definitely merits its own day trip. Surely one of the best-preserved old towns in Portugal, visitors will be delighted by its cobbled streets and sunnily painted houses.

  • Arrábida Natural Park: For something more active, take a kayaking trip in Arrábida Natural Park and admire the gorgeous views from the water as you paddle through its tranquil river systems. You’ll have the chance to discover numerous hidden caves and secluded beaches—don't forget to bring along a picnic lunch.

  • Knights Templar: Visit the villages of Constância and Tomar to learn about the intriguing story of this holy order of warrior monks.

Day 5: Drive to Porto, via Coimbra

Porto's scenic riverfront

After breakfast, check out and set off in your rental car for a road trip north. Your ultimate destination is the city of Porto but after two hours you'll stop en route in Coimbra. This is one of the most stunning cities in Portugal, which is why it's a shame that many visitors overlook it on their way from Lisbon to Porto.

Upon arrival in Coimbra, take a few hours to explore. The city served as the medieval capital of Portugal for over a hundred years, and has hosted the country’s greatest university for the past five centuries, Coimbra wears its weighty importance in Portuguese history with dignity. Its atmospheric, beautiful historic core cascades down a hillside in a lovely setting on the east bank of the Rio Mondego, with its multicolored collage of buildings spanning nearly a millennium. Don't miss the medieval old town and Sé Velha, a Romanesque cathedral dating to the 12th century. 

After lunch, it's time to get back on the road and continue to Porto, where you'll have the rest of the afternoon to explore the city at your leisure.

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Day 6: Get to Know Porto, Half-Day Tour

Porto's historic Foz neighborhood

Today is a great introduction to Porto! After breakfast at the hotel, you'll join a half-day tour of the city with a local guide. This excursion will lead you through the most important landmarks of Portugal’s second most populous city as you travel from place to place in a comfortable private vehicle. 

Your guide will explain the rich history of this city, also called Invicta (the Unbeaten City), with stories of heroes and battles, as you make your way to the trendiest and most cultural area of the city. Here you'll explore Boavista Avenue, one of the city's most important streets, and Foz, home to some of the most important museums and modern local treasures.

Next, you'll head to the city center—a UNESCO World Heritage Site—to admire the most renowned Romanesque, Gothic, Baroque and Neo-Classical monuments and sites, including the São Bento Railway Station, Clerigos Tower, Church of St. Francis, Lello Bookshop, St. Catarina Street, Majestic Café, and Bolhão Market, to name a few.

After visiting the imposing Porto Cathedral with its superb silver altarpiece, you will finish the tour along the banks of the immense Douro River with views of Ribeira Plaza and the D. Luís Bridge

Day 7: Day Trip to the Douro Valley

Douro Valley
A winery in the lush Douro Valley

Discover the Douro Valley today, a fertile grape-growing region that produces some of Portugal's best wines. Your guide and driver will pick you up in Porto for the 1.5-hour trip outside the city to the heart of the region.

This full-day tour includes a visit to a quinta (winery) where you'll tour the vineyards and production facilities, and enjoy a wine tasting. You will then drive to a nearby country town where your guide will recommend the perfect restaurant for a leisurely lunch of traditional Portuguese cuisine, followed by another wine tasting.

Then it's time to hop aboard a riverboat for an hour-long cruise down the tranquil Douro River. Relax and admire the beautiful scenery of the valley and the rolling hills along the riverbanks.  

After the cruise, your guide will return you to Porto, where you can spend the evening at leisure in the city's lively Ribeira area.

Day 8: Explore Porto & Northern Portugal

The Sanctuary of Bom Jesus do Monte in Braga

With the whole day free, you can get lost in more of Porto's charms, or hit the road and explore some nearby day trip ideas:

  • Braga: Immersed in historical and spiritual surroundings, Braga is an old city with young energy. Within the café-filled center, students from the nearby university meet to socialize and discuss ideas, while a short distance away tourists will enjoy seeing the famous Bom Jesus do Monte (Bom Jesus Sanctuary) and the oldest cathedral in the country.

  • Aveiro: Travelers don’t need to visit Italy to experience romantic gondola rides—just head to Aveiro, known as the "Venice of Portugal." This small coastal city is famous for its quaint canal system, colorfully painted boats, and vibrant buildings. At just under an hour's drive from Porto, it makes for an easy and immersive day trip.

  • Guimarães: History buffs shouldn’t leave northern Portugal without seeing where the country’s origins began. Home of Portugal’s first king, Guimarães Castle was home to the royal family, but there are plenty more medieval structures where that came from. Between the historic streets, churches, and natural landmarks, visitors will feel like they've stepped back in time.

  • Viana do Castelo: Drive an hour up the coast to reach this visually appealing beach town, home to both a medieval center and beautiful beaches. Visit the Templo-Monumento de Santa Luzia (Santa Luzia Temple), which is the city’s most popular landmark. As a fishing port, it’s also an excellent location for devouring seafood.

  • Peneda-Gerês National Park: Do you love nature, hiking, and stumbling across long-lost medieval remnants? If yes, a trek through Portugal’s only national park is a must. Located in the districts of Viana do Castelo and Braga, it’s an easy place to incorporate within an itinerary. 

  • Vigo: One of the cooler things that comes with a visit to northern Portugal is its proximity to Spain. Vigo is a seaside city rich in culture and with plenty to do but is often overlooked. Historically, it was a major departure point for early navigators, and today these maritime roots still hold strong. Vigo is considered one of the larger fishing ports in the world, and as such is a great place to indulge in fish and seafood.

Day 9: Drive to Évora, Afternoon Tour


This morning, after breakfast at your hotel, you'll get back on the road and head to the town of Évora—a driving distance of about three hours. 

After lunch in town, begin a private guided tour to discover the most impressive treasures of this UNESCO-listed city. Your guide will cover Évora's main monuments, including those dating to the golden age of Portuguese maritime discoveries, while answering questions along the way. This tour is especially ideal for visitors wishing to get an overview of the city's major events, which have always been linked to the most significant moments of Portugal's history. 

In the evening, you'll have the free time to explore Évora's streets and dining scene on your own.

Day 10: Explore Évora & the Alentejo

Vineyards in the Alentejo

Spend today exploring more of Évora on your own, or head out into the surrounding Alentejo region, where the pace of life slows amid the area's iconic golden plains. This sparsely populated yet vast swath of land between the Algarve and Lisbon offers scenic rolling hills, olive groves, vineyards, and charming fortified towns with a number of walking trails, Neolithic monuments, rustic wineries, and cork production facilities. 

Day 11: Drive to Lagos 

Lagos is famed for its sandy beaches

 After breakfast, check out of your hotel in Évora and hit the road towards Lagos, a seafaring town on the western side of the Algarve region, situated along Portugal's southern coast. 

Upon arrival, you'll check in to your hotel and have the rest of the day to explore on your own. Lagos is known for its charming inner-walled old town, pretty harbor, dramatic sandstone cliffs, and beautiful beaches, as well as authentic restaurants and buzzing nightlife. Locals are proud to say that Lagos has not succumbed to mass tourism like other cities in the Algarve, retaining its distinctive character and laid-back charm. 

Days 12 & 13: Explore Lagos & the Algarve

Take the wooden walkway to scenic Praia do Camilo in Lagos

The next two days are yours to discover the incredibly scenic area in and around Lagos, its nearby beaches, and the larger Algarve region.

If you haven't spent much time in the port city of Lagos yet, take some time to wander through its 16th-century inner walls for cobblestoned streets and inviting squares. You'll also find a great range of restaurants and nightlife options both inside and outside the walls.

If beaches are high on the list, you'll find several dreamy options to choose from, offering a variety of services, watersports, and boat excursions. For example, there's Pinhao Beach, a peaceful cove known for its secluded, picturesque setting. Another option is the Ponta da Piedade, which offers more dramatic sandstone cliffs and bright turquoise water (a range of boat tours depart from here). Meanwhile, Praia do Camilo enjoys a memorable view from the top while 200 wooden steps lead to a sheltered sandy cove. 

The scenery doesn't stop there: the surrounding Algarve region offers plenty to see and do within its pristine natural parks, bustling resort towns, and authentic white-washed villages.

Day 14: Drive to Lisbon & Departure

Sunset over Lisbon's Abril Bridge

After breakfast, it's time to bid the beach farewell and start the four-hour drive back to Lisbon's airport to return your rental car and catch your departing flight. Safe travels!

More Portugal Itineraries

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

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