This itinerary includes Portugal's two biggest cities, a slew of historic villages, and some spectacular beaches for an epic adventure to remember. Start off in up-and-coming Lisbon to explore ancient ruins and trendy districts before making your way north to UNESCO-listed Porto (and its nearby wine region). You'll also get time in the university towns of Évora and Coimbra—each with their own medieval attractions and dining scenes—before kicking back for a few days in the Algarve.


  • Take an evening gastronomy tour around Lisbon on your first night
  • Explore the fairytale village of Sintra including its 16th-century monastery
  • Stay two nights in Portugal's charming medieval capital en route to Porto
  • Drive through the Alentejo region to get to the inner-walled city of Évora
  • Spend your last few days relaxing on gorgeous sandy beaches near Lagos

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon - Culinary Excursion Lisbon
Day 2 Half-Day Tour of Lisbon Lisbon
Day 3 Day-Trip to Sintra, Cascais & Estoril Lisbon
Day 4 Drive to Coimbra, via Óbidos & Alcobaça Coimbra
Day 5 Guided Tour of Coimbra Coimbra
Day 6 Transfer from Coimbra to Porto - City Tour Porto
Day 7 Day-Trip to Guimarães Porto
Day 8 Day-Trip to Douro Valley Porto
Day 9 Transfer to Évora, via Tomar Évora
Day 10 Explore Évora & the Alentejo Region Évora
Day 11 Return to Lisbon - Transfer to Lagos by Train Lagos
Day 12 Explore Lagos & the Algarve Region Lagos
Day 13 Transfer to Lisbon by Train Lisbon
Day 14 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Lisbon - Culinary Excursion

Welcome to Lisbon!
Welcome to Lisbon!

Welcome to Portugal! Upon arrival at Lisbon's airport, you will be met by a driver who will transfer you to your hotel. Take some time to rest before you start exploring. 

When evening hits, you'll take part in a gourmet food tour in Lisbon—a great way to experience the city for the first time! Wear a good pair of walking shoes because you, along with your English-speaking guide, will meander through a series of authentic winding alleys tasting the incredible flavors of Portuguese gastronomy, especially in the neighborhood of Campo de Ourique—practically a city within the city—that sets the food culture and gastronomic trends of Lisbon.

Over the course of four hours, you will visit seven spots that brilliantly link tradition with modernity. Experience ways that locals have reinvented restaurant concepts, including a market and hotel school while getting a taste of culinary recipes that have become world-famous.

Day 2: Half-Day Tour of Lisbon

Statue at Praca do Comercio
Statue at Praca do Comercio

Today you'll get to discover Lisbon on a half-day tour visiting key sites and some well-kept secrets, exposing the city's unique atmosphere and authenticity. This will be a fun adventure as you travel around the city utilizing the yellow tram system broken up with relaxed strolls. Make sure to wear a good pair of walking shoes. 

The tour includes the following:

  • Praça do Comércio: the largest of Lisbon’s plazas
  • Baixa: the 'new city', built after the devastating  1755 earthquake
  • Praça da Figueira: Lisbon’s traditional market square
  • Rossio: the heart of downtown Lisbon
  • Iron Lift Viewpoint: a stellar 360º view over the downtown district
  • Largo do Carmo: the setting for the democratic revolution of 1974
  • Carmo ruins: the only Gothic monument of the city
  • St. Roque Church: a Baroque extravaganza
  • Bairro Alto: the lively bohemian district
  • Chiado: the city's most elegant shopping area
  • Portas do Sol: a breathtaking view over Alfama (the Old Town)

In the evening, you'll dine at one of the best Fado restaurants in Lisbon for traditional Portuguese cuisine interspersed with authentic singing and music.

Day 3: Day-Trip to Sintra, Cascais & Estoril

Sintra's fairytale setting near Lisbon
Sintra's fairytale setting near Lisbon

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 the 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: Drive to Coimbra, via Óbidos & Alcobaça

Make a stop in historic Óbidos
Make a stop in historic Óbidos

Today you will make the two-hour drive to Coimbra, Portugal's medieval capital, with a beautifully-preserved old town and historic university. Along the way, you will make a few stops starting with adorable Óbidos.

Surrounded by a classic crenelated wall, Óbidos’ gorgeous historic center is a labyrinth of cobblestoned streets and flower-bedecked, whitewashed houses livened up with dashes of vivid yellow and blue paint. You will have time to take a self-guided visit around this historic village with its stunning castle, which dates back to almost a thousand years. 

After a morning in Óbidos and a traditional Portuguese lunch (if you so choose), the journey continues north. Your next stop is Alcobaça, a town with a charming center with a little river and bijou bridges, as well as the magnificent 12th-century Mosteiro de Santa Maria de Alcobaça—one of Portugal’s most important UNESCO World Heritage Sites. 
From here, continue the drive to Coimbra where you'll have the evening to relax and wander the streets.

Day 5: Guided Tour of Coimbra

Coimbre's historic core
Coimbre's historic core

After breakfast at your hotel, it's time for a guided tour of Coimbra.

This is the medieval capital of Portugal and the site of the country’s greatest university: the University of Coimbra, established in 1290. The city wears its weighty importance in Portuguese history with dignity and pride, witnessed by its multicolored collage of buildings that span nearly a millennium. Observe how Coimbre's historic core cascades down a hillside creating a lovely setting along the east bank of the Rio Mondego.

Once you've experienced the city with your guide, you'll have the rest of the day to continue exploring on your own.

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Day 6: Transfer from Coimbra to Porto - City Tour

Depart Coimbre and head north to Porto
Depart Coimbre and head north to Porto

This morning you'll be picked up from your hotel in Coimbra for a transfer to Portugal's second-largest city of Porto, a drive that takes about an hour and a half.  

Once you arrive, it's time for a city excursion. 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 StationClerigos TowerChurch of St. FrancisLello BookshopSta. Catarina StreetMajestic Café, and Bolhão Market, to name a few.

After visiting the imposing Porto Cathedral with its superb silver altarpiece, you head to the banks of the immense Douro River with views of Ribeira Plaza and the D. Luís Bridge. Finish the excursion with a visit to one of the famous port houses before heading back to your hotel.

Take the rest of the evening to explore Porto's dining scene on your own (or ask your guide for suggestions before parting ways!)

Day 7: Day-Trip to Guimarães

Dukes of Bragança Palace
Dukes of Bragança Palace

After breakfast in Porto, you'll head out for a day-trip to Guimarães, about an hour by car, northwest of the city.

This is a significant place of Portuguese history as it is where the country originated. You'll definitely want to head to the 10th-century Guimarães Castle—located on a hilltop with sweeping views—where the first royal family lived. There's also the 14th-century Dukes of Bragança Palace, built in the style of a French chateau, with a museum showcasing furniture, tapestries, and weapons. Beyond that, there are many more medieval buildings to explore by foot, as well as charming streets, cafes, churches, and natural landmarks.

Following the visit, return to Porto and enjoy the evening on your own.

Day 8: Day-Trip to Douro Valley

Douro Valley
Douro Valley

After breakfast in Porto, you will be picked up at your hotel for a full-day excursion in the Douro Valley, one of the most beautiful wine regions in the world!

To kick it off, you can learn about the production process of Port wine at one of the most notable vineyards in the Douro Valley, while partaking in several Port wine tastings. If you are not particularly fond of Port wine, you can alternatively visit a table wine vineyard and producer. The tour also includes a visit to a local olive oil producer since this is one of the most beloved products of the region. 

In the mid-day, you'll have lunch at a traditional Portuguese restaurant where there will be more time to learn about the area and ask your guide questions. Next, is a relaxing and scenic boat trip along the valley with photo ops at several magnificent viewpoints along the Douro River.

Following the boat trip, you'll return to Porto in time for dinner on your own.

Day 9: Transfer to Évora, via Tomar

Tomar's picturesque setting
Tomar's picturesque setting

Today you'll make your way to the charming and historic city of Évora by way of a private transfer. 

Along the journey, your driver will stop in the city of Tomar to visit the Convento de Cristo, which forms a beautiful backdrop from almost any vantage point. Eight-and-a-half centuries after its founding, this venerable headquarters of the legendary Knights Templar is a rambling concoction of Gothic, Manueline and Renaissance architecture that bears extravagant witness to its integral role in centuries of Portuguese history. You will need at least 1.5 to 2 hours to visit the monastery (self-guided).

After departing Tomar, it's time for one more stop at Almourol Castle, a fortress located on the top of a small rocky island in the middle of the Tagus River. Despite its nearly 2,000-year-old age, the castle is well-kept and has long controlled the waterway along the Tagus. It is widely accepted that the name comes from the Arabic word almorolan, which means ‘high rock’, and, indeed, this definition perfectly describes the wonderful location of the castle. Take some time to explore (self-guided) before getting back on the road.   

From here, you will then continue the drive to Évora. Once you've checked into the hotel, take an evening walk through the cobbled streets and get a taste of the city's architecture and dining options.

Day 10: Explore Évora & the Alentejo Region

Vineyard in Alentejo
Vineyard in Alentejo

After breakfast at your hotel, you'll have the entire day to explore more of Évora at your own pace—a small city blessed with a large number of national monuments inside its ancient Moorish walls.

Alternatively, you could get in a car and drive around the surrounding Alentejo region, Portugal's biggest, which covers about 30% of the country. The sparsely populated yet vast swath of land between the Algarve region 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.

No matter how you spend your day, enjoy the slow pace of life; residents in the Alentejo region are more traditional than other parts of Portugal, reflected in their homecooked cuisine and local handicrafts.

Day 11: Return to Lisbon - Transfer to Lagos by Train

Lagos is known for stunning beaches
Lagos is known for stunning beaches

This morning, you'll return to Lisbon and then take the train trip to Lagos (about 5 hours). This is a town on the western end of the Algarve Region, situated along Portugal's picturesque southern coast. 

Once you've arrived at Lagos Railway Station, you'll make your way to the hotel for check-in and then 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, 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, and the city still retains its distinctive character and laid-back charm. 

The best way to start is by walking around!

Day 12: Explore Lagos & the Algarve Region

Take the wooden walkway to scenic Praia do Camilo in Lagos
Take the wooden walkway to scenic Praia do Camilo in Lagos

You'll have the entire day to explore the incredibly scenic area in and around Lagos, its nearby beaches, and the larger Algarve Region any way you'd like.

If you haven't spent much time in the port city of Lagos yet, it's definitely worth 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 (not surprisingly, outside is more modern).

If beaches are high on the list, you'll find a number of dreamy options to choose from offering a variety of services, watersports, and boat excursions. For example, there's Pinhão 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: If you have a car, the surrounding Algarve region offers plenty to see and do within its pristine natural parks, bustling resort towns, and authentic white-washed villages.

Day 13: Transfer to Lisbon by Train

Portugal's scenic capital
Portugal's scenic capital

This morning, you'll make your way to the railway station for the train to Lisbon. Upon arrival, check into your hotel and take the remainder of the day to rest and enjoy the city. 

If you're returning to Lisbon and haven't had a chance to fully explore the districts on your own yet, a good place to start is charismatic Alfama 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 look for and taste the delicious Pastel de Belém, a traditional pastry found here. 

Another great neighborhood is the bohemian style Bairro Alto where you can ride the Bica Funicular, visit the São Roque Church, and take in the views from Miradouro de São Pedro de Alcântara. Many of the neighborhood's centuries-old houses are decorated with colorful street art. 

Day 14: Depart Lisbon

Goodbye, Lisbon!

It's time to say goodbye to Portugal! Depending on the time of your flight, squeeze in one more walk through the streets of Lisbon, perhaps picking up some last-minute souvenirs. At the designated time you will be picked up at your hotel and transferred to the airport for your departure onwards. Safe travels!


Map of Ultimate Portugal Tour: Lisbon, Porto, The Algarve, Douro Valley, & More - 14 Days
Map of Ultimate Portugal Tour: Lisbon, Porto, The Algarve, Douro Valley, & More - 14 Days