Check off the highlights of the Iberian Peninsula on this two-week jaunt around Portugal and Spain. It begins in Lisbon, where you'll see centuries of history written in its cobbled streets on city tours and cultural outings. After a trip to Sintra's mountaintop palace, you'll head north to romantic Porto for wine tastings before jetting off to Spain to enjoy the fruits of Madrid and Barcelona.


  • Experience the history, music, and culture of Lisbon
  • Tour the mountaintop palaces of Sintra
  • Enjoy port wine tastings in the river city of Porto
  • Go on food tours of Madrid and see the Spanish capital's sights
  • Take a tapas tour and laze on the beaches of Barcelona

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon (Portugal), Optional Activities Lisbon
Day 2 Guided City Tour, Dinner & Fado Performance Lisbon
Day 3 Day Trip to Sintra, Belém Tuk-Tuk Tour Lisbon
Day 4 Transfer to Porto, Stop in Óbidos & Nazaré Porto
Day 5 Porto City Tour, Wine Tasting Porto
Day 6 Day Trip to Douro Valley, Winery & Boat Tour Porto
Day 7 Fly to Madrid (Spain), Optional Activities Madrid
Day 8 Madrid Tapas & History Tour Madrid
Day 9 Free Day in Madrid Madrid
Day 10 Train to Barcelona, Optional Activities Barcelona
Day 11 Barcelona Wine & Tapas Tour Barcelona
Day 12 Beach Day in Barcelona Barcelona
Day 13 Free Day in Barcelona Barcelona
Day 14 Depart Barcelona  

Detailed Itinerary

Day 1: Arrive in Lisbon (Portugal), Optional Activities

One of the most fun ways to get around Lisbon is via its famous tramway

Welcome to Portugal! This sliver of a country on the Iberian Peninsula may be small, but it boasts one of the longest empires in European history, spanning from 1415 to the transfer of Macau back to China in 1999. This two-week adventure kicks off in the nation's capital of Lisbon, located at the mouth of the Tagus River. This city is said to be four centuries older even than Rome (the Phoenicians first settled in Lisbon around 1200 BCE). That historical legacy is written on every corner of this medieval metropolis, from Lisbon's forts to its castles, monasteries, plazas, and more.

You'll arrive at the airport, and a driver will be waiting to transfer you to your hotel in the historic center. Then you'll have the rest of the day to explore the capital's famous seven hills. Lisbon's downtown district is a kinetic mix of tourists and locals meandering around its plazas and amid its traditional shops. The waterfront neighborhoods are dotted with grand plazas and pastel-colored buildings dating back hundreds of years. If you like, hop on the tramway, Lisbon's network of old cable cars that rumble up and down the hills—there's no better way to explore the city.

Day 2: Guided City Tour, Dinner & Fado Performance

Head up into the hills and discover the highlights of Lisbon

This morning, you'll get to know Lisbon by hopping from neighborhood to neighborhood on a city tour. Leading this three-hour excursion is an expert local guide who will point out the major sights of Central Lisbon and recount anecdotes about local history. It's a great introduction to the culture of this fascinating city.

The tour includes stops at many highlights, including the upscale shopping area around Chiado Square and the Lisbon Cathedral, which dates to the 12th century and is the oldest church in the city. You'll also visit Baixa, located in the city's waterfront downtown area. Its central square, Rossio, has been one of Portugal's main plazas since the Middle Ages. You'll feel like you've stepped back in time while strolling beautiful Alfama, an ancient Moorish neighborhood.

After the tour, you'll return to the hotel and have some free time. Later, head out for dinner and a show. You'll sit down to eat at a traditional fado restaurant, where great cuisine and great music come together. Fado is a distinctly Portuguese style of music, born in Lisbon in the early 19th century. Not unlike the tango, this music is defined by its mournful strings and melancholic verses speaking of passion, struggle, romance, and unrequited love. You can't find a better dinner show in the city.

Day 3: Day Trip to Sintra, Belém Tuk-Tuk Tour

Sintra's hilltop setting near Lisbon
Visit the palace in the clouds at Sintra's mountaintop Pena Palace

After breakfast, your driver will pick you up for the ride outside the city to your first stop on a day tour: Sintra. Located half an hour east of Lisbon, this resort town in the Sintra Mountains is known for its forested hills, upscale villas, and Moorish palaces. Start with a visit to the Palacio Nacional da Pena (Pena Palace). This 19th-century romanticist castle mixes Moorish and Portuguese late-Gothic architectural styles with distinct features like gargoyles, ornate battlements, and colorful terraces. 

At the end of the palace visit, you'll return to Lisbon and embark on the second leg of today's tour. No more walking, as you'll kick back in a tuk-tuk (auto rickshaw) as your driver zips you around Belém. This lovely riverfront area is a bastion of history in the form of monuments, ancient fortresses, and palaces, all of which conjure the heyday of Lisbon's maritime past. Highlights include the 16th-century Torre De Belém and the awe-inspiring Jerónimos Monastery. Afterward, you'll return to your hotel.

Day 4: Transfer to Porto, Stop in Óbidos & Nazaré

The Castle of Óbidos and its surrounding medieval walled town

In the morning, you'll leave Lisbon with your driver and head north to the historic city of Porto. The journey takes about three hours, but you'll stop on the way at heritage sites. About halfway through the drive, you'll arrive in the medieval walled town of Óbidos. Located on high ground near the Atlantic coast, Óbidos' historic center is a labyrinth of narrow cobblestone streets lined with whitewashed houses spackled with yellow and blue paint. Explore the narrow streets and impressive 14th-century castle. Afterward, you can browse the handicraft and souvenir shops.

Then head about 30 minutes north to the coast and the fishing village of Nazaré, where you'll stop for a delicious seafood lunch. You'll have a bit of time afterward to explore the surrounding areas. The coast is the star here, as its epic surf is a prime destination for big-wave riders from around the world. 

Continue on to Porto and check into your hotel. Then, take the rest of the day to enjoy this 2,000-year-old city. One of the best places to begin is the medieval Ribeira district, whose narrow and cobblestoned streets wind past merchants' houses and cafés along the Douro River. It includes landmarks like the São Francisco Church, known for its lavish Baroque interior and ornate gilded carvings. In the evening, sample some of the staples of Porto's culinary scene: fresh seafood, local organic produce, wines produced in the Douro Valley, and of course, a glass of port.

Day 5: Porto City Tour, Wine Tasting

Porto Overview
Tour the colorful riverfront city of Porto

Your day begins with a three-hour tour of Porto. There's much history in this UNESCO World Heritage city, as it has been the site of Celtic, Roman, and Moorish occupation, an invasion by Napolean and Spanish troops, and even a civil war. Learn all about it as you tour Porto's historic center, which includes a stop at the Praça da Liberdade (Liberty Square), the city's largest and most impressive plaza. You'll also visit Rua Santa Catarina (the main shopping thoroughfare), Gomes Teixeira Square, and the Baroque Igreja dos Clérigos church, which dates to 1750.

From there, head to the iconic São Bento Railway Station (built in 1900 on the site of a former convent) and the riverfront Ribeira neighborhood, which is the heart of Porto's nightlife scene. You'll also learn the history of Porto's emblematic Dom Luís I Bridge, a double-decked iron arched bridge that stands 279 feet (85 m) over the Douro River. On this waterway, colorful wooden rabelo boats line up in front of the old port wine cellars.

Plan your trip to Spain
Chat with a local specialist who can help organize your trip.
Speaking of which, after the tour, you'll head to one of these cellars to taste world-famous port wine. During this one-hour experience, a local guide will lead you through the wine's history as you sample various tawny and ruby ports in the tasting room. Afterward, you'll return to your hotel.

Day 6: Day Trip to Douro Valley, Winery & Boat Tour

See the highlights of Portugal's most famous wine region, the Douro Valley

Your driver will pick you up in Porto this morning for the 1.5-hour trip outside the city to the Douro Valley, a fertile grape-growing region that produces some of Portugal's best wines. This full-day tour includes a visit to a quinta (winery estate). Here, you'll tour the vineyards, production facilities, and wine cellar and enjoy a tasting.

Afterward, you'll drive to a nearby town where your guide will recommend the perfect restaurant for a lunch of traditional Portuguese cuisine. Then hop aboard a riverboat for an hour-long cruise down the tranquil Douro River. Relax and admire the beautiful scenery of this valley, which includes vineyard-covered hills and centuries-old estates. The Douro Valley is so lovely it's even been declared a UNESCO World Heritage Site. Afterward, you'll return to Porto and your hotel.

Day 7: Fly to Madrid (Spain), Optional Activities

El Prado opened in 1819 and is Madrid's national art museum

It's time to say goodbye to Portugal! After breakfast, you'll transfer to the airport for the one-hour flight from Porto to Madrid. On arrival at the airport, you'll be greeted by your driver, who will transfer you to your hotel in the city center. Take some time to settle in before heading out to explore this marvel of a city.

Madrid exudes culture and fun. It boasts over 80 museums and thousands of historical monuments and landmarks. One can't-miss museum is El Prado. It features one of the world's finest collections of European art, including works by Velázquez, El Greco, and Goya. For a deeper dive, there's also El Paseo del Arte, an art walk that, besides El Prado, includes stops at the Reina Sofía National Museum and the Thyssen-Bornemisza Museum.

When night falls, indulge in Madrid's world-class culinary scene. If you want to dine amid history, head to Botín in the city center. No less than Ernest Hemingway described it in his seminal novel "The Sun Also Rises" as the best restaurant on earth. And when the hour gets late, feel free to revel in the city's nightlife scene. Some of the best areas for bars and clubs include Huertas and Chueca.

Day 8: Madrid Tapas & History Tour

Enjoy the authentic tapas taverns
In Spain, tapas are as much about the company as the food

In the afternoon, you'll get a tasty lesson in the history of Spain on a walking tour of the historic center. During this three-hour excursion, your local guide will lead you to four taverns/bars emblematic of Madrid's tapas (small plates) scene. You'll quickly learn that tapas bars are an integral part of the social fabric in Spain—places where friends, family, and colleagues get together to socialize over a few plates and cañas (glasses) of beer or wine.

The tour includes tastings of 16 classic tapas paired with Spanish wines. Cap the experience by enjoying the best churros y chocolate in the city. Afterward, you'll return to your hotel.

Day 9: Free Day in Madrid

Madrid - Plaza Mayor
Go sightseeing and visit highlights like the Plaza Mayor
Today is yours to spend however you like. You can go shopping and take in a show at glitzy Gran Vía, Madrid's answer to Broadway. Here, you'll find plenty of theaters showing plays and musical productions, many of which are geared toward the whole family. Needless to say, the options for culture in this city are vast, and you could also visit museums, art galleries, and live music venues if the mood strikes.

Day 10: Train to Barcelona, Optional Activities

Barcelona's Arc de Triomf
The Arc de Triomf, one of the highlight landmarks of Barcelona

In the morning, you'll transfer to the train station in Madrid for the three-hour ride to Barcelona. Welcome to the Mediterranean coast and the beautiful capital of Catalonia! Upon arrival at the station, you'll transfer to your hotel in the historic Old City. After settling in, you'll want to head back out and experience Barcelona's culture and energy first-hand.

You might consider visiting Mount Montjuïc. This famous hill stands 1,988 feet (606 m) high and overlooks the Port of Barcelona. A cable car takes you up to the 17th-century Castle Montjuïc and offers panoramic city views. The Poble Espanyol is also fun to visit. Constructed in 1929, this open-air museum features over 100 recreated buildings in the style of traditional Spanish villages.

And when the sun goes down over the city, make sure you're near the Magic Fountain of Montjuïc, which is named for the dazzling display of water and colored lights that occur after dark. It's the best free show in the city, one whose effect is heightened by the hundreds of spectators and a communal atmosphere.

Day 11: Barcelona Wine & Tapas Tour

Sample a variety of tapas in Barcelona
Sample a variety of tapas and drinks in Barcelona

As mentioned earlier, tapas are a cultural touchstone found in every corner of Spain—and Barcelona is no exception. After a day exploring the city on your own, head out on a four-hour evening wine and tapas tour. During the jaunt, your local guide will take you around Eixample, an upscale residential district that also boasts a thriving nightlife and restaurant scene.

Throughout the tour, you'll stop in at various tapas bars, restaurants, and bodegas (small bars/wine cellars) to enjoy hot and cold appetizers paired with local wine and beer. The types of places you'll visit range from atmospheric local bars to organic eateries to cutting-edge gourmet restaurants. Afterward, you'll return to your hotel.

Day 12: Beach Day in Barcelona

Self-Guided Beach Day in Barcelona
Spend a free day enjoying the golden sands in Barcelona
As locals will attest, one of the best ways to spend a day in Barcelona is at the beach. The sun-kissed golden sands on the coastline here are wide, inviting, and open to the public. So this morning, you'll head to one of Barcelona's fine municipal beaches. Here, you can sunbathe, jog, or cycle along the promenade—followed by a refreshing dip in the water. You also paddle along the coast in a kayak, on a standup paddleboard, or take it easy on a sunset cruise. It's also always an option to head north to Costa Brava, a region known for its idyllic beaches and which makes for a great day trip from Barcelona.

Day 13: Free Day in Barcelona

Visit masterworks by architect Antoni Gaudí, like Sagrada Família

It's another free day to go sightseeing on your own. If you haven't already, you can visit Gaudí architectural landmarks like Park Güell, Casa Milá, and the jewel in the crown, La Sagrada Família. This iconic Roman Catholic basilica is an impressive mix of Gothic, Catalan-modernism, and Art Nouveau architectural styles. Despite construction on the church beginning in 1882, it's still technically under construction and was only consecrated in 2010.

Other landmarks you can visit include the open-air architectural museum of Poble Espanyol and Las Ramblas, the pedestrian thoroughfare running through the heart of Barcelona's medieval Gothic Quarter. At the end of the day, enjoy some more great tapas and drinks before returning to your hotel.

Day 14: Depart Barcelona

Sunset over Park Güell in Barcelona
Alas, you've reached the end of the line on this Iberian adventure. At the appropriate time, a driver will pick you up at your hotel in Barcelona and transfer you to the airport where you'll catch your flight home. Adiós!

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Map of Ultimate Portugal & Spain: Lisbon, Porto, Madrid & Barcelona - 14 Days
Map of Ultimate Portugal & Spain: Lisbon, Porto, Madrid & Barcelona - 14 Days