Combine historic cities with off-the-beaten-path treasures on this 10-day, self-drive journey through Portugal and Spain. Start by enjoying the food and historical landmarks of Porto, then drive to the León region of Spain to marvel at the ancient sandstone buildings in Salamanca. Take a hot-air balloon over the countryside of Ávila, hike through the pine forests of Sierra de Guadarrama National Park, tour the medieval walls of Segovia, and finish the trip exploring the parks, plazas, and markets of Madrid.


  • Join locally-led food and city tours in Porto
  • See the remarkable sandstone architecture of Salamanca
  • Ride a hot-air balloon over the hills of Ávila
  • Hike in national parks and go wine tasting in Segovia
  • Enjoy tours of Madrid's markets and neighborhoods 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Porto (Portugal), Foodie Tour Porto
Day 2 Guided Porto City Tour Porto
Day 3 Pick Up Rental Car & Drive to Salamanca (Spain), Optional Stops Salamanca
Day 4 Guided Salamanca City Tour Salamanca
Day 5 Drive to Ávila, Guided City Tour Ávila
Day 6 Ávila Hot-Air Balloon Ride, Sweets Workshop Ávila
Day 7 Drive to Segovia, Guided City Tour Segovia
Day 8 Hike Sierra de Guadarrama, Wine Tasting Segovia
Day 9 Drive to Madrid, Optional Activities Madrid
Day 10 Depart Madrid  

Detailed Itinerary

Day 1: Arrive in Porto (Portugal), Foodie Tour

Visit the best restaurants in downtown Porto on today's food tour

Welcome to Portugal! This small country at the edge of the Iberian Peninsula is the oldest nation in Europe, having officially been founded in 1143. You'll arrive in Porto, a historic and romantic city on the Douro River that's 20 years older than the country it occupies (Porto was founded in 1123). Upon arrival at the airport, a driver will pick you up and transfer you to your hotel in the city center.

After checking into your hotel and dropping off your bags, you'll meet a local guide for a tasty half-day food tour around Porto's historic downtown. This small-group excursion focuses on the city's culinary renaissance. It includes stops at family-run eateries, cafés, and food purveyors focusing on simple ingredients and recipes passed down over generations. In the evening, you'll get to sample another staple of the region: port wine. You'll taste three different versions, including one vintage, as you learn about the history of this timeless drink.

Day 2: Guided Porto City Tour

Walk in the footsteps of Porto's rich history on a guided city tour

In the morning, you'll meet a local guide and embark on a three-hour tour of Porto. During this excursion, you'll visit historic enclaves, trendy areas, and cultural hubs as your guide reveals the city's rich history, which includes tales of ancient heroes, battles, and civil wars. You'll also learn how Porto earned its famous nickname "Invicta" (the Invincible City), which derives from a time in the 19th century when Porto beat back an enemy after surviving a year-long siege.

Highlights of the tour include a walk down Boavista (the longest avenue in Porto) and a visit to Foz, an affluent seaside district that boasts fine museums, monuments, and public gardens. Next, you'll head to Porto's historic center—a UNESCO World Heritage Site—to admire architectural landmarks that run the gamut from Romanesque, Gothic, Baroque, and neoclassical. These include the São Bento Railway Station (built in 1900 on the site of a former convent), Clerigos Tower, the Church of St Francis, Rua Santa Catarina, and Bolhão Market, to name a few.

After visiting the 18th-century Porto Cathedral, with its superb silver altarpiece, you'll finish the tour along the banks of the Douro River with views of Ribeira Plaza. On your own, you can continue exploring Porto's Ribeira neighborhood, which overlooks the river. Famed for its colorful waterfront houses, this historic enclave offers a true taste of authentic Porto. Have fun getting lost on the winding streets leading up from the river.

Day 3: Pick Up Rental Car & Drive to Salamanca (Spain), Optional Stops

Stop at historic landmarks on the way to Salamanca, like Guarda's Cathedral

After an early breakfast, it's time to pick up your rental car and hit the road on a 3.5-hour drive east over the mountains into the Castile and León region of Spain on your way to Salamanca. It's a direct 218-mile (350 km) drive, but you'll have plenty of options to visit some lovely off-the-beaten-path places in Portugal along the way. 

One option just east of Porto is Viseu, a city famous for its local wines from the famous Dão grape-growing region. Located in the coastal mountains, Viseu boasts a stunning 12th-century cathedral that's a mix of architectural styles, including Roman Gothic and Baroque. Since 2015, the city has hosted a street-art festival celebrating Portuguese and international artists.

Another option is Guarda. Nestled in the Serra da Estrela mountains at 3,465 feet (1,056 m), this is the highest-altitude city in Portugal. During the Middle Ages, Guarda was a vital stronghold in defense of the border against Spain. Another good detour is to Cuidad Rodrigo, which boasts lovely plazas, streets lined with Renaissance mansions, a castle, and splendid 12th-17th-century walls. Eventually, you'll cross the border into Spain and arrive in Salamanca, where you'll check into your hotel. 

Day 4: Guided Salamanca City Tour

Tour the historic center of Salamanca

Eat a hearty breakfast because this morning you’ll head out for a discovery tour of Salamanca's ancient sandstone buildings and highlight attractions. During this 2.5-hour guided tour, you'll visit awe-inspiring medieval landmarks like the 18th-century Plaza Mayor, City Hall, cathedrals, and Renaissance palaces. You'll also visit the House of Shells, a restored 15th-century house decorated with hundreds of fake scallop shells. 

Interestingly, Salamanca comes most alive at night. This is when the city's thousands of university students take to the streets to socialize and revel. When the sun goes down, you should definitely head to the Plaza Mayor, which is luminous and dazzling when awash in light effects. After dinner in the city center, you can retire to your hotel.

Plan your trip to Spain
Chat with a local specialist who can help organize your trip.

Day 5: Drive to Ávila, Guided City Tour

The cathedral of Ávila
See the sights in Ávila, like the Romanesque/Gothic Cathedral

Hop in the car this morning for the easy one-hour drive southeast to Ávila, the capital of the province of the same name. After checking into your hotel, head to the Ávila Cathedral, where you'll meet your guide and embark on a 2.5-hour tour of the historic center. There's a lot to marvel at here, as Ávila's medieval center is remarkably well-preserved, so much so that it was declared a UNESCO World Heritage Site in 1985.

You'll visit the highlight landmarks and areas within Ávila's old city walls. These include the Plaza Mercado Chico (main square), the Jewish and Muslim quarters, and the 12th-century Cathedral, considered the first Gothic cathedral in Spain. After the tour, you'll have the rest of the day to enjoy Ávila on your own.

Day 6: Ávila Hot-Air Balloon Ride, Sweets Workshop

Enjoy a morning hot-air balloon ride over Ávila

You've seen Ávila from the ground, now it's time to see it from the air. Wake up before dawn and transfer to a take-off site where you'll witness the inflation of a hot-air balloon. When ready, hop in the basket and gently rise into the air as the sun rises above the horizon and illuminates the city. During the hour-long flight, you'll enjoy birds-eye views of Ávila's highlights, like the historic center, the Cathedral, ancient city walls, and the surrounding Sierra de Gredos mountains. After the flight, you'll return to the landing site and toast your balloon ride with a glass of bubbly Spanish cava. 

Spend the rest of the day on terra firma as you enjoy a private lesson where you'll learn to make the famous yemas de Santa Teresa (candied egg yolks). These delectable tidbits are a staple of Ávila dating back to the year 1860, and the class takes place in a traditional workshop in the heart of the city. Led by a local pastry chef, you'll spend an hour learning the technique of making these tasty treats by hand from recipes passed down over the generations. Of course, at the end of the workshop, you'll enjoy the yolk sweets you've created.

Day 7: Drive to Segovia, Guided City Tour

Visit Segovia's Roman Aqueduct, one of the most impressive landmarks in Spain

It's time to get back on the road today for the one-hour drive northeast to Segovia. This is one of the most well-preserved historic cities in the country, with no shortage of ancient history. Segovia is perhaps most famous for its Roman Aqueduct and medieval Old Town, both UNESCO World Heritage Sites. After checking into your hotel, you'll head out on a guided tour to see these and other historic landmarks.

The tour begins at the iconic Roman Aqueduct, which is the pride of the city. It runs 8 miles (14 km), stands an impressive 93 feet (28 m), and features two tiers comprised of 160 arches. Considering this aqueduct was built nearly 2,000 years ago, it remains in remarkably good condition. 

Next, you'll visit Old Town, situated on a bluff overlooking the Eresma and Clamores rivers. For centuries, Moors, Christians, and Jews coexisted in harmony here, and this is seen in the unique buildings with architectural influences that run the gamut from Mudéjar to Gothic. You'll see many such landmarks around Old Town, such as the 11th-century Alcázar (palace), the 14th-century Old Main Synagogue, and the 16th-century Segovia Cathedral, which dominates the skyline. After the tour, enjoy lunch in a local restaurant. You'll have the rest of the day free.

Day 8: Hike Sierra de Guadarrama, Wine Tasting

Venture into the mountains of Sierra de Guadarrama National Park

After an early breakfast, leave Segovia on a drive to Sierra de Guadarrama National Park. This 131-square-mile (340 sq km) protected area is known for its scenic hiking trails, which you'll take advantage of today. During this three-hour excursion, trek around pristine landscapes, including pine forests, clear water creeks, alpine meadows, granite rock formations, and glacial lagoons. That's to say, nothing of the exotic wildlife here—you might spot a deer or ibex.

After the hike, you'll transfer to another famous region near Segovia: the Ribera del Duero. This fertile area is one of the premier wine regions in Spain. Here, you'll visit a family-run winery for a two-hour tour and tasting. The visit includes learning the history of Segovian wines, the aging process, and of course, plenty of tastings paired with appetizers. Afterward, you'll return to Segovia.

Day 9: Drive to Madrid, Optional Activities

El Escorial
Stop in El Escorial and visit its sprawling monastery

In the morning, you'll get back in the car for the one-hour drive south to Spain's capital, Madrid. If you like, you can stop in El Escorial, a town nestled in the Sierra de Guadarrama mountains northwest of the city. There are a number of impressive landmarks to visit here, including 16th-century landmarks like the park of La Granjilla and the Royal Monastery of San Lorenzo de El Escorial. The latter is the most awe-inspiring building in the region.

Upon arrival in Madrid, you'll check into your hotel and have the rest of the day free to explore. Madrid is also a bastion of history dating back to the early Middle Ages. It abounds with music, art, culture, and, of course, excellent cuisine. If you like, start the tour in the city center and the Plaza Mayor, a grand plaza that was the heart of Old Madrid. Also, here is the 18th-century Royal Palace, the official home of the Spanish monarchs until 1931. You can tour this 3,418-room estate and visit the bed chambers, Royal Chapel, and the Hall of the Crown, which displays Charles I's crown, scepter, and throne.

Later, perhaps visit El Retiro Park. This 308-acre (125 ha) expanse is the green lung of Madrid and abounds with sculptures, fountains, and a lake. It also boasts a stately garden home to over 4,000 roses that bloom from May-June. Another fun activity is riding the Teleférico cable car from the district of Moncloa to Casa de Campo, Madrid's largest public park. And when you get hungry, visit the Mercado San Miguel, a covered market over a century old with 30 food stalls selling everything from tapas and seafood to pastries and fresh produce.

Day 10: Depart Madrid

Sun setting on Gran Vía, one of Madrid's main thoroughfares
Unfortunately, your epic road trip through Portugal and Spain has come to an end. At the appropriate time, you'll drop off your rental car and transfer to the airport in Madrid for your flight home. Adiós!

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Map of Spain & Portugal Road Trip: Porto to Madrid - 10 Days
Map of Spain & Portugal Road Trip: Porto to Madrid - 10 Days