Road Trip Through Spain & Portugal - 21 Days

Highlights

• See the highlights of Madrid and take a tapas tour
• Visit medieval churches and palaces in Toledo, Granada, and Seville
• Enjoy the beaches of Portugal's southern Algarve coast
• Tour Lisbon's markets and hear authentic fado music
• Spend time in romantic Porto and the Douro Valley wine region

Brief Itinerary

Detailed Itinerary

Day 1: Arrive in Madrid (Spain), Tapas Tour

Welcome to Spain! With thousands of years of history dating back to before the Roman Empire, you can bet this sun-kissed nation on the Iberian Peninsula is filled with culture. You'll arrive in Madrid, the nation's capital and itself a bastion of history dating back to the early Middle Ages. If you want a well-rounded introduction to Spain's music, art, culture, and cuisine, you can't do any better than Madrid.

Speaking of which, after the private transfer from the airport to your hotel, you'll head out on a guided tour to experience the most Spanish of culinary offerings: tapas (literally "tops" or "caps"). These are small plates of food served in bars, bodegas, and restaurants, often for free, accompanied by beer or wine. Madrid has its own tapas scene, which madrileños call picoteo ("to eat small bites").

Day 2: Guided City Tour, Free Afternoon in Madrid

In the morning, meet your guide and head out on a history and culture tour of Madrid. During this three-hour excursion, you'll discover landmarks, monuments, and other architectural marvels that date back to this city's founding in the 17th century and before. Along the way, your guide will reveal insight into how different time periods influenced Madrid's neighborhoods and buildings while pointing out the most exciting sights.

One historic area you'll visit is the Madrid de los Austrias. It was built in the 16th century during the reign of the Habsburg Dynasty's first ruler, Charles I. Located in the city center, it's home to one of the grandest plazas in Spain, the Plaza Mayor, which was once the heart of Old Madrid. Also, here is the 18th-century Royal Palace, the official home of the Spanish monarchs until 1931. You'll tour the grounds and interior of this 3,418-room estate, visiting the bed chambers, several salons, the Royal Chapel, and the Hall of the Crown, which displays Charles I's crown, scepter, and throne.

Day 3: Day Trip to Toledo

After an early breakfast, your driver will take you to the railway station in Madrid. Here, you'll catch a train a little over half an hour south to Toledo. This historic gem of a city was the capital of Spain in the 16th century and enjoys a dramatic location atop a gorge overlooking the River Tajo. This is where you'll be spending the day on a self-guided tour.

One interesting fact about Toledo: In the Middle Ages, it was known as the "City of the Three Cultures." It was a place where, legend has it, Christian, Muslim, and Jewish communities peacefully coexisted. You can see remnants of this in the old Arab, Muslim, and Christian monuments that still stand. These include the 15th-century Monastery of San Juan de los Reyes, the former Roman palace Alcázar de Toledo, and the Moorish Synagogue of Santa María la Blanca, which dates to the 12th century.

On your own, you can visit these historic landmarks as well as others, including the 13th-century Toledo Cathedral and the 12th-century Church of Santo Tomé. At the end of the day, you'll leave this UNESCO-listed city as you board a train back to Madrid.

Day 4: Train to Granada, Optional Activities

Return to the station in Madrid this morning and catch a train south for 3.5 hours to the southern Andalusia region and Granada. This is a city that rivals any other in Spain for history and beauty. Granada was once the last bastion of Al-Andalus (Muslim Spain) during the 400-year reign of the Moors, which lasted from 711 to 1086 CE. You can see examples of this history at Granada's most famous landmark, the Alhambra, which receives more than two million visitors annually.

Upon arrival at the station, a driver will pick you up and transfer you to your hotel. Then you can explore the city on your own. You can walk to most of Granada's most famous landmarks and neighborhoods. These include the Plaza Nueva (the oldest square in the city), the Albacín (the medieval/Moorish historic center), Barrio Realejo (the historic Jewish Quarter), and the 16th century Catedral de Granada, the largest and most opulent Roman Catholic church in the city.

End the day at a local eatery to enjoy some traditional tapas and adult refreshments. Bring your appetite—Granada is known for its huge portion sizes.

Day 5: Guided Alhambra Tour, Flamenco Show

In the morning, you'll head out on a guided tour of the Alhambra, a 26-acre (12 ha) Muslim fortress built atop a hill overlooking Granada that dates to the ninth century. It was rebuilt in the 14th century by the Nasrid Dynasty and served as a Moorish palace until 1492 when, after the Christian reconquest, it became the Royal Court of Ferdinand and Isabella (today it's a museum and UNESCO World Heritage Site). On a three-hour tour, you'll walk its grand halls and stroll the Generalife Gardens, which are filled with colorful flowers and fountains and offer panoramic views of the city below.

Later in the evening, you'll enjoy an authentic flamenco show. Granada is famous for its centuries-old caverns that doubled as music halls in the 17th and 18th centuries and where Roma musicians (some of the earliest practitioners of this musical style) performed for travelers. The tradition continues today, and it's at one of these rustic venues where you'll enjoy a performance that lasts a little over an hour.

Day 6: Free Day in Granada

Today is yours to enjoy Granada on your own schedule. If you like, head out for another walking tour to landmarks like the massive Granada Cathedral. Built in the 16th century, this Gothic/Renaissance marvel was constructed over the site of a mosque, and inside features grand marble columns and stunning stained glass windows. You can also return to Barrio Realejo and the Albacín. In the latter neighborhood are plenty of places to browse for authentic items like clothes, rugs, and glassware. You can also stop at one of its many tea houses for spiced coffee and churros con chocolate. 

Day 7: Pick Up Rental Car & Drive to Seville, Stop at White Villages

After breakfast, you'll embark on a memorable Andalusian road trip. Pick up your rental car and drive west to Seville, the awe-inspiring capital of Spain's Andalusia region. The drive takes about three hours, but you'll break it up with stops at a few of Spain's famous Pueblos Blancos (White Villages). Your first stop will be in Ronda, the capital of the Pueblos Blancos, which dates to the sixth century. It's a storybook locale carved from a mountain and overlooking a deep gorge. No less than Ernest Hemingway said of Ronda: "The entire town and as far as you can see in any direction is romantic background."

Then travel further west to Sierra de Grazalema, a national park and UNESCO Biosphere Reserve. The landscapes here are wild, featuring towing limestone peaks, deep gorges, and storybook hamlets. Next, visit Grazalema, a postcard village inhabited since Roman times. You'll leave the town on a mountain road called Puerto de las Palomas, where you can stop at viewpoints at 3,795 feet (1,157 m). Here, you'll have dramatic views over the provinces of Cádiz, Málaga, and Seville.

Continue through the mountains, stopping at the picturesque white village of Zahara de la Sierra. Located at the top of a hill, Zahara is famous for its lovely views and deep history (it dates to around 1282). You'll have time to walk around town, have a coffee, and visit a small olive oil factory that makes some of the best such oil in Andalusia. After marveling at the landscapes and snapping photos, you'll hop back in the car for the final leg of the journey to Seville. Upon arrival, you'll check into your hotel.

Day 8: Visit Seville's Cathedral & Alcázar

No trip to Seville is complete without visiting the city's iconic Moorish palaces and Gothic cathedrals. This 2.5-hour guided tour begins at the Seville Cathedral, a 15th-century Roman-Catholic church home to the tomb of Christopher Columbus. You'll also see La Giralda, the cathedral's looming bell tower. There's a noticeable stylistic difference between the two structures, as this 12th-century pillar was originally built as a minaret for the Great Mosque back when the Moors ruled Andalusia.

Then visit the Alcázar of Seville. Built over the site of a former Muslim fortress, this royal palace was commissioned for King Peter of Castile in the 14th century. It features well-manicured gardens, and the building is one of the nation's finest examples of Mudéjar architecture. Next, head to the fashionable Santa Cruz neighborhood, once the Jewish Quarter in the city. It's a colorful and well-preserved part of the historic center, with many options for cafés and tapas bars.

After completing the half-day excursion, you can return to your hotel and relax or continue to explore the town. If you decide to head out in the evening, do like the locals and complement tapas with a nightcap at a favorite watering hole.

Day 9: Day Trip to Córdoba

In the morning, you'll leave from the train station in Seville on a 40-minute journey northeast to Córdoba. Perfect for a day trip, this is yet another romantic city in the Andalusia region, filled with historic Mudéjar architecture. It also has a long and storied history, as it was founded by the Romans back in the second century BCE. Upon arrival, you can head out on a self-guided tour to visit the historic landmarks in this UNESCO World Heritage Site.

Highlights include the Mezquita (Mosque-Cathedral of Córdoba), a pagan temple that, in the eighth century, was converted into the great mosque of the Ummayad caliphate. Later it was transformed into a Catholic church. From the Mezquita, visit the 14th-century Alcázar de los Reyes. This is where Christopher Columbus met with the Catholic monarchs and was granted approval for his voyage west in search of the Indies. Its terraced gardens, fish ponds, flower beds, and orange trees offer great photo opportunities.

Day 10: Drive to Cádiz via Jerez de la Frontera

After breakfast, you'll hop in the car for the drive about 1.5 hours south from Seville down to the coastal city of Cádiz, the capital of the province of the same. On the way, you'll stop at the lovely hilltop city of Jerez de la Frontera. Famous for sherry wine production, Jerez is also home to the Royal Equestrian Academy, one of the premier riding schools in the country. Historic landmarks worth visiting here include the 11th-century Alcázar, Plaza de Arenal, and the Gothic/Baroque Cathedral of Jerez, which dates to the 17th century.

In the afternoon, you'll enjoy a sherry tasting. Sherry originated in Jerez, and a bodega is a must-visit if you want to learn more about Spanish wine culture. They've been making wine here since before the Roman times, and the sherry tradition in Jerez is over 2,000 years old. In fact, the word jerez means "sherry" in English. After the tasting, continue driving about a half hour south to the coast and Cádiz. This lively port town was founded by the Phoenicians over 3,000 years ago, and it was the site of the drafting of Spain's first constitution, which was passed in 1812.

Day 11: Free Day in Cádiz

Today you'll be free to enjoy Cádiz on your own. If the weather is nice, head to La Caleta, an inviting beach in the city center. There's also the option for a half-day sailing tour around the tranquil Bay of Cádiz and down the coast. The waters in the bay are tranquil, and a boat tour offers perfect relaxation—a trip that's even better while enjoying a glass of Cádiz's regional garum red wine.

In the evening, you can explore Cádiz's famous restaurant scene. Sit down at a local restaurant and enjoy delicious tapas like chicharrones (deep-fried pork rind) and goat cheese. Also, try tortitas (pancakes) and homemade chocolate cake. At the end of the day, you'll return to your hotel.

Day 12: Transfer to the Algarve (Portugal) & Pick Up Rental Car, Explore Lagos

Drop off your rental car this morning and meet your private driver for a four-hour transfer up the coast and east into Portugal. Your destination is Lagos, a colorful seaside village on the western side of Portugal's stunning Algarve region. Situated along the country's southern coast, this area is famous for its dramatic coastal cliffs, charming waterfront villages, unique rock formations, and great beaches.

Upon arrival, you'll pick up another rental car, then check in to your hotel and spend the rest of the day exploring. Highlights of Lagos include its charming inner-walled Old Town, pretty harbor, sandstone cliffs, golden beaches, delicious seafood restaurants, and buzzing nightlife. Locals are proud to say that Lagos has not succumbed to mass tourism like other areas of the Algarve, and the city still retains its distinctive character and laid-back charm.

Day 13: Boat Excursion to Benagil Caves & the Algarve Coast

See the highlights of the Algarve coast on a cruise to the world-famous Benagil Cave. In the morning, you'll transfer to the marina in the nearby city of Portimão and head out on a three-hour cruise. Along the way, you'll pass lovely beaches and unique rock formations at Praia da Marinha. Relax and enjoy the scenery as you cruise along this dramatic coastline. Then anchor in the romantic cove of João de Arens to explore the otherworldly Benagil Cave, followed by some swimming and snorkeling. At the end of the tour, you'll return to the marina and transfer back to Lagos. 

Day 14: Free Day in the Algarve

Today is yours to relax in Lagos or head deeper into the Algarve. Lovers of tranquility should visit the massive Costa Vicentina Natural Park. This protected area covers a whopping 182,857 acres (74,000 ha) of beaches, cliffs, rolling hills, and marshland that are a natural habitat for more than 750 species of flora and 200 species of birds.

You can also spend time in Lagos discovering its history, which dates to the 16th century. Stroll the cobblestoned streets, charming waterfront, and town squares. Near the center are several fine beaches to choose from. Pinhao, for example, lies in a peaceful and secluded cove, while Ponta da Piedade features dramatic sandstone cliffs and bright turquoise water. Also, Praia do Camilo is a gorgeous spot accessed by walking down 200 wooden steps to a sheltered sandy cove.

You could also head eastward along the Algarve for more beautiful sights and attractions. These range from golf courses to bustling resort towns and whitewashed villages offering mouthwatering cuisine and stunning coastal scenery.

Day 15: Drive to Lisbon, City Tour

In the morning, you'll drive north for three hours to Lisbon, the capital of Portugal. Located at the mouth of the Tagus River, Lisbon is four centuries older than Rome (the Phoenicians first settled in Lisbon around 1200 BCE). As such, there's plenty of history written on the cobbled streets here in the form of castles, forts, monasteries, plazas, and more. Upon arrival, drop off your rental can and transfer to your hotel in the city.

After settling in, you'll head out on a three-hour guided tour of the "City of Seven Hills." Led by an expert local guide, you'll travel to all corners of the city, from the waterfront Baixa district to the cobblestone alleys of the bohemian Bairro Alto. You'll also visit 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. 

Day 16: Visit Lisbon's Markets, Evening of Fado

Head out and discover the soul of Lisbon on a self-guided tour of its markets and bazaars. These are excellent places to meet locals and buy authentic food and souvenirs. In this city, the markets offer something for everyone, be it fresh produce, traditional handicrafts, vintage clothing, or contemporary urban arts and crafts. You can start at Mercado da Ribeira, the city's largest indoor marketplace. It spans a whopping 32,908 feet (10,000 m).

The most famous shopping hub is the Feira da Ladra flea market, which abounds with vintage clothes and quirky antiques. The market is held on Tuesdays and Saturdays in Campo de Santa Clara, near São Vicente de Fora Monastery. Also around Lisbon are smaller markets popular with a younger crowd, like the Feira das Almas, a monthly art and flea market. If you're here on a Sunday, visit the trendy market at LX Factory, where you can browse vintage items, artworks, handmade jewelry, and more.

Day 17: Day Trip to Sintra & Cascais

In the morning, your driver will pick you up for the ride to 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. Your day tour begins 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. 

After the palace, you'll head just south of Sintra to the fishing town of Cascais. This is the premier beach destination for holidaymakers from Lisbon, and it was once the coastal playground of Portuguese royalty. The many lavish mansions in the area have earned the region the nickname the "Portuguese Riviera." Another glamorous town in the area you'll stop at is Estoril, and you'll also visit the dramatic coastal cliffs of the Cabo de Roca. At the end of the day, you'll return to Lisbon.

Day 18: Train to Porto, E-Bike City Tour

After breakfast, you'll transfer to the railway station in Lisbon and catch a 3.5-hour train north to Porto. Sitting on the Douro River, the history of this colorful, romantic city dates back over 2,000 years. Upon arrival at the station, you'll transfer to your hotel in the city center. A little while later, explore Porto's cobbled streets and medieval landmarks on an e-bike tour around the city. The electricity will do most of the work as you zip around Porto on a three-hour scenic ride led by a local expert who will point out the cultural and historical landmarks of the city.

The tour will take you through Porto's historic center—a UNESCO World Heritage Site—where you can 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, Church of St Francis, and Bolhão Market, to name a few.

Day 19: Free Day in Porto

The day is yours to enjoy Porto however you wish. In the morning, you can head out for a self-guided walking tour of any landmarks you might have missed yesterday. Perhaps visit the Praça da Liberdade (Liberty Square), the city's largest and most impressive plaza. Other highlights include Rua Santa Catarina (the main shopping thoroughfare), Gomes Teixeira Square, and the Baroque Igreja dos Clérigos church, which dates to 1750.

Consider heading to one of Porto's waterfront wine cellars in the evening to taste world-famous port wine. You can participate in a one-hour experience during which a local guide will lead you through the wine's history as you sample various tawny and ruby ports in the tasting room. Afterward, enjoy dinner in Porto's historic center.

Day 20: Day Trip to Douro Valley, Winery & Boat Tour

Your driver will pick you up in Porto today 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 hourlong 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 21: Depart Porto

Unfortunately, you've reached the last stop on your grand tour of the Iberian Peninsula. At the appropriate time, a driver will pick you up from your hotel and transfer you to the airport in Porto, where you'll catch your flight home. Safe travels!

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