Get ready for an epic odyssey through the culture, flavors, history, and music of three neighboring countries. This three-week itinerary begins in Portugal with food/wine tours of Lisbon and Porto, plus riverboat rides and coastal hikes. Then you're off to Spain to discover the highlights of Madrid, Barcelona, and Seville before hopping the Strait of Gibraltar and finishing in style at the souks and medinas of Morocco.


  • Dine with locals and take food tours in Porto and Lisbon
  • Take a river cruise in the Douro Valley and enjoy wine tastings
  • Explore the highlights of Madrid, Barcelona, and Seville
  • Stroll the medinas of Morocco's historic cities like Marrakesh
  • Browse the souks in Tangier, Fes, and Chefchaouen 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon (Portugal), Food & Cultural Walk Lisbon
Day 2 Guided Tuk-Tuk Tour, Dinner With a Local Lisbon
Day 3 Day Trip to Sintra, Forest Hike Lisbon
Day 4 Transfer to Porto via Coimbra Porto
Day 5 Porto Architecture Tour, Visit Matosinhos Beach Porto
Day 6 Day Trip to the Douro Valley, Wine Tasting & River Cruise Porto
Day 7 Fly to Barcelona (Spain), Tapas Tour Barcelona
Day 8 Barcelona Bike Tour, Visit Sagrada Família Barcelona
Day 9 Free Day in Barcelona Barcelona
Day 10 Train to Madrid, Old Madrid Tour Madrid
Day 11 Free Day in Madrid Madrid
Day 12 Day Trip to Toledo, Guided Tour Madrid
Day 13 Train to Seville, Guided Bike Tour Seville
Day 14 Olive Oil Tasting & Flamenco Experience Seville
Day 15 Transfer to Tangier (Morocco), Guided Tour Tangier
Day 16 Transfer to Chefchaouen, Visit Caves & Tétouan Chefchaouen
Day 17 Transfer to Fes Fes
Day 18 Fes Medina Tour Fes
Day 19 Transfer to Marrakesh, Guided Tour Marrakesh
Day 20 Optional Day Excursions Marrakesh
Day 21 Depart Marrakesh  

Detailed Itinerary

Day 1: Arrive in Lisbon (Portugal), Food & Cultural Walk

Lisbon is one of the oldest cities in Europe and filled with medieval landmarks

Welcome to Portugal! This country at the edge of the Iberian Peninsula may be small, but don't let that fool you. It boasts a rich heritage and the longest empire in European history—almost 600 years. You'll arrive in the capital of Lisbon, a city founded by the Christians in 1147—though its actual settled history dates back around 2,700 years. That makes Lisbon even older than Rome. Upon arrival at the airport, a driver will be waiting to transfer you to your hotel in the city center.

After settling in, you'll hit the cobbled streets on a half-day guided food tour. You and your small group will step back in time as you stroll ancient neighborhoods like the city center and Mouraria, also known as the Moorish Quarter. Throughout the expedition, you'll sample authentic Portuguese dishes and snacks like bacalhau (salted codfish) and the famous bifana (a sandwich of sautéed pork). In total, you'll stop at six local haunts where, besides sampling delicious tidbits, you'll learn the history of Portuguese cuisine.

Day 2: Guided Tuk-Tuk Tour, Dinner With a Local

Guided Tuk-Tuk Tour
Hop in a tuk-tuk and zip around the seven hills of Lisbon

Explore the "City of Seven Hills" in style today by electric tuk-tuk. Led by a knowledgeable guide, you'll zip through the charming capital's modern and historic districts, from the neoclassical avenues of Baixa to the cobblestone alleys of bohemian Bairro Alto. Discover the city's fascinating history and hidden corners, and stop at panoramic viewpoints such as São Pedro de Alcântara, Parque Eduardo VII, Senhora do Monte, and Santa Luzia.

Afterward, explore Lisbon at your own pace. Later, you'll experience the warm hospitality of a local Portuguese family when you join them for a traditional meal at home. This is a unique opportunity to learn about the local cuisine and culture while breaking bread with the family and other guests in an intimate setting. Exchange stories and experiences, forge lasting connections, and immerse yourself in daily life over a three-course meal paired with local wine.

Day 3: Day Trip to Sintra, Forest Hike

Sintra's Pena Palace is one of the most famous landmarks in Europe

After breakfast, your driver will pick you up for the 30-minute drive out of the city to Sintra. This UNESCO World Heritage Site is nestled in the forested foothills of the Sintra Mountains and is dotted with fairy-tale palaces and extravagant villas. You'll explore the area on a 6-mile (10 km) hike that will take you to the Moorish Castle, which dates to the eighth century.

As you walk, you'll also be treated to magnificent views of Pena National Palace, which is perched on a hilltop. This bright yellow and pink building was built in 1854 and features ornate turrets and sculptures. At the end of the hike, you'll have lunch and return to Lisbon.

Day 4: Transfer to Porto via Coimbra

Coimbra is an attractive city overlooking the Mondego River

In the morning, you'll leave Lisbon and transfer north to Porto. The trip takes about four hours, but you'll stop halfway through in Coimbra to stretch your legs and have lunch. Sitting on a hill overlooking the Mondego River, this former medieval capital wears its prominent role in Portuguese history on its sleeve, as witnessed by its stately buildings that date back nearly a millennium.

The star of Coimbra is its 13th-century university, which is regarded as the country's greatest. You can visit its Baroque library, which is home to an incredible collection of over 200,000 books. Next door is the 12th-century Chapel of Saint Michael, which is also worth the visit. After touring the highlights and having a bite to eat, you'll continue on to Porto. Sitting on the Douro River, the history of this colorful, romantic city dates back over 2,000 years. Upon arrival, you'll transfer to your hotel and will have the rest of the day free.

Day 5: Porto Architecture Tour, Visit Matosinhos Beach

Tour some of the many highlight buildings in colorful Porto

In the morning, you'll embark on a half-day walking tour of Porto. This excursion focuses on the architectural marvels and historical landmarks that have contributed to Porto earning UNESCO World Heritage Status. And what better person to point out these highlights than an expert local architect? 

That's who you'll have as your guide today as you start in the heart of the historic center on Aliados Avenue. From there, your guide will lead you to Art Deco gems, the Rivoli Theater and the Old Cinema Batalha. Then visit the Portuguese Center for Photography, which is located in a former prison and exhibits works from local and foreign photographers. The last stop on the tour is along the Douro River and the waterfront Ribeira neighborhood, known for its colorful houses and buzzing nightlife scene. You'll also have the option to take a scenic cable car ride over the waterfront.

Later, you'll travel a few short miles from the center of Porto to the coast and the resort area of Praia de Matosinhos. This beach is where Porto's residents come to play. A major source of the region's seafood, there's a great market here, as well as many restaurants specializing in fresh fish. It's also a popular spot to ride waves and offers many surf schools and board rentals. After spending some time relaxing on the beach, you'll return to Porto at the end of the day.  

Day 6: Day Trip to the Douro Valley, Wine Tasting & River Cruise

Cruise along the vineyards of the Douro Valley and enjoy a wine tasting

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 authentic Portuguese cuisine. Then hop on 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.

Day 7: Fly to Barcelona (Spain), Tapas Tour

Tapas are meant to be shared with friends and family

After an early breakfast, you'll transfer to the airport and catch a two-hour flight to Barcelona. Welcome to Spain! You're now in the capital of the Catalonia region. This coastal gem is filled with history, culture, and fun, so much so that it's one of Europe's most popular vacation cities. Upon arrival at the airport, a driver will pick you up and transfer you to your hotel.

Hopefully, you've brought your appetite because now it's time to embark on a three-hour tapas tour. Tapas bars are an integral part of the social fabric in Spain—places where friends, family, and colleagues socialize over a few small plates of food paired with cañas (glasses of beer) and wine. After meeting your guide, you'll walk around some of Barcelona's historic neighborhoods, like the Gothic Quarter, stopping at local bodegas, bars, and restaurants. This is truly an authentic picoteo (tapas crawl).

Must-try tapas during this culinary adventure include patatas bravas (fried potatoes with aioli), gambas (prawns), calamari, cured ham, croquettes, mussels, and chorizo. Be sure to save room for a traditional Spanish dessert like crema Catalana, a sweet custard made with oranges and cinnamon that's Spain's answer to the classic crème brûlée. At the end of the tour, you'll return to your hotel.

Day 8: Barcelona Bike Tour, Visit Sagrada Família

The Gaudí-designed Sagrada Família is one of the most famous buildings in Spain

Embark on a guided bicycle tour of Barcelona this morning. It's just you and your guide on a three-hour tour that passes through historic and popular neighborhoods like the medieval Gothic Quarter and trendy Raval and El Born. Along the way, your guide will point out historic highlights, including Roman ruins, the grand Plaça Reial, and the Gothic Barcelona Cathedral, which dates to the 13th century.

But the tour doesn't end here. You'll cycle from the Gothic Quarter through Ciutadella Park, one of the largest green spaces in the city, all the way to Barceloneta Beach. This is the main urban beach, and it's always a hub of activity, lined with cafés, beaches, bars, and discos. Cycling along the promenade fronting the water is the perfect way to cap your two-wheeled city tour.

Afterward, you'll leave the bike and head over to the city's greatest monument, La Sagrada Família, a spectacular Roman Catholic church and UNESCO World Heritage Site designed by Catalan architect Antoni Gaudí. During a tour of the building, you'll learn all about Gaudí and his jaw-dropping masterpiece. Despite construction on the church beginning in 1882, it's still technically under construction and was only consecrated in 2010.

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

Day 9: Free Day in Barcelona

Barcelona's Arc de Triomf
The city's Arc de Triomf was built for the 1888 Barcelona World Fair
Today is yours to enjoy Barcelona on your own schedule. If you like, you can visit other Gaudí architectural landmarks like Park Güell and Casa Milá. Other must-visit highlights 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 10: Train to Madrid, Old Madrid Tour

Madrid Palace at Night
The Royal Palace of Madrid is one of the historical highlights of the city

In the morning, head to the station in Barcelona and catch a 2.5-hour train ride to Madrid. Spain's capital boasts a rich history dating back long before the Middle Ages. From around the eighth to the 11th centuries, this territory was under Muslim rule, and before that, it was the site of a Roman conquest that started in 218 BCE. On arrival at Atocha Station, a driver will pick you up and take you to your hotel in the city. Then you'll head out for a very special walking tour to learn more about Spain's deep history.

You'll meet your guide in the Austrias neighborhood, Madrid's oldest barrio. Here you'll walk in the footsteps of history and get a sense of what life was like during the 16th-century Golden Age under the Habsburg Dynasty. You'll visit the most famous landmarks of Madrid's old city center, including the Plaza Mayor. As you go, your guide will reveal historical details, such as what the city was like during the darkest days of the Inquisition. The 1.5-hour tour ends fittingly at Restaurante Botín. Having opened its doors in 1725, it's the oldest restaurant in the world.

Day 11: Free Day in Madrid

Spend a day enjoying the highlights of Madrid, like the Plaza Mayor

This is another free day to enjoy the city—and there are plenty of options for culture and fun. Madrid 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.

If you like, you can go shopping and see a show at glitzy Gran Vía, Madrid's answer to Broadway. Here, you'll find many theaters showing plays and musical productions. And when the hour gets late, you can revel in the city's nightlife scene. Some of the best areas for bars and clubs include Huertas and Chueca.

Day 12: Day Trip to Toledo, Guided Tour

Toledo, Spain
Toledo enjoys a privileged location on the Tajo River

Hop on a train this morning for the half-hour journey through the countryside to Toledo. This UNESCO World Heritage Site dates back to Roman times and was the capital of Spain in the 16th century. Toledo's cluster of clay-rooftop buildings, cobbled lanes, and church spires are crowded onto a hilltop overlooking the Tajo River and encircled by protective walls you enter through massive iron gates.

Once here, you'll meet your guide for a tour of the "City of the Three Cultures." Toledo earned this nickname because throughout history Christian, Muslim, and Jewish communities all peacefully coexisted here. As such, the city is crammed with religious buildings, including the 12th-century Iglesia de Santo Tomé, the Moorish Sinagoga de Santa María la Blanca, considered the oldest synagogue in Europe, and the grand 13th-century Toledo Cathedral.

You'll also visit the former Roman palace Alcázar de Toledo and the 15th-century Monasterio de San Juan de los Reyes, a cloistered monastery now returned to the Franciscan order and inhabited by monks. As you wander the streets and central plaza, Zocodover, you'll pass shops selling Toledo's famous products: marzipan and medieval weapons. Add an optional swordsmith experience or zipline adventure over the river to complete your Toledo adventure, then return to Madrid for the evening. 

Day 13: Train to Seville, Guided Bike Tour

See Seville on two wheels!
Hop on a bicycle and ride around Seville's highlights, like Plaza de España

After breakfast, you'll return to Atocha Station. This time you'll catch a train south into Spain's southern Andalusia region and its capital of Seville. At the end of the three-hour trip, you'll transfer to your hotel in the city and have time to relax and unwind.

Later, meet a local guide and hop on a bike for a half-day cycling tour of one of Spain's most romantic cities. Hit the road and pedal around this ancient metropolis, whose historic center dates back to the eighth century BCE. You'll cycle along scenic areas and landmarks like the Plaza de España, Guadalquivir Riverfront, Las Setas Marketplace, Plaza de San Francisco, and Seville's most beautiful gardens and parks.

During the excursion, your expert guide will share anecdotes and explain the mysteries and stories that define Seville. Overall, it's a fun, educational, and healthy way to get a feel for the city. Following the tour, you'll have the rest of the day free. If you like, take a long paseo (stroll) along Seville's ancient streets.

Day 14: Olive Oil Tasting & Flamenco Experience

Taste some of the finest olive oils in Spain

In the late morning, you'll head to Seville's historic center to visit an olive oil workshop. Spain's olive oils are some of the most prized in the world, and you'll discover their quality during a tasting hosted by a local extra virgin oil producer. During this fun workshop, you'll learn the characteristics of different Andalusian olive varieties, such as picual, arbequina, hojiblanca, and picudo. After the one-hour tasting session, sit for a traditional Andalusian lunch of various tapas—complimented by more delicious olive oil.

After some free time in the afternoon, head out for an evening flamenco experience. This musical style enjoys a rich heritage that dates back to the ninth century when the music and dances of immigrants in Andalusia mixed with the cultures of local Moors and Jews. Over the centuries, the intermingling of these different influences synthesized to produce the style of flamenco that has come to define Spanish folkloric music today. You'll witness this captivating performance in one of Seville's famous tablaos—(flamenco venue).

Day 15: Transfer to Tangier (Morocco), Guided Tour

Travel to Tangier, one of the most exciting cities on the Moroccan coast

Wake up early and meet your driver for the 2.5-hour ride from Seville to Tarifa, the southernmost point in continental Europe. At the port, you'll board a ferry for the six-hour ride across the Strait of Gibraltar to Morocco. Your destination is Tangier, a dynamic coastal city full of contradictions. Here, you'll find everything that defines Morocco with a dash of French and Spanish culture. Upon arrival, you'll transfer to your hotel and then head out and explore.

On a three-hour tour, your personal guide will lead you to historic districts like the kasbah (fortress) and medina (walled old town). You'll visit highlights like the 17th-century Sultan's Palace, now a museum featuring a vast collection of antiquities from throughout Moroccan civilization. Continue strolling through the narrow lanes leading to Bab Bhar (Gate to the Sea), which offers fantastic views of the Strait of Gibraltar, the Iberian Peninsula, the port of Tangier, and the Ville Nouvelle (New Town).

Throughout the tour, your guide will lead you to hidden corners of the city filled with tiny restaurants, textile studios, communal ovens, and other cultural minutiae far off the tourist trail. By the end of the experience, you'll begin to understand the city like a local.

Day 16: Transfer to Chefchaouen, Visit Caves & Tétouan

Wander the enchanting backstreets and alleys of Morocco's "Blue City"

After breakfast, your driver will pick you up for a scenic two-hour road trip into the stunning Rif mountains and Chefchaouen, the famous "Blue City" of Morocco. Its name translates to "two horns," referencing the two mountain peaks looming over the city. Drawing an artsy, bohemian crowd, Chefchaouen is famous for its small-village feel and blue-washed buildings that look straight out of Biblical times (though it was founded in 1471). For these reasons, it's regarded as one of the prettiest cities in Morocco.

On the way, you'll make a couple of stops at regional highlights. This first is the famous Caves of Hercules, located just a few miles outside Tangier. This dramatic cave complex is part human-made and part natural. It's said that the ancient Phoenicians carved its dramatic opening overlooking the sea, and local legend states that the Greek god Hercules once took a rest here between his famous exploits. After the caves, you'll stop at Tétouan, a jewel of a town at the foot of the Rif mountains near the sea. Its ancient medina is a UNESCO World Heritage site that looks like it hasn't changed in several centuries. 

After exploring Tétouan, you'll continue to Chefchaouen and check into your hotel. Then you're free to walk around the city's delightful medina, known for its medley of Moroccan and Andalusian influences. You'll see it in the red-tiled roofs, bright-blue buildings, and narrow lanes converging on the busy Plaza Uta el-Hammam with its restored kasbah. You'll also want to peruse the souks (markets) and dine in local restaurants, of which there are many. 

Day 17: Transfer to Fes, Optional Activities

On your way to Fes, stop to admire the Roman ruins of Volubilis

In the morning, meet your driver for the four-hour ride south from Chefchaouen to Fes. This is one of Morocco's famous Imperial Cities—places that at one time were the country's capital. Fez was the capital for over four centuries beginning in the 13th century, and today it remains a cultural and religious center.

During the drive, you'll stop for a tour of Volubilis, a World Heritage Site containing Morocco's best-preserved Roman ruins. Wander this 103-acre (42 ha) archaeological site and explore the former town's large merchant homes and temples as you admire its many colorful mosaics. Then, continue to the nearby town of Moulay Idriss to see where the ruler Moulay Idriss I introduced Islam to the region in 789 CE. Next, transfer to Meknes, a city founded in the 11th century by imperial Berbers as a military settlement. Explore the medina and visit the monumental city gates, which date to the 18th century.

Your final stop is Fes. Before settling into your riad (traditional Moroccan house with an interior courtyard), you'll drive up to the Marinid Tombs. The ruins of these monumental tombs are perched on a hill overlooking the city and from which you can enjoy panoramic views of Fes' medina. On the hillside below, you may even see leather drying in the sun—the last step in the tanning process. Then make your way into the bustling medina and spend time wandering Fes' charming streets. Enjoy dinner at your riad, followed by some well-deserved relaxation.

Day 18: Fes Medina Tour

Dye pots used in Fes' famous tanneries, which date to the 11th century

After breakfast, you'll meet your personal guide for a half-day walking tour of Morocco's oldest Imperial City (it was founded in the eighth century). The medina in Fes is a UNESCO World Heritage Site and one of the most well-preserved in the Arab world. This is because little of Fes has been refurbished over the centuries, which means that winding its warren of narrow streets is like stepping back in time.

Your guide will lead you through the medina's two quarters: Fes el Bali and Fes el Jdid. Here, you can browse the iconic souks (markets) whose vendors sell everything from spices and fresh produce to leather goods, ceramics, medicines, and more. Many are concentrated together, and you're bound to see artisans at work in their small shops. You'll also visit the Mosque and University of al-Qarawiyyin, which was founded in 859 and is the oldest operating university in the world.

After a break for lunch, you'll explore the medieval masterpieces of Bou Inania and Al Attarine madrasas, as well as the Najarin Fountain with its mesmerizing zellige tile patterns. The best way to end the day is by watching the sunset from the Merenid Tombs in the north or from the 16th-century Borj Sud fort in the south. Both viewpoints offer fantastic views of this dynamic city with timeless roots.

Day 19: Transfer to Marrakesh, Guided Tour

Visit Marrakesh's main square, Jemaa el-Fnaa, where all the action is

Wake up early today and depart Fes on a 5.5-hour transfer to Marrakesh. The second-largest city in Morocco, this is also one of the country's four Imperial Cities—places that, at one time or another, were the country's capital. Marrakesh was the capital at various times, starting with its founding in the mid-11th century. Today, the nation's capital is Rabat.

Upon arrival at the airport, a driver will pick you up and transfer you to your hotel. Then you'll head out on a half-day tour of the "Red City." Your local guide will lead you to popular areas like bustling Jemaa el-Fnaa, the main square in the city's medina. Nearby is the iconic Koutoubia Mosque, which dates to 1147. Just south of it is the kasbah, home to historic landmarks like the Saadien Tombs, Bahia Palace, and the Jewish Quarter.

Throughout the tour, you'll browse the souks and vendors in the merchant districts. You'll also visit Marrakesh's famous tanneries. The city is known for its leather goods; local families have been plying this trade since the 11th century. Another fun stop is at Majorelle Garden, which French fashion designer Yves Saint Laurent once owned. You can wander around this 2-acre (1 ha) garden filled with sub-tropical plants, bamboo, lilies, and palms. At the end of the tour, you'll return to your hotel.

Day 20: Optional Day Excursions

Adobe Berber village of the Atlas Mountains
Visit traditional adobe Berber villages in the Atlas mountains

Marrakesh is surrounded by vast deserts and dramatic mountain landscapes, which make for great day trips. You'll have your pick of some fun options for day tours. Perhaps hit the road to the Ourika Valley and Atlas mountains, where you can visit Berber markets and waterfalls and enjoy a sunset camel ride. Another scenic drive will take you over the Tizi n'Tichka mountain pass to Ouarzazat, a beautiful mud-brick city featured in productions like "Gladiator" and "Game of Thrones."

Or, if you like, travel to the coast and Essaouira, a well-preserved fortress city overlooking the ocean. Here, you can laze on nearby beaches and take a stroll along walk the waterfront. Also, be sure to visit its famous 18th-century defensive forts like the Borj El Barmil and the Skala de la Kasbah.

Day 21: Depart Marrakesh

The iconic Koutoubia Mosque at sunset
Your epic journey across Portugal, Spain, and Morocco has reached the end of the line. Enjoy one last Moroccan breakfast in Marrakesh before transferring to the airport, where you'll catch your flight home. Until next time!

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Map of Cultural Highlights of Portugal, Spain & Morocco - 21 Days
Map of Cultural Highlights of Portugal, Spain & Morocco - 21 Days