Soak up the sun as you explore the highlights of Portugal and Spain on this two-week adventure. Start in Lisbon, where you'll discover the city's historical attractions, markets, and fairs. Go hiking in Sintra and the Algarve, enjoy a catamaran cruise, and see the Ria Formosa Lagoon by bike. Then head to Spain for more city tours and cycling as you explore Seville, Carmona, and Granada. Finally, savor some tapas in Madrid, go ziplining in Toledo, and see Segovia by hot-air balloon.


  • Explore Lisbon's sights and history on a tuk-tuk tour
  • Cycle from Seville to Carmona along the famous Via Verde trail
  • Try delicious local specialties from Madrid at a "picoteo" (tapas crawl)
  • View scenic Segovia from above on a hot-air balloon ride

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon (Portugal) & Enjoy a Roots, Food & Cultural Walk Lisbon
Day 2 Guided Tuk-Tuk Tour, Explore Lisbon's Markets & Fairs Lisbon
Day 3 Sintra Heritage Hike Lisbon
Day 4 Drive to the Algarve, Hike Seven Hanging Valleys Trail Algarve
Day 5 Catamaran Cruise to Benagil & Carvoeiro Algarve
Day 6 Bike Tour of the Ria Formosa Lagoon Algarve
Day 7 Transfer to Seville (Spain) & Guided Visit Seville
Day 8 Cycle the Via Verde to Carmona by Electric Bike Seville
Day 9 Transfer to Granada & Hike the Caminito del Rey Granada
Day 10 Tour the Alhambra & Generalife Gardens, Sacromonte Cave Flamenco Show Granada
Day 11 Train to Madrid, Old Madrid Tour & Tapas Culinary Experience Madrid
Day 12 Guided Visit of Toledo & Ziplining over the Tagus River  Madrid
Day 13 Segovia City Tour & Hot-Air Balloon Ride Madrid
Day 14 Depart Madrid  

Detailed Itinerary

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

Praca do Comercio, Lisbon's main square
Praça do Comércio, Lisbon's main square

Welcome to Portugal! Medieval castles, cobblestone villages, captivating cities, and golden beaches await. Meet your driver at Lisbon airport and transfer to your hotel, then prepare to explore two of Lisbon's most ancient neighborhoods, Mouraria and Baixa, on a small-group food tour.

Take a trip through time as you stroll from the historic alleys of the 12th century into the bustling modern-day city, soaking up the laid-back vibes of each area and pausing to sample authentic Portuguese dishes and snacks. In a stroll off the beaten path, you'll discover why Mouraria is such a unique place, as it is the birthplace of Fado music and the most multicultural neighborhood in Lisbon. The walk includes six stops for tastings at favorite local haunts, where you'll learn more about the staples of Portuguese cuisine and its many influences.

Day 2: Guided Tuk-Tuk Tour, Explore Lisbon's Markets & Fairs

Guided Tuk-Tuk Tour
Enjoy a guided tour of Lisbon by tuk-tuk

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 downtown Baixa to the cobblestone alleys of the bohemian Bairro Alto. Discover the city's fascinating history and hidden corners, and stop at stunning panoramic viewpoints like São Pedro de Alcântara, Parque Eduardo VII, Senhora do Monte, and Santa Luzia. Use the rest of the day to explore Lisbon at your own pace. Besides getting lost in the city on foot, you can seek out several unique places.

The markets and fairs are excellent spots to meet locals and buy authentic food and souvenirs. The best-known fair is the Feira da Ladra flea market, where you can find everything from vintage clothing to quirky antiques. Countless small markets are popular with a younger crowd, such as the Feira das Almas and the trendy Sunday market at LX Factory, where you can find vintage clothing and products made by young and upcoming craftspeople. Don't forget to visit the local produce markets, including the daily Mercado da Ribeira and the fashionable food hall Time Out Market.

Day 3: Sintra Heritage Hike

Sintra Heritage Hike: Hidden Secrets
View of Pena Palace in the mist

Today, explore the palaces and villas of Sintra, which have enchanted visitors for centuries. This place has inspired poets and writers such as Lord Byron, who fell in love with Sintra and lived there for some time. Enjoy a 6-mile (10 km) scenic hike to the Moorish Castle dating back to the eighth century, and admire the Pena Palace at the top of the mountain, a region highlight. The trek will take you through dense forests as you discover the wonders of the natural environment here. 

Day 4: Drive to the Algarve, Hike Seven Hanging Valleys Trail

Praia do Camilo, Lagos
Praia do Camilo, Lagos

Pick up your car rental to make the three-hour drive to the Algarve, a maritime region along Portugal's southern coast. Upon arrival, check into your hotel and explore independently for the rest of the day. Lagos is one of the main destinations in the Algarve and is known for its charming inner-walled old town, pretty harbor, dramatic sandstone cliffs, beautiful beaches, 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 it still retains its distinctive character and laid-back charm.

Nearby, trek the Seven Hanging Valleys Trail, a 3.5-mile (6 km) clifftop walk on the Algarve's central coast for views over turquoise seas. Your first steps on the boardwalk from Vale de Centeanes beach lead you away from the din of modern life and into the nature of salty air, crashing waves, and multihued rock formations. Snap pics of the Alfanzina Lighthouse and the twin arches over the water near Praia da Mesquita

Day 5: Catamaran Cruise to Benagil & Carvoeiro

Benagil Caves
View of the Benagil Caves
Head off on a cruise today from Portimão to the Benagil Caves. On the way there, take in the vistas of the beaches of Carvoeiro, Algar Seco, Benagil, and Praia da Marinha, as well as the Alfanzina Lighthouse. Take a chance to partake in water-based activities as you anchor in the lovely coves of João de Arens. Here, you can go for a swim and try out snorkeling and standup paddleboarding. Enjoy soaking up the sun on twin sunbathing nets as you skirt the breezy coastline. 

Day 6: Bike Tour of the Ria Formosa Lagoon

Eco Biking in the Ria Formosa
Biking in the Ria Formosa

Today, you'll discover the rich landscape of the Ria Formosa, known as one of the "Seven Natural Wonders of Portugal," by bike. Accompanied by an expert guide, explore the surroundings, from saltpans to beaches, as you're treated to sights of birdlife and the incredible range of wildlife these protected lands offer. Migratory birds use the park as a resting area, and you'll find a broad diversity of species nesting here.

Visit the Tide Mill, which is entirely restored and offers a panoramic view of the barrier islands of Olhão. Afterward, head to the Chalé Dr. João Lucio, built in 1916. The house has four entries at the four cardinal points and is a scenic spot with interesting architecture. 

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

Day 7: Transfer to Seville (Spain) & Guided Visit

Sevilla's historic architecture
Sevilla's historic architecture

Meet your private driver at your hotel and prepare for the fairly short drive to Seville in Spain. Once you arrive, get acquainted with Seville on a guided walking tour and learn about its 2,000-year history. During the tour, you'll admire (from the outside) 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. You'll then walk to the orange tree-filled Santa Cruz neighborhood, known as the Jewish Quarter, with its narrow streets and quaint squares.

Explore this colorful and well-preserved part of the historic center, with its many cafés and tapas bars—the perfect excuse to take a break and enjoy some small plates and local wine. You'll conclude your walk at the banks of the Guadalquivir River. You'll also visit the Alcazar, a grand monument included by UNESCO in its list of World Heritage monuments, and a set of palaces and gardens representing a harmonious synthesis between Christian and Muslim cultures.

Day 8: Cycle the Via Verde to Carmona by Electric Bike

A panoramic view of Carmona in southern Spain
A panoramic view of Carmona in southern Spain

Cycle past rivers and castles and olive and orange groves as you travel from Seville to Carmona. This route has existed from time immemorial, as it was the first staging post from Seville to Cordoba and Granada. Nobles, merchants, writers, Romans, Christians, and Muslims have all traveled this path—on foot, on horseback, or by train.

Follow along the route's greenways by e-bike, tracing the course of the Guadaíra River until you arrive in the rolling lowlands of Seville, from which you'll ride onward to Carmona. Along the way, stop to check out historic towns, castles, water mills, and an aqueduct while enjoying the surrounding landscapes. Then, return by train to Seville, accompanied by your local guide (there's also the option of returning by car). 

Day 9: Transfer to Granada & Hike the Caminito del Rey

The Caminito del Rey walkway in the province of Málaga
The Caminito del Rey walkway in the province of Málaga

Today, you'll embark on a road trip through some of Andalusia's most enchanting locales. Take in the views as your transfer drives through olive groves, rolling meadows, cork forests, and around mountains. Your destination is Granada, located about two hours from Seville. However, you'll stop en route for some adrenaline-pumping hiking at the Caminito del Rey—a network of walkways built along a deep gorge carved out by the Guadalhorce River. At times, the gorge reaches harrowing depths of 2,297 feet (700 m).

Arrive at the northern entrance and put on your safety equipment. Then, it's time to head off along the trail. As you hike, you'll be treated to incredible views down the gorge to the river winding through the valley below. This one-way trail typically takes about three to four hours to complete. Afterward, you'll continue to Granada, where you'll check into your hotel and take the rest of the day to relax and recharge.

Day 10: Tour the Alhambra & Generalife Gardens, Sacromonte Cave Flamenco Show

Generalife Gardens of the Alhambra in Granada
Generalife gardens of the Alhambra in Granada

Granada was once the last bastion of Al-Andalus (Muslim Spain). Today, you'll see striking examples of this history on your tour of the UNESCO-listed Alhambra palace. Dramatically topping a hill overlooking Granada, this imposing Muslim fortress 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.

Your tour will take you through the grand buildings and allow you to stroll the beautiful Generalife park and gardens, vibrantly filled with flowers, fountains, and pathways. Sensational panoramic views of Granada below open up before you. Later, head to the Sacromonte neighborhood, home to the zambra style of flamenco dancing. Here, you'll watch an authentic flamenco show performed inside a cave, a tradition dating to the 18th and 19th centuries. 

Day 11: Train to Madrid, Old Madrid Tour & Tapas Culinary Experience

Royal Palace of Madrid at night
Royal Palace of Madrid at night

Make your way to the train station in Granada and board the 3.5-hour service to Madrid. Upon arrival, head to your hotel to check in and prepare for a tour of Madrid's oldest barrio, the Austrias neighborhood. As you wander along the atmospheric, medieval streets, you'll be transported back to the year 711, when Madrid was under the rule of the Iberian Caliphate. Learn how Madrid became the capital of Spain in 1561, discuss the dark days of the Inquisition, and finish in 1725, when the oldest restaurant in the world, Restaurante Sobrino de Botín, first opened its doors. 

Later, enjoy a walking food tour where you'll have the chance to experience a picoteo. "Picoteo" originates in the verb "picar," which means eating small bites from several shared plates. This is also known as a tapeo or tapas crawl. Your culinary journey starts at a traditional bodega serving delicious Spanish tapas. Over the next three stops, you'll try some excellent meat and fish dishes from Madrid, along with cold draft beer and local wines. To conclude your picoteo, finish at a traditional restaurant featuring cuisine from the north of Spain.

Day 12: Guided Visit of Toledo & Ziplining over the Tagus River 

View over Toledo
View over Toledo

Upon arrival in Toledo this morning, meet your guide as you exit your train to the platform. In the Middle Ages, Toledo was known as the "City of the Three Cultures." According to legend, Christian, Muslim, and Jewish communities once peacefully coexisted here, and this history is apparent in the old Arab, Muslim, and Christian monuments that still stand. These include the 15th-century Monastery of San Juan de los Reyes, the Alcázar de Toledo (a former Roman palace), and the Moorish Synagogue of Santa María la Blanca, which dates to the 12th century.

Accompanied by an expert guide, you'll visit these historic landmarks and others, including the grand 13th-century Toledo Cathedral and the 12th-century Church of Santo Tomé. Throughout it all, you'll tour the ancient streets of an incredible, UNESCO-listed city that could aptly be described as an open-air museum. After the guided part of the visit, you'll have time for lunch before flying over the Tagus River on a zipline. Enjoy the adrenaline rush, then take some time to explore the city on your own before returning to Madrid. 

Day 13: Segovia City Tour & Hot-Air Balloon Ride

View Segovia from the sky in a hot air balloon
View Segovia from the sky in a hot-air balloon

Transfer to Segovia today, and explore the city by land and air on an action-packed day trip. The adventure starts in the morning with a scenic hot-air balloon ride as you let the wind guide you over the spires, aqueducts, and rolling fields. After a toast with a bit of bubbly cava, enjoy a complete city tour, stopping at iconic sites like the Roman Aqueduct, Segovia Cathedral, and Royal Alcazar as you wander the medieval streets. In the evening, return to Madrid. 

Day 14: Depart Madrid

The city skyline and sunrise at Cibeles Fountain town square in Madrid
The city skyline and sunrise at Cibeles Fountain town square in Madrid
After two weeks of exciting adventure, prepare to say goodbye to the Iberian Peninsula. A driver will pick you up at your hotel for a transfer to Madrid's international airport at the designated time. ¡Buen viaje!  

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Map of Spain & Portugal Adventure: Lisbon, Algarve, Seville, Granada & Madrid - 14 Days
Map of Spain & Portugal Adventure: Lisbon, Algarve, Seville, Granada & Madrid - 14 Days