Discovering Iberia: A 20-Day Journey Through Madrid and Portugal
Welcome to an unforgettable journey through the Iberian Peninsula, where the vibrant cultures of Spain and Portugal await. This 20-day itinerary will take you through the bustling streets of Madrid, the historic charm of Lisbon, and the scenic beauty of Porto. From world-renowned museums and architectural wonders to delectable cuisine and lively local traditions, this trip promises a rich tapestry of experiences.
Madrid, the capital of Spain, is a city that seamlessly blends its rich history with modern vibrancy. Known for its stunning architecture, world-class museums, and lively tapas bars, Madrid offers a plethora of experiences for every traveler. As you wander through its streets, you'll discover a city that is as passionate about its past as it is about its future.
Portugal, with its picturesque landscapes and warm hospitality, is a destination that captivates the heart. Lisbon, the capital, is a city of contrasts, where ancient history meets contemporary culture. Porto, known for its port wine and stunning river views, offers a more laid-back vibe, perfect for leisurely exploration. Together, these destinations provide a comprehensive look at the Iberian Peninsula's unique charm.
Madrid at a Glance
- Best Sights: Prado Museum, Royal Palace, Retiro Park
- Must-Try Foods: Tapas, churros with chocolate, cocido madrileño
- Fun Fact: Madrid is home to the oldest restaurant in the world, Sobrino de Botín, established in 1725.
- Where to Stay: Explore accommodations on VRBO or Hotels.com
Days 1-5: Exploring Madrid
Begin your journey in Madrid, where you'll arrive in the afternoon. Spend your first evening enjoying a traditional Spanish dinner at Casa Lucio, famous for its huevos rotos. Over the next few days, immerse yourself in the city's rich culture and history. Visit the Prado Museum for a glimpse of masterpieces by Goya and Velázquez, and take a stroll through the lush Retiro Park.
For a unique experience, consider a day trip to Ávila and Segovia, where you can explore ancient Roman aqueducts and medieval walls. In the evenings, enjoy a flamenco show at Torres Bermejas or a tapas tour through the city's vibrant neighborhoods.

Lisbon at a Glance
- Best Sights: Belém Tower, Jerónimos Monastery, Alfama District
- Must-Try Foods: Pastéis de nata, bacalhau, bifana
- Fun Fact: Lisbon is one of the oldest cities in Western Europe, predating even Rome.
- Where to Stay: Explore accommodations on VRBO or Hotels.com
Days 6-10: Discovering Lisbon
Travel to Lisbon via train, a scenic journey that takes approximately 10 hours. Upon arrival, settle into your accommodation and enjoy a leisurely evening exploring the Alfama District, known for its narrow streets and traditional Fado music.
Spend your days visiting iconic landmarks such as the Belém Tower and Jerónimos Monastery. For a taste of local cuisine, join a food and wine tour to sample pastéis de nata and other Portuguese delicacies. Don't miss a sunset sailing tour on the Tagus River for breathtaking views of the city.

Porto at a Glance
- Best Sights: Ribeira District, Livraria Lello, Dom Luís I Bridge
- Must-Try Foods: Francesinha, tripas à moda do Porto, port wine
- Fun Fact: Porto is the birthplace of port wine, a fortified wine that is famous worldwide.
- Where to Stay: Explore accommodations on VRBO or Hotels.com
Days 11-15: Unwinding in Porto
Continue your journey to Porto, a city known for its stunning river views and rich wine culture. Travel by train, which takes around 3 hours from Lisbon. Upon arrival, explore the Ribeira District, a UNESCO World Heritage site, and enjoy a traditional meal at a riverside restaurant.
Visit the famous Livraria Lello, one of the most beautiful bookstores in the world, and take a stroll across the iconic Dom Luís I Bridge. For wine enthusiasts, a Douro Valley wine tour is a must, offering tastings and a scenic river cruise.

Days 16-20: Final Days in Portugal
Spend your final days in Portugal exploring the lesser-known gems of the region. Consider a day trip to the picturesque town of Sintra, known for its fairy-tale palaces and lush gardens. Alternatively, head to the Algarve for stunning beaches and dramatic cliffs.
As your journey comes to an end, take time to reflect on the incredible experiences and memories made. Enjoy a farewell dinner at a local favorite, such as A Cevicheria in Lisbon, known for its innovative seafood dishes.
As you prepare to depart, consider booking your return flight through Omio for the best options and prices.
This 20-day journey through Madrid and Portugal offers a perfect blend of culture, history, and relaxation. From the bustling streets of Madrid to the tranquil landscapes of Portugal, each destination provides a unique glimpse into the heart of the Iberian Peninsula. Safe travels!