5-Day Lisbon and Madrid Adventure Itinerary

Today, embark on a guided day tour of Sintra, Pena, Regaleira & Cascais, which includes a visit to the enchanting Sintra, the colorful Pena National Palace (Palacio Nacional da Pena), and the mystical Quinta da Regaleira E-Ticket & Optional Audio Guide.

Enjoy a leisurely lunch at Taberna da Rua das Flores, a cozy restaurant known for its traditional Portuguese dishes. Afterward, explore the beautiful coastal town of Cascais and take in the stunning views of the Atlantic Ocean.

Return to Lisbon and relax with a sunset cruise on the Tagus River with a welcome drink, taking in the city's iconic landmarks from the water. For dinner, indulge in a gourmet experience at Feitoria Restaurant & Wine Bar, known for its innovative cuisine and extensive wine selection.

Begin your day with a visit to the Commerce Square (Praça do Comércio), one of the grandest squares in Lisbon. Then, explore the historic Lisbon Cathedral (Sé de Lisboa) and the impressive National Pantheon of Santa Engracia (Santa Egracia Panteao Nacional Lisbon).

For lunch, head to Cervejaria Ramiro, a famous seafood restaurant loved by locals and visitors alike. Afterward, take a guided walking tour of Lisbon's history, stories, and lifestyle, with food tasting and drinks included, to gain a deeper understanding of the city's culture.

In the evening, experience the vibrant nightlife of Lisbon at the iconic Bairro Alto. Enjoy a dinner at Bairro do Avillez, a trendy restaurant offering a modern twist on Portuguese cuisine, followed by drinks at one of the lively bars in the area.

After traveling from Lisbon to Madrid, start your day with a Spanish breakfast at a local cafe. Then, visit the world-renowned Prado Museum (Museo del Prado) to admire its impressive collection of European art, including works by Goya, Velázquez, and El Greco.

For lunch, try the traditional Spanish dish, paella, at Mercado de San Miguel, a popular food market in Madrid. Afterward, take a leisurely stroll through the beautiful Retiro Park (Parque del Retiro), where you can relax by the lake and visit the Crystal Palace.

In the evening, explore the vibrant neighborhood of Chueca, known for its lively atmosphere and diverse dining options. Enjoy a delicious dinner at DiverXO, a Michelin-starred restaurant offering innovative cuisine, followed by a nightcap at a trendy cocktail bar.

Today, take a day trip from Madrid to the historic city of Toledo, known for its rich cultural heritage and medieval architecture. Explore the city's iconic landmarks, including the Toledo Cathedral (Catedral Primada) and the Alcázar of Toledo (Alcázar de Toledo).

Enjoy a traditional Spanish lunch at Adolfo, a renowned restaurant in Toledo known for its regional cuisine. Afterward, visit the Santa María la Blanca, a former synagogue that showcases the city's multicultural history.

Return to Madrid and spend your final evening in the city at Malasaña, a hip neighborhood known for its vibrant nightlife. Explore the area's eclectic bars and restaurants, and savor a farewell dinner at La Tasquita de Enfrente, a popular local eatery.