Explore the winding streets of Alfama, Lisbon's oldest district. Visit Castelo de Sao Jorge for breathtaking views of the city and then head down to the famous Praça do Comércio to soak in the architecture and atmosphere of this picturesque city square.
Explore the fairytale castles and lush forests of Sintra. Visit the iconic Pena Palace, a colorful and eclectic palace perched atop a hill. Walk through the mystical gardens of the Quinta da Regaleira, complete with hidden tunnels and a famous inverted tower.
Take a step back in time to explore the medieval walled city of Toledo. Visit the stunning Catedral Primada and the ancient Santa María la Blanca Synagogue. Take a walk along the city walls for a breathtaking view of Toledo's winding streets and hilltop castle.
Experience the bustling city of Madrid. Visit the famous Prado Museum to view famous works by artists such as Velázquez and Goya. Take a stroll through the lush Parque del Retiro and then head to the vibrant Puerta del Sol for some shopping and people watching.
Visit the picturesque town of Segovia, famous for its charming medieval streets and ancient Roman aqueduct. Explore the impressive Alcázar, a towering castle that looks straight out of a fairytale. End your trip with a stroll along the scenic Eresma River.
If you have more time, consider visiting the beautiful beaches and coastal towns along Portugal's Algarve region. Or, explore Madrid's bustling nightlife scene by visiting local bars and clubs. If you have less time, consider skipping Sintra or Segovia to spend more time in either Lisbon or Madrid.