My favorite trip to Sintra was the one in which I did a tour. With a tour, I didn't have to deal with buses or Ubers, or try to determine where to go, etc. I had plenty of time to explore the places we visited, too. I, personally, don't think the inside of Peña is worth the time or fighting the crowds.

A guided tour of Sintra is highly recommended because the region’s primary attractions—Pena Palace, Quinta da Regaleira, and the Moorish Castle—are spread across steep, forested hills that are notoriously difficult to navigate independently. Sintra’s narrow, one-way roads are often congested with traffic, making driving stressful and parking nearly impossible. While public buses exist, they are frequently overcrowded, leading to long wait times. A professional guide provides seamless logistics, managing all transportation and ensuring you hit the strictly timed entry slots for Pena Palace. Beyond the logistics, a guide enriches the experience by explaining the complex Manueline and Romanticist architecture and the esoteric symbolism within Quinta da Regaleira’s initiation wells. Many tours also include stops at Cabo da Roca, the westernmost point of mainland Europe, and the coastal town of Cascais, offering a comprehensive and stress-free "best of" itinerary that is difficult to replicate on your own.