Ok, it's WAY too short of time - but we will be picked up at the cruise port in Lisbon at 2:00 p.m. on an early weekday June afternoon - and have arranged about 5 hours with this driver. The plan is to go to Sintra and see what we can outside of Lisbon before we are dropped back in the Alfama area. We have until 2:00 p.m. the next day to explore Lisbon itself. So - if we can see only ONE big site in Sintra, which should it be? We're thinking it will be enough to see Pena from the outside, and we'll have to choose between Moorish Castle and Quinta da Regaleira. Which is going to be harder to get to and more crowded in the afternoon? We've heard Cabo de Roca, Azenhas do Mar, and Cascais are all worth a look on the way back but if we only have time for one?????????? Logistics as well as highlights matter.

I think you got it right but only If you can't do both fanciful Pena Palace and walk the old walls of the Moorish castle - I enjoyed both but walking the old ramparts on the Moorish Castle was great.

Go for Quinta da Regaleira. We have been to many, many castles and palaces. After a while, many become a blur. But Quinta's gardens, tunnels and eccentric stuff will always provide fond memories. It's been a while, maybe 8 or 10 years and it was in the fall, but we had the place to ourselves.

I vote for Quinta da Regaleira. Really enjoyed roaming the grounds and tunnels....very different than anything we have ever seen.

Another vote for Quinta da Regaleira. Monserrate is also worth a visit.