Lisbon in May; day trip to Sintra, should we use a tour, a private guide or go on our own?

I did it myself - easy to get from Lisbon to Sintra by train. From the Sintra train station, you pick up bus 434 to take you up the hill to Pena Palace, which is what most people want to see.

The Pena Palace is colorful and beautiful from the outside. I didn't go inside - I've seen the inside of enough castles and palaces, personally, and didn't feel the need to see another one. I'll bet a guided tour would make an inside visit more informative, though.

The highlight of Sintra for me was the Quinta da Regaleira, which is down by the town not up on the hill. I highly recommend a visit.

Whether a guided tour would work best for you depends on our personal travel style. It's not usually something I do, but you might.

I did it as a cruise tour, so it included Cascais, which I quite enjoyed. Between the towns are cork forests. I believe if you had your own car or private tour, you could see about cork farm tours....if that interests you.

I’ve done Sintra both on a tour and by myself. I enjoyed the tour more because I didn’t have to navigate the throngs of tourists at the sites. Admittedly, it was also the first time so that might have had some bearing on my enjoyment.

My choices for a first timer would be Peña palace but just from the outside. The inside isn’t that great. Quinta de Reguleira for the grounds. Again, the inside of the house isn’t that great. And, if you have time, Montserrat. Both the grounds and the house are amazing.

And, respectfully to the other poster, the cork forests of Portugal are mostly in the Alentejo. The Sintra hills might have an ocasional Cork tree, but I’ve never see them. The forests are lovely but, unfortunately, have a lot of eucalyptus.
Incomem is an upscale restaurant in Sintra. These days, I use the reviews on Google maps and am always pleased and agree with the reviews.

We travelled via train to Sinatra by ourselves in November and it was easy. By choice we went to the Quinta da Regaleira and Castelo dos Mouros. Used grab to get around. Highly recommend both and travelling by your self.

We're headed to Portugal (and Spain) in May and will be day tripping to Sintra from Lisbon. We're doing it on our own, though a friend was there last summer and took a tour, which he enjoyed.

As far as lunch, in doing online research we came across a vlogger who does by the name of Max Nomad. He suggested two places, both of which we are considering: Sopa d'Avo and Tascantiga. You may also be familiar with the show Somebody Feed Phil, which streams on Netflix ~ for indulging your sweet tooth, Phil recommends Piriquitas, where he had both their travesseiros and queijadas.

Have safe and fun travels!

There is a lot to see in Sintra, so we took the train and spent the night so as not to be rushed.

Taking the train is pretty easy. There is a bus from the train station to Pena Palace, but we took Ubers to get around when we were there in late January. Regaleira is definitely worth a good chunk of time.