We picked up a rental car at the airport and headed out of Lisbon for a short drive to Sintra. I had been focused on the Pena National Palace and the village (which I thought was much closer to the Palace) but Annelise suggested a garden — the Gruta do Labirinto — which ended up being the most interesting place we visited in Sintra.
Because of the narrow streets and lots of traffic, the road system has been converted to a one-way system — it makes sense but takes a long time to go anywhere. If you miss a turn, it is 10 miles around the mountains to get back to the same point. The sites are spread out — we hired a Tuk Tuk to get us around on our initial visit to get acclimated, which included driving up about 1,500 feet in elevation.
Sintra was designated a UNESCO World Heritage Site in 1995 for its concentration of 19th-century Romantic architecture set within a unique cultural landscape. The Pena National Palace — the most visited monument in Portugal — was built by Ferdinand II of Saxe-Coburg and Gotha (consort of Queen Maria II) beginning in 1842 on the ruins of a medieval monastery. Ferdinand II planted trees from across the world in the surrounding park — today approximately 80% of the trees are non-native species, around 200 years old. The Gruta do Labirinto (also known as the Quinta da Regaleira) contains the famous Initiation Well — a 27-metre spiral descent into the earth, built for Masonic ceremonial purposes around 1910 and connected by an underground tunnel network. The Moorish Castle on the ridge above Sintra dates to the 8th–9th century AD.
The Gruta do Labirinto ended up being the most interesting place we visited in Sintra. The well was the highlight — now I know what the girl in "The Ring" saw.
The National Palace has a similar vibe to Neuschwanstein Castle in Germany — built in the 1800s by rulers who were literally trying to show off. One interesting thing he did was to plant trees from all over the world — so 80% of the trees are about 200 years old and non-native.
We stayed in a great AirBnB — but Sintra could have been a day trip on the train from Lisbon and if you are looking to avoid transitions that would be a good way to see the city. We had a nice dinner there — but no compelling reason to stay in Sintra instead of Lisbon.
Although you could find places to retire here — a bit touristy and limited public transportation options.
"Sintra could have been a day trip on the train from Lisbon. No compelling reason to stay in Sintra instead of Lisbon — but no regrets either."