I think our favorite day for the most unexpected adventure in Portugal was our our visit to Sintra.

When I thought about a day trip to this UNESCO World Heritage area from Lisbon, I expected to take a train ride and then spend the day hoofing it from castle to castle. I hoped for good weather, but at this point in our trip, that was kind of iffy.

We had a couple of credits on Airbnb due to pandemic trip cancellations, as well as a gift certificate (which, by the way, is a FANTASTIC gift idea for the person who has everything and likes to travel), so we splurged on a Jeep safari.

The day started with a near disaster as our driver stopped to pick us up in front of our building in the middle of the busy Rua da Prata in rush hour, then gestured at us to jump in the car as the approaching traffic collectively slammed on their brakes.

At this point half of my freaking family (in particular, the two I would have expected to know better) darted across the road while all I could manage was to squeak out “bus!” by way of warning.

It was actually a bus, a street car, a couple of taxies and a bicycle messenger who had a few, choice words for our driver. But we all lived and made it to Sintra where our guide, Diogo, picked us up in his rig to show us around.

I’m as down for a castle tour as the next person. But I also know that a day of standing in lines to traipse through large, dark, old spaces with lots of stairs, to marvel at someone’s silver collection and frescos can get old really quickly for our crew. I didn’t have high expectations for this day, but after a near death experience, figured things could only get better.

Our “Jeep” was actually a vintage Portuguese off-road UMM (União Metalo Mecânica). It’s a rare French-designed truck manufactured from the late-70s until mid-90s, which has quite the cult following in this region.

… which is when I realized the emphasis on this Sintra experience might be less “castle” than I’d given it credit.

First, we visited the manor and grounds of the Quinta da Regaleira, built in the early 1900s by collector and Freemason António Augusto Carvalho Monteiro (also known as “Monteiro the Millionaire”). It’s just up the block from the Quinta do Relogio that Madonna purportedly bought in 2017 for 7.5 million euros; a tree-obscured building with Moorish-looking arches which Diogo pointed out with a half-hearted wave.

Maybe not a big Madonna fan, our Diogo.

Madonna’s place dates back to the 18th century, designed and buil in a neo-arabic style, and is a current UNESCO World Heritage site of its own. From what I could see it didn’t look like she has made much headway in refurbishing it. Diogo told us her initial plans have been rebuffed by local officials.

I can’t imagine even Madonna having it any easier with remodeling a UNESCO site than anyone else, but she’s purportedly living in a spacious and already remodeled Lisbon castle in the meantime with all her kids, so maybe she’s not in a hurry.

Diogo dropped us off at the Quinta da Regaleira and told us to look for signs of the Knights Templar in the estate chapel and the manor, and to take our time exploring the initiation well, the one of two such wells on the estate – the only one open to tourists – with tunnels branching out from the bottom that lead to hidden lakes and grottos crowded with baby boomers clogging up the pedestrian traffic posing for backlit photos.

From there, we made our way to the village Diogo grew up in, where we saw the vineyards and had lunch at one of the two restaurants in town. The restaurant is family owned and decorated by the paintings made by the owner. While our vehicle was one of several on the tour that day, we were the only tourists at this establishment. Diogo said the guides have the ability to pick and choose between routes, and said they’re encouraged not to congregate all in one restaurant lest the locals get ticked when they can’t find a table. The menu was all in Portuguese and Diogo made recommendations.

On the way there, we checked out a vineyard of particular interest for the wine world in general. The Colares region located near Sintra is the second oldest demarcated wine region in Portugal after the Douro and one of the world’s oldest producing areas in general. When a mid-1800s aphid infestation nearly destroyed every single wine grape in the world, wineries all over Europe ripped up and burned their family’s ancient vineyards in a desperate attempt to stop the spread. It didn’t work and by the 1900s there was an international wine deficit. Over 70% of the vines in France in particular were dead.

The Colares region grapes were safe from the scourge. Grown in to be hearty in strong costal winds and in sandy soil where the roots grow meters deep to reach water, they’re one of the few grape stocks that survived the infestation.

Which is how we were able to taste a wine with our lunch that in all honesty was wasted on our inexperienced palates in particular.

But we appreciated the sentiment.

From there, we headed to the coast, while Diogo blasted 80s pop music. The weather was perfect for a drive.

After a little nip of port at the westernmost point in Europe, Cabo da Roca, our trip concluded in the resort town of Cascais. With its Laguna Beach vibes, it’s definitely where the rich and famous come to play while in Portugal.

From there it was an easy light rail train ride back to Lisbon.

Later, we all agreed that this was probably our best overall day in Portugal, with amazing weather and the perfect ratio of castles to rare wine tasting to near misses by buses.