One of the main drawbacks of traveling solo is if you want pictures, you have to get out of your shell and ask others to do it. It’s even worth it to get friendly with a person you don’t particularly enjoy, if only to dutifully take each other’s photos. This is the story of when I went to the storybook town of Sintra and overcame my fear of asking strangers to take pictures of me.

I departed for the train station in the balmy, sunny weather and it took me to look up from my phone to notice the sky turned cloudy. Fog, I learned, is another similarity that Lisbon shares with my hometown of San Francisco. It was then that I realized that not only had I failed to check the weather, I had no plan of what to do. No idea what I was supposed to see. No idea how to get there. Did I just forget how to travel?

Emerging with the other train passengers, a guide politely told me that hiring a private tuk-tuk for just myself would be out of my budget. “Are you cold?” he asked, seeing me shiver in the overcast weather. He suggested I buy a fleece from the souvenir shop just across the street. “There’s also a local goods shop here,” he said, pointing to Cabo da Roca.

Cabo da Roca

Cabo da Roca is not a castle, or ruins, but rather a jagged coastline marking the westernmost point of continental Europe. The first stop on the hop-on hop-off bus was Quinta de Regaleira, a former palace, but I skipped it. Being so close to town, there’s usually a long wait to get in and I could not survive the wait outside.

Kid’s sweatshirts ten sizes too small and handmade knitted sweaters three times what I could afford were what I found at the Cabo da Roca giftship. So instead of clothes I ordered aguardiente, a clear, strong liquor that had so far been a great addition to coffee. As I warmed up, I congratulated myself on my thinking overlooking the fact that I’d soon be walking across rocky cliffs.

My fears were assuaged by finding a couple of travelers – one from Russia, one from China – who took turns taking each other’s photos. I give this photo a 2 out of 5, with points for the beautiful backdrop and my dress that while not functional was doing work in the coastal breeze. But zero points for the subject (me!). Even though I made new friends here, wind is usually not your friend nor is overhead lighting.

Castelo dos Mouros

The hop-on hop-off bus takes a one-way circuit, so you need to know your stops ahead of time because there’s no backtracking. The rest of the day was warmer, and I managed to fit in the medieval Castelo dos Mouros as the sun burned off the clouds midday.

This was taken by a fellow solo traveler who had a DSLR camera on them. You can tell the quality of the framing but I really hate that I look like I was going to a sunny Mediterranean beach, not medieval castle ruins.

This is when I ambushed another photographer on another stretch of the wall. Why is my arm like that? I can feel the texture of the stone parapets on my arm as I type. Why this pose, you ask? I couldn’t say.

Palacio de Pena

Palacio de Pena stuns with its bright, candy-colored ornamentation. Feeling inspired, and confident, I asked three different strangers to take a picture as I wandered around.

Points to this couple who did try to avoid people walking into the background. The lighting must be diffused here, flattering the subject.

The walkway up to the Palacio is a shot where you should arrive at 9 am when nobody’s around, also to avoid literally standing in its shadow. I had stopped this photographer as they were on their way up, so I don’t blame them for only taking just this one photo.

Point taken off because of my hair. While the wind calmed down during the day, it returned for a last hurrah.

Getting back to the Sintra train station was comparatively hectic, the wait made worse (for me) by the onset of wind and night. Everybody wanted to get on the shuttle at the same time, and I realized that it was good that I had listened to the guide earlier and bought the more expensive hop-on hop-off ticket, which allowed me to squeeze onto any of the buses that passed the last stop.

What would I have different? I would have brought warmer clothes and maybe worn my hair in a bun. But I don’t regret not having a plan because in the end it all worked out.

As quickly as I had arrived, I departed Sintra back to Lisbon. It was still sunny when I returned.