There is a specific type of travel guilt that hits when you’re in a beautiful destination and you haven’t “conquered” a mountain yet. You see the photos on Instagram: a hiker standing silhouetted against a lilac sky, looking reflective and remarkably un-sweaty.
Last month in Madeira, Portugal, I decided I wanted that silhouette. I wanted to be the person who “communes with the peaks.”
Spoiler alert: The peaks did not want to commune with me.
The Expectations vs. Reality of Solo Hiking
I picked a trail that the guidebook described as “moderate” and “rewarding.” In my head, I was a protagonist in a cinematic adventure. In reality, I was a person in brand-new sneakers who had forgotten how much I actually dislike the feeling of my own heart rate increasing.
The Ascent of Regret
About twenty minutes in, the “moderate” incline began to feel like a personal insult.
- The Struggle: I was passed by a family of four, including a toddler who was literally skipping.
- The Social Anxiety: Every time a hiker coming from the opposite direction said “Bom dia,” I had to decide if I had enough oxygen to reply or if I should just give a ghostly, non-committal thumbs up.
- The Gear Fail: I realized I had packed two liters of water but zero snacks. I was essentially a human hydration bladder with no fuel.
3 Lessons for the “Accidental” Hiker
If you find yourself pressured into a “must-do” hike, keep these things in mind to avoid a total meltdown:
- The 30-Minute Rule: If you aren’t enjoying yourself after 30 minutes, you are allowed to turn around. The mountain won’t tell anyone.
- Check the Descent Time: “Sunset” hikes are beautiful until you realize you have to walk back down in the pitch black. Always carry a headlamp, not just your phone flashlight.
- Download Offline Maps: Apps like AllTrails are lifesavers when the trail markers suddenly become “interpretive.”
The Summit Stand-Off
I eventually reached the viewpoint. The sky was, admittedly, spectacular. It was a bruised purple and gold that made everything look like a Renaissance painting.
I took out my phone to capture the “moment.” I tried to look reflective. I tried to look like I belonged there. But then, a large, aggressive mountain bird (a chaffinch with no fear) landed on my backpack, looking for the snacks I didn’t bring. I shrieked, tripped over a rock, and nearly took out a tripod belonging to a professional photographer.
Why We Should Embrace the “Failed” Adventure
I didn’t get the perfect silhouette. I got a photo of my own panicked hand and a blurry bird wing.
But as I limped back down to the village to find the largest plate of espada and bananas available, I realized something important. Travel isn’t about becoming a version of yourself that likes hiking. It’s about discovering that you’re the version of yourself who likes the idea of a hike, but prefers the reality of a wine bar at sea level.
There is no “wrong” way to see the world—even if you see most of it while catching your breath on a rock.