Stop Overthinking Your Cycling Vacation

The best cycling vacation isn’t necessarily the hardest, fanciest, or most expensive one — it’s the one that fits you.

The way you like to ride. Travel. Recover. Explore. Eat. Spend your time off the bike.

I’ve done a few very different cycling trips over the years, and while they were all amazing, what made them enjoyable was that they matched what I wanted at that moment. Based on my fitness or training needs. Or a “must-see location. Or just some really compelling marketing that made me think “ooooh, I gotta see that!”

Choosing the right trip is less about finding the “best” one and more about narrowing down what kind of experience you actually want. Think of it as a process of elimination.

When I started writing this, it was giving instruction manual vibes, and I quickly realized I was building some sort of giant cycling-vacation decision tree. That isn’t the point, entirely. Choosing the right trip isn’t really about optimization — it’s about figuring out what excites you at that particular moment.

So instead, here’s my thought process for my most recent trip to Portugal.

I have a mental list of countries I want to visit. Portugal was pretty high on the list since I have been to Italy, France & Greece. It is in a “sort-of” order but I’m not tied to it if something pops up that gets me excited. Having a country in mind definitely helps guide things.

I started researching different Portugal cycling trip options. I wasn’t really sure what I wanted to see in Portugal so I was pretty open except I knew the coast was gorgeous so wanted that to be part of it for sure! I looked at some gravel trips, training camp trips, luxury trips and everything in between. The gravel sounded really interesting and I definitely considered it but what sealed the deal on the tours I chose was a combination of area covered and price. The cost allowed me to do TWO tours back to back, and therefore cover almost the entire coast! Also, the gravel tour seemed a little more “hardcore” and stayed in one general area. The thought of chillin’ as I rode the coast of Portugal sounded more appealing than “clinging to life and wheels”.

The pace of the tours was a bit more leisurely than I’m used to, and they used hybrid bikes as well, which I don’t usually ride. But basically everything else about the trip sounded perfect, so I booked it. My thought was “I don’t care, I can ride slower and it is vacation! I actually want to go slower and experience it!”

I realized I care a lot about where I’m riding, what I’m seeing and experiencing but I can be surprisingly flexible on pace, bike type, and even how “hard” the riding is if everything else feels right.

If I had been looking for a full-on training camp, this probably wouldn’t have been the right trip. But for a cycling vacation — where the goal is to see a place, not just suffer through it — it was perfect.

I embraced the casual pace, coffee stops and many, many scenic overlooks. There were actually opportunities to push a little in terms of effort and pace either on long flat stretches or on climbs, and I did. But that wasn’t the focus of the trip.

What matters to me on trips now generally is seeing as much as possible on a bike. The bike itself didn’t matter. Hitting xx miles each day or conquering epic climbs didn’t matter. Has it mattered before or will it on a future trip? Sure. And I’ll make sure that trip meets the needs of the moment.

That’s probably the biggest thing I’ve learned about cycling vacations: the “perfect” trip changes depending on what you need at the time. Sometimes you want a challenge. Sometimes you want adventure. Sometimes you just want pastries, ocean views and enough time to stop and enjoy them.

And honestly? All of those are valid.