Portugal and I have history.
Not the tourist kind. Not the “took a river cruise and loved the pastéis de nata” kind. I mean I just keep coming back, the way you return to a place that keeps showing you something new. Slow mornings in Lisbon cafés where nobody is in a hurry because the Portuguese have correctly decided that mornings shouldn’t be hurried. Lining up with locals for bifanas at Casa das Bifanas. Hiking the Levada trails in Madeira with legs that protested the whole way down and didn’t regret a single step. The afternoon light hitting the azulejos in Évora around 4 p.m., the way it catches the blue and white tile and turns the whole street into something you want to stand there and soak in. Standing at Cabo da Roca watching the Atlantic come in, that westernmost point of continental Europe, thinking what everyone thinks when they stand there: that there’s something about standing at the edge of a continent that resets you.
I travel to Portugal the way I travel everywhere: independently. My itinerary, my pace, my decisions. The freedom to follow an unfamiliar alley simply because I could. Color-coded spreadsheets I’d built and the freedom to abandon them when something better appeared. I am, in case this isn’t already obvious, a planner who also loves to be surprised. That combination works very well when you’re the one holding the clipboard.
But… I’m going on a group tour.
I know. Take a second. It’s actually making my heart beat a little erratically too.
Here’s how this happened. I’m a travel advisor. I recommend group tours to certain clients all the time. I can evaluate an itinerary, assess a tour operator, read a packing list. What I have never done, though, is sit in the seat. I don’t actually know what it feels like to hand the clipboard to someone else, to be carried through a place by a guide I’ve never met, on a schedule I didn’t build, with people I haven’t chosen. That gap started to bother me — and then I spent some time asking clients who’d done group tours what they actually thought of the experience, and the answers made it worse. I expected: “It was fine. Better than planning it ourselves.” I got: capital-L loved. And when I pressed them on why, I got answers I didn’t expect. The stories I heard had a theme: a guide who knew the back entrance, an hour somewhere that wasn’t on the public schedule, access that simply wasn’t available to anyone booking independently. And more than once, someone mentioned the people. Strangers on day one, friends by the end. People who actually travel together now.
I arrange group tours for clients and I know what makes a group tour worth recommending. What I’m realizing is that I’ve been evaluating a product without understanding the experience of it. Those are different things.
So in a few days, I’m flying to Portugal with Collette. Ten days across a country I know, through someone else’s lens.
I would be lying if I said I wasn’t skeptical.
Here is what I’m skeptical of: pacing designed for the median traveler, which is rarely my pace. Stops at shops I didn’t choose and don’t want to enter. The moment when the group dynamic works against you, when someone is slow or someone has a question the guide has clearly answered seventeen times already and you are standing in the sun waiting. The feeling of being moved through a place rather than moving through it yourself. These are the things my independent-traveler self keeps bringing up, the way a skeptical friend keeps asking “but are you sure?” when you’ve already bought the ticket.
Here is what I’m curious about: the access. The guide who knows the back entrance. The thing you don’t find on your own because you don’t know it exists and it doesn’t have a website. And the people. I want to see that for myself.
I’ve given myself extra day at the start to explore Porto on my own before the group meets. It feels necessary. I’ll arrive, walk along the Ribeira, find a café by the river with a glass of vinho verde, and just be in the place before shifting into shared travel. That day is mine. Then I hand the reins over.
I’m curious whether I’ll notice the moment the dynamic changes. Whether it’ll feel like relief or like something else.
The Collette itinerary covers Portugal top to bottom: Porto, the Douro Valley, Coimbra, Lisbon, Évora, the Algarve, Sagres. Some of those places feel like old friends. Others I’ve only seen from a car or train window, passed through on the way to somewhere I was going on my own schedule. Normally when I look at an itinerary I’m looking for what’s missing, what could be swapped, where the pacing feels off. This time I’m trying to look at it as a traveler. The wind off the cliffs at Sagres. The particular quiet of Évora’s cathedral square on a weekday morning. A Douro Valley vineyard at dusk, which I’ve had on my radar but not yet visited. I want to see what Collette sees in these places. I want to understand what a good tour director does with the same material I’ve been working with independently.
There’s a strange thing that happens when you travel somewhere you already know well. Part of you relaxes into the familiar. Part of you is constantly comparing the current experience to the one you remember. I’m curious how those two things will interact when I’m not the one driving the day.
I’m also thinking about what this means for the clients I work with. Some of them are independent travelers who’d hand me this piece and say “exactly, this is exactly why I’d never do a group tour.” But some of them aren’t. Some of them are people who find the planning genuinely overwhelming, who light up when I tell them someone else will handle it, who actually want to be in a group because a group means built-in company and a human buffer against the unexpected. Those clients I’ve been serving with information rather than experience. That’s the gap I want to close.
And more quietly: I want to know what it feels like to just show up. Because that’s what my clients do every time they trust me with a trip. They show up. The work is already done. I’ve never experienced that from the inside, and I think it matters that I do.
My suitcase is half-packed. Camera, notebook, the lightweight scarf that lives in my carry-on permanently because there’s always a sudden breeze somewhere. I’ve packed comfortable shoes and what I’m calling deliberately low expectations, which is either good practice for an experiment or just the kind of thing you say to yourself before you try something new.
If Portugal is calling your name, or you’re curious whether a group tour might be the right fit for your next trip, I’d love to talk. Let’s chat.
