I’ve been thinking lately about how rarely we get everyone we love in one place at the same time. Work schedules, kids’ games, the sheer logistics of adult life: it all conspires to keep us apart more than together, even when we don’t mean for it to. Somewhere along the way, togetherness stops being the default and becomes something you have to plan on purpose.
My sister and I have always loved traveling together. A few years ago, John and I planned a trip to Greece, and then life stepped in and we had to cancel. You know how it goes. Someone brings it up over dinner, everyone gets a little misty-eyed, and then the idea quietly gets shelved for another year. We did that more times than I’d like to admit.
So when we finally set real dates and half-jokingly invited my sister and her husband along, their yes came so fast it made me laugh (in the best way). I treated it like the small miracle it was.
Then the circle kept growing! John’s sister and her husband were going to be in Santorini around the same time so I adjusted our dates a bit to overlap, then two of our cousins joined us for a few days too. In-laws and lifelong family, all saying yes to the same sun-washed days in Greece.
There's something different about traveling with the women who have known you your whole life. My sister and I finish each other's sentences the way you only can after decades of shared history; the inside jokes that need no explanation, the ability to read a mood across a room without a word. AND, we were very lucky that our husbands were friends as well. And since I dated my husband since high school, his sister has been “my sister” for more years than not. What we love about traveling with them is the ease, the independence and the evenings watching sunsets, wine and laughing. We have our own rhythm, our own shorthand. That's the part of this trip I didn't plan for and cherish the most.
I share all of this not because a sister trip to Greece needs to look exactly like ours, but because I want to encourage you toward whatever version of this belongs to you. The people who feel like home, wherever in the world you take them.
Below, I'll walk you through what the trip actually looked like, cobblestones, sandals, and all.
P.S. If cobblestones are involved, and in Greece they always are, pack the sturdy sandals before you go … or buy the most amazing pair there. Trust me on this one.
A quick planning reminder: VIP Travel Experience will be temporarily closing to new trip planning requests from November 30 through January 4 as our team takes time to finalize upcoming journeys and prepare for the year ahead. If you've been dreaming about a trip of your own, now is a wonderful time to get the planning started!
Cobblestones Will Humble You
Nobody warns you enough about Greek cobblestones and steps of Oia. They're beautiful, worn smooth by centuries of feet before yours, and they will absolutely wreck a pair of the wrong shoes. My sister learned this the hard way about two days into Santorini, hobbling through Oia in sandals that were gorgeous and entirely wrong for the terrain.
So we did what sisters do; we found a little shop tucked off the main path and she walked out with the perfect pair of walking sandals, sturdy enough for the whitewashed steps and stylish enough that she wore them the rest of the trip.
It became a running joke between us for the rest of the week, but it also became one of my favorite memories. Not because sandals are inherently memorable, but because that's travel with people you love; the practical becomes personal, and the small moments end up being the ones you talk about years later.
Where Ancient Meets Everyday
Greece has a way of making history feel close instead of distant. We wandered through Athens with the Acropolis rising above us like it had never left, then found ourselves days later on a boat drifting past caldera cliffs in Santorini, the water somehow bluer than any photo can capture.
We ate slow, sun-warmed lunches of grilled octopus and tomatoes that tasted like they'd been picked an hour earlier, because they probably had. Evenings meant watching the sky turn colors over the Aegean while the four of us argued good-naturedly about where to eat dinner, which, honestly, might be my favorite kind of argument to have.
What I'd Want You To Know
If you're picturing a trip like this for the people in your own life, whether that's a sister, a mother, lifelong friends, or family you've gained along the way, my honest encouragement is to stop waiting for the "right" time. There isn't one. There's just the decision to go.
What I will tell you, from firsthand experience, is that comfortable shoes matter more than you'd think, the best moments rarely show up when you’re checking things off of a list, and traveling somewhere ancient with people who feel like home has a way of making you savor your own life a little more once you're back in it.
I'm so grateful I got to experience Greece the way I did; surrounded by family, laughing over sandals and sunsets, and coming home with a closeness that felt even stronger than when we left.
If a trip like this has been living quietly on your someday list, I'd love to help you plan the version that's right for you and the people you'd want beside you.