That Cerulean Blue
FROM THE ROAD | Founder’s Dispatch
by Tina
A week sailing the Cyclades, eight friends, and the birthday that made me understand what I wanted to spend my life doing.
The mornings were the best part. We’d dock the night before at whatever marina the captain had chosen, and by early morning the world was still and quiet — just the sparse ambient sounds of the day beginning on the docks. It reminded me of the feeling you get when you unzip your tent on a camping trip. Sleep still in your eyes, the natural environment right outside your door, the world not yet asking anything of you. Except instead of trees, you climbed out to the sight of a Greek sunrise hitting the white and blue architecture of the islands, the light doing things to the color of the hills that I don’t have words for. Like a painting. We’d drink our coffee in silence, just watching. There was nothing else we’d rather do.
That was the rhythm of the week. Unhurried, sensory, completely present. Once we found our sea legs (more on that shortly) the rocking of the boat became its own kind of soothing. The Aegean has a way of rearranging your priorities. After a couple of days, whatever had felt urgent before simply stopped mattering.
I’ve been the planner in my friend group for as long as I can remember. It’s not a role I was assigned; it’s just who I am. I have a genuine curiosity about destinations, and I approach a trip plan the way you’d approach a gift for someone you love. The research, the curation, the care about getting it right — that’s not a burden. That’s the point. I want to give people joy and a cherished memory. I always have.
Greece draws me in like a magnet. The alchemy of all its parts speaks to something in me spiritually. I’ve traveled there a few times and I’ll keep going back. The food is extraordinary, built on flavors honed over centuries. The people are warm and hospitable in the way of people who genuinely want you to love where they’re from — show the right appetite and they’ll steer you toward their favorite dishes, send out a round or two of ouzo, make sure you understand what you’re tasting and why it matters. Even the simplest plate carries that history. And then there’s the Mediterranean sun, which hits differently than anywhere else I’ve been. It warms you from the inside out.
Cerulean to azure to turquoise — all clear as crystal
Then there’s the water. That cerulean blue. It was my favorite crayon as a kid, and seeing it for real, as far as the eye can see in every direction, is genuinely otherworldly. A feast for the eyes that doesn’t get old no matter how long you sit with it.
For my 40th birthday, I’d been dreaming of a sailing trip for years. Greece felt right. I found a catamaran, invited my friends, and planned it the way I plan everything: with care, with curiosity, and with a lot of love for the details.
The trip was originally supposed to take us through the Saronic Islands, closer to the mainland. But the morning we embarked, our captain, who was 26 years old, with the seamanship of someone twice his age, told us that conditions were exceptional. A rare window. We could sail farther, out to the Cyclades, if we were willing. We were willing.
Five hours into that first sail, half the boat was seasick. Myself included. I remember standing at the stern, starboard side, facing what was genuinely one of the most perfect sunsets I’ve ever seen — pink and purple bleeding into the horizon — and being sick over the side of the boat. The wind, mercifully, was working in my favor. There’s something oddly liberating about that moment. The ocean has no interest in your dignity, and once you stop fighting it, you’re free. We laughed about it for the rest of the trip. Still do.
Once we had our sea legs, everything opened up. Our captain would anchor us somewhere beautiful for breakfast — a quiet cove, a harbor just waking up — and we’d swim before we ate, then eat, then swim again. Then sail somewhere new for lunch. Each island different from the last. Each anchorage its own small discovery.
As destiny would have it, on the day of my birthday, our captain caught a massive tuna off the back of the boat. It was an event. He battled to reel it in, visibly proud, excited to do something special for us. He prepped it immediately. Fresh poké, right there on the boat, and it was the best tuna any of us had ever tasted.
But my favorite moments of the whole week were simpler than that. Sitting on the bow as we sailed, a cold drink in hand, the wind on my face and the sea stretching out in every direction. Drinking while surrounded by water is typically a special occasion. On this trip, it was just Tuesday. We’d float in the water with our drinks and soak up the sun, or perch on the bow and watch the islands go by, talking the way you only talk when you’ve been properly unplugged for days. The conversations that require the right remove from ordinary life.
I want to say something about the cost, because “private sailing catamaran in the Greek Islands” can sound like a certain kind of trip for a certain kind of person. It doesn’t have to be. Split eight ways, the week came to roughly €2,000 per person for seven nights aboard, a captain, a cook, and more islands than we could fully absorb (technically, the vessel could have carried four more people, which would have reduced the cost for each person even further). Per night, that’s less than a hotel room in Santorini. Part of what I do now is find exactly this kind of thing: the experience that sounds out of reach and turns out to be entirely possible, if you know where to look and how to structure it.
That’s really where The World Travelist came from. Not from a business plan, but from years of planning trips that bonded people, that gave them stories they’re still telling, that showed them something about the world and about themselves. The Cyclades trip solidified something I already knew: that a trip planned with genuine care can exceed what anyone thought was possible. I came home wanting to do that for other people. I still do.
A year and a half later, my friends still talk about that week. The water. The mornings. The conversations. The meals. The serenity. The sunsets. And did I mention the water? The feeling, somewhere around day three, that real life had become a total dream.
That feeling is what I’m in the business of creating.
If there’s a trip you’ve been turning over in your mind — a birthday, an anniversary, a week you’ve been promising yourself — I’d love to help you plan it.
More where that came from.
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