The most expensive decision you’ll ever make isn’t the plane ticket… It’s deciding to stay where you are, and then wonder what could had been. It’s time to think about our moves for 2026, even if it’s only to plant the seeds. 

At this time last year, I announced my first group trip and was thinking… how delusional do I have to be to plan this entirely on my own? I rejected every trip planning platform that offered to work with me, because they could not live up to my standards. It wasn’t easy, but I ended up answering that question by selling it out and taking with me, the most amazing, brave, cerebral, diverse (and perhaps also a bit delusional) group of individuals who came together to spend a week with me in Greece, back in June. I cried multiple times during the trip just thinking about everyone’s journeys crossing into my own. 2025 has been a tough year for me, and it’s always in the tough times where we find the strength to break out of our cages and reap the rewards of our growth. I’ll never forget when Gina and I sobbed into each other’s arms in tears of pride and joy during our sailing trip, and this was right after my petit panic attack in the water. As Cancer girls do during Cancer season, of course. 

Right after that, I went island hopping and landed on the island of Ios, one of the most interesting islands in the Cyclades that perfectly straddles the chaos of becoming with the stillness of belonging. 

I hadn’t even heard of this island until I landed, and it gave me a paradoxical feeling that reflects my own views on life itself as a spectrum between everything and nothing. Tombs of literary legends amongst postcard-perfect traditional villages, pristine Mediterranean beaches, and sprawling art and nightlife venues. Getting lost in the narrow alleyways of Chora that lead you into wormholes of culinary magnificence and boiler room DJ sets, and yet somehow voted as one of the world’s top 100 hidden paradises (Hidden? Not really, with a nightlife reputation that can rival Ibiza, I’d call it up-and-coming. Criminally underrated and misunderstood? For sure.) On the island, there is a cliffside villa with an exotic garden and an infinity pool facing the Aegean Sea and mountains with some of the best views in Greece. Very quickly I made friends with the owners and then told them I’m bringing the loveliest group of people back with me next Summer. 

So, here I am. 

Here’s What Happened Last Time:

Thirteen people came for the pristine beaches in the midst of their own struggles, and left with something starkly different.

One angel told me while sitting by the water with the sun disappearing, “I came here thinking it would be a nice break. I had no idea how transformative this week would be.” Another said, “I arrived alone, and now I don’t want to go back.” And the one that got me was: “I didn’t realize how much more there is to life, to see and experience beauty in all of these different ways. I didn’t know it was even possible for me.”

And that’s actually where Ios lies… in it’s duality. Pristine cliffs that remind you of your smallness, and the energy of wild people that makes you remember that you too, belong to the earth. Water so clear and blue it feels like swimming through light. Evenings where the entire sky turns into colors that don’t have names. Late dinners and dance parties where strangers become your mirrors, when you see yourself differently because somebody else brings out a new and unknown side to you.

Transformation doesn’t just happen because of geography, but because of who you’re surrounded by and how intentional the space created is. Witnessing the conversations that start small and then grow into everything. Savoring the salt and thrill of turbulent, Iliad-worthy swells, eventually heading into still waters. The person who was seeking a journey to special destinations because they needed permission to slow down, and then left knowing how to command that permission.

This isn’t a typical vacation in the way you think of vacations. It’s really a container. A really intentional and beautiful container where you can actually do the work of remembering who you are outside of your daily life. Where you’re surrounded by humans doing the same work, which somehow makes your own inner work feel less lonely. It will be both quiet and wildly cathartic… and you’ll experience it for yourself.

Greece Summer 2026 Is Happening, July 2-8. We first land in Athens, then make our way to Ios the next morning, and finally, end our trip in Santorini. Everything else has been planned for you, all you have to do is buy your tickets. 

Next year, I want to return to Ios with you to play and dance in the waves til dawn. Maybe this time, I’ll muster up the courage to go cliffdiving. Then, we take in the breathtaking views of neighboring Santorini. Ios has become my favorite Greek island, but you have to see the otherworldly Santorini at least once in your lifetime. And let’s not forget the epic historic capital of Athens, where the scaffolding on the Parthenon has completely come down for the first time in two hundred years.

If you’ve been thinking about it, or if something in you just knew you needed this, the next five people who reserve a spot get $150 off on the deposit. Use code NEXTFIVE150OFF. I’m closing applications this month. 

Join me, not because it’s pretty (of course it is), but because you need to remember that you’re capable of getting outside your comfort zone. Come because you need to be around people who also fervently believe in their own evolution. Come because something in you knows you’re ready for more than the routine you’ve been accepting. You’re ready to live. 

Your rock bottom taught you how to rebuild. This trip will teach you that rebuilding can be light and joyful.

I’ll see you in Greece.