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Six days of island hopping, barefoot dinners, poolside afternoons, and the kind of joy that's easy to forget as an adult. Creativity, connection, and a reminder that life is meant to be enjoyed.
Tolu, colombia
June 2026
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Six days spent lingering over meals, wandering through vineyards, creating beautiful things, and remembering that life is meant to be tasted, not rushed through.
Douro Valley, portugal
march 2026
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Six days of ocean views, meaningful conversation, Caribbean sunsets, and the kind of friendships that make you feel instantly at home. A week dedicated to connection, community, and belonging.
SoufriEre, saint lucia
December 2025
"It healed something in me that I didn't know needed healing. Through being in the company of so many amazing women I found myself again. How Alyssa managed to do all that in one week, I will never know, but I am forever grateful."
"There is something so freeing about not having to plan anything at all. Everything is taken care of and all you have to do is show up and be present."
"If you want to experience belly laughing at the kitchen table until 6am, Pillars is the experience for you."
"Alyssa is like your second mom. You can tell how much intention and love goes into every part of the experience."
