More than thirty years ago, my grandparents began spending a piece of winter on the island of St. Maarten and my own time there with them always felt particularly precious.
It was here that my grandfather and I would sit on the balcony, looking out at the ocean, and he would tell me stories about his childhood. Even in my twenties, I was enraptured as he recalled the kids he played stickball with in his Bronx neighborhood on the Grand Concourse and as he shared tidbits about his siblings and his time spent in the army. I can remember thinking that I needed to bring a recorder so that I could document all of the minor parts and players of this history. But I was always too in the moment to turn our sacred talks over breakfast by the beach into an interview.
My grandfather has passed and, as suspected, I sadly can’t remember most of the names of the friends and people of his nostalgia. But those cherished hours on the balcony feel so close and so clear. That those memories are indelible makes me grateful that I absorbed them with my heart and, for once, not with my pencil.
Today I am taking Sweetlips and The Bean to St. Maarten for the first time so that they may make memories of their own with their Great Grandmother who is returning each year still, even at ninety-one. It feels like a significant part of my life has come full circle. To know that I will see my two little boys standing on that same balcony each morning, my grandmother by their side retelling those life stories of her own, is as overwhelming as I fantasized it would be in my early twenties. Then, I was dreaming of a middle ground, grasping at my past as I embraced my future. Despite the passing of time and the shifting of generations, that part of me has still not changed. I like to think that to share with my children what was so personal and precious to me growing up might, in some small way, help them know their mom just a little bit better. And the story will then continue.
On a lighter note, it’s no secret that my grandmother (for whom, along with my grandfather, Garland Collection is named) has got serious style. Even on the beach, her look is elegant, timeless and oh-so-chic. Picture an emerald green and leopard one-piece with oversized Fendi sunglasses and tasteful gold jewelry — and you’ve pretty much got her signature island look. So while on this trip I will be schlepping a potty along with my Louboutins, I’ve made a packing list that I hope is worthy of hers.
Here are my go-to’s for making my chic grandma proud.
1. GARLAND COLLECTS VINTAGE EARRINGS 2. SWIMSUIT 3. SUNGLASSES 4. GARLAND COLLECTION GOLD LINK RING 5. SHOES 6. TOTE 7. TUNIC
UP CHIC'S CREEK 
As always: love, love, love.