Redefining The Holidays With A Grand Cayman Getaway
- Katherine Rose Woller
- 3 hours ago
- 7 min read
When I think of a winter holiday away, I do not dream of palm trees. I picture colder temps, cozy fireplaces, and fair isle sweaters paired with fuzzy socks. So, when my mom told me that we were going to Grand Cayman this year for Christmas, I was dubious. Sure, it does sound like a perfect sunny Spring Break getaway, and one that I would happily embark on again as the weather warms in the coming months, but a magical Christmas celebration? Not so much.
Where would our moments of togetherness stem from if we weren’t all forced to take shelter from the cold, dark of winter? What about my hot chocolate dreams and cozy fireplace wishes? How does one create that vibe on a Bahamian beach?
Don’t get me wrong, I was thrilled to warm my pregnant belly in the Caribbean sun, but I wondered if it could create the same feeling of a connected family holiday that I craved.
For the first time in roughly six years, the whole crew was on board for the sojourn south, which was momentous in and of itself, given the schedules of four sisters. Still cautiously optimistic, my husband, our daughter, and I made the full-day trek to Grand Cayman and wearily settled into our shared family digs at Black Urchin Boutique Resort.
Determined to orient ourselves slowly on the first day of vacation rather than jump headfirst into activities and the chaotic mental stress of trying to fit it all in before nap time, I unpacked. At the same time, Rose set off on an adventure with one of my sisters and her partner. They walked the beach making sand castles, playing in the waves, and hunting for seashells, which she proudly showed off upon her return.
We spent the afternoon immersed in impromptu swim lessons before setting off for a much-needed, adults-only dinner on the expansive outdoor terrace at Grand Old House.
An enticing Armagnac Library briefly detoured us with shelf after shelf of decadent French brandy, the oldest of which dated back all the way to 1893. Once everyone was seated, I snacked away on an ice-cold Hamachi crudo with tangy yuzu dressing and the perfect kick from fried jalapenos. The hectic travel energy finally settled.
The necessary ordering shenanigans ensued. As my beautifully aromatic seafood curry, piled high with an abundance of lobster, shrimp, mussels, fish, and freshly plucked mango chutney arrived, we immediately launched into an extended discussion (read debate) about everyone’s top three to five favorite movies of all time.
Titles ranged from Scarface to The Hangover, and my own contributions of A River Runs Through It, Bull Durham, and the
Pierce Brosnan version of The Thomas Crown Affair rounded out a cinematic roundup that was as diverse as the personalities surrounding me.
The dessert for us was a rapid-fire run-through of answering the shockingly difficult question:
“If you could go to any concert from the past, what would it be?”
The 1985 Live Aid Benefit concert at Wembley Stadium featuring Queen’s iconic set. Lady Gaga at Madison Square Garden. The 1969 Rolling Stones concert in Hyde Park. Elvis, in general, though my mom saw him live.
All in all, it was fascinating not only to see the generational differences that emerged, but also to discern how each person’s responses mirrored their unique personality and tastes. None of it was shocking per se, but it all reflected the people I love so dearly. It was also deeply entertaining.
It was only night one, but I could already see that my fears had been in vain. For though we weren’t snuggled around a fireplace in flannel pajamas, we were gathered around the dinner table for a grounded, insightful, and admittedly hilarious family chat.
Perhaps we could create Christmas magic in the tropics after all.
After a few days filled with snorkeling, starfish hunting, and sunset strolls with my beloved, we decided to attempt our first big familial test of the trip: lunch at a real, live restaurant with a two-year-old in tow.
My husband, Joe, and I set off with Rose to explore Camana Bay, do a little shopping, and eek, grab a quick bite to eat. Spoiler alert, the only store we popped into was a toy store before our water baby spotted the massive water fountain extravaganza.
She stripped down to her diaper, as if she owned the place, and immediately set about the work of being a kid on holiday. I don’t even have the words to capture the amount of joy and giggles that emanated from that sweet and exuberant child.
No clothes. No towel. No problem.
Appropriately dressed again, it was time for lunch. Determined to set ourselves up for success, we decided on Loco Cayman because not only was it Taco Tuesday (duh!), but Rose will always devour a shrimp quesadilla. Sometimes you have to go with what you know.
I’m not exaggerating when I say that this was hands down the very best lunch we have ever had as a family of three.
Rose colored happily for what felt like days, scarfing down her entire adult-sized entree, and then sampling chips and guacamole long enough for Joe and me to enjoy our own meals; the whole thing. Not a bite, not a shovel of food to the face. But several overflowing taco masterpieces, dripping with pico de gallo and Mexican slaw.
From sweet Caribbean lobster to zesty marinated grilled shrimp with a hint of spice, perfectly crunchy beer-battered snapper, and a few meatier options of carnitas, brisket, and carne asada for variety, we crushed them all.
Aware of the milestone moment, I turned to Joe and excitedly asked, “Have we just turned a corner? Did we just all become best friends?” He smiled happily my way in acknowledgment of how rare that feeling is during this season of parenthood, and took one long sip of his margarita, raising his eyebrows as if to say, “Will you look at that?”
Walking back to the car, another wave of release washed over me. I savored the memory of actually enjoying a meal together. But what’s more, I marveled at the slow but determined evolution of our little family.
The days floated by like sun-bleached driftwood in the shallow waters of the sea. Mornings on the beach. Nap times by the pool, enjoying a Corona Zero and pondering baby names for our second little girl. Afternoons of karaoke in the hottub (mostly singing Prince’s Little Red Corvette), and general goofy sisterness.
It was all a blissful dream, awash with the winter vacation spirit.
And still, I wondered how Christmas Day would land. Would it still feel like Christmas?
We still woke up excited and came straight downstairs in our pajamas. We ripped open presents under the tree. Ok, so it was a felt tree for Rose, and she was the only one who opened presents, but her happiness was shared by us all. We danced and laughed per usual.
It was everything I needed on a Christmas morning and then some.
The final test was Christmas Lunch. Could it bring the well-worn emotional architecture of the holidays, even in such unfamiliar settings?
The short answer is yes, it could.
We decided to bring a chef into the villa we called “home” for the week so that we could all stay as relaxed and effortless as possible. We wanted that lazy, roll-up-to-the-table-after-snacking-all-day kind of vibe, and Chef Remy delivered. With interesting dietary restrictions amongst the group, the easiest cuisine to suit all palettes was actually a Greek feast. And feast we did!
After a quick post-beach shower, Rose snuggled sleepily in my lap, wearing nothing but her diaper, and chatted excitedly with her new bestie, “Chef.” She inhaled more cucumbers, kalamata olives, and hummus than I’ve seen that kid eat in a long time, then went back for more as she gobbled up watermelon and feta skewers topped with chiffonade sliced basil.
As is holiday tradition, I over-ate as well, gorging myself on sunflower-yellow saffron rice and perfectly herbaceous grilled lamb smothered in chilled tzatziki sauce.
The kicker was dessert.
For ten glorious minutes, Rose played with her Santa surprises and colored with my sisters, giving me a moment to exhale into my exhaustion and enjoy my tangy mango mousse without a passenger on my lap. My family gave me a moment of nourishment, and it felt incredible to be so effortlessly held by that table, rather than trying to hold it all together myself.
I’ve said it before, and I’ll say it again: travel with family isn't restful by default. But shared food can create pockets of care, rest, and cozy ease that make it all worth the schlep.
Our final night was supposed to be another adults-only meal on the other side of the island, but after the pace of the holiday, we all felt better staying in altogether for one last supper.
Thankfully, that day, Joe and my sister's partner braved the disastrously windy conditions to go spearfishing and lobstering. They hunted while we hung at home, so we were all thrilled when our dinner suddenly turned into a seafood supper of grouper and some truly enormous fresh-caught lobster.
They grilled it all simply, with just a hint of salt and butter, while we pulled out leftover potatoes, rice, and steamed veggies from the day before. And let me tell you, it was divine. Not just because it was still wet from the sea, but because of the shared effort they expended to catch it.
They were proud and exhausted. We were present and well-fed. I guess that’s what happens when effort, family, and sustenance collide.
As the trip wound down, I was admittedly surprised by the outcome. It wasn’t what I expected, and it wasn’t without its family scuffles, but it was punctuated by some truly meaningful moments.
It was the people at the table who brought the vibes I needed. The shared meals that slowed us down long enough to actually hear each other. Those are the holiday memories I’ll take with me. Those are the traditions I want to carry on, no matter where the winter holidays bring us next.
Ultimately, I’ll remember what was said even more than what was served.
Well, except for the lobster on the last night, that thing was huge!
Katherine Rose Woller is a FoodFamilyTravel.com contributor. Her travel advice has been seen in Forbes, her parenting insights in Parents and The Bump, and her words in The Mother Chapter.
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