On a particularly frigid NYC morning, I was more than ready to trade in snowflakes, 27 degrees, and hot cocoa for palm trees, 85 degrees, and piña coladas. As much as I enjoy the chocolatey beverage, I was about to embark on my first tropical Christmas vacation with my bestie — to Grand Cayman, no less — where we definitely wouldn't need any hot drinks to keep us warm.
Grand Cayman is listed as one of American Express Travel’s top 2020 travel destinations, based on where the company's Platinum Card Members have already booked getaways through the next year. So, over the course of three days in early December, I got a sneak peek at the Caribbean hotspot, along with one of its coolest resorts, to find out why the island is so trendy and popular among 2020 travelers.
As I explored this paradise — which included tinsel and seashell-adorned Christmas trees along the beach — it was clear to see the holiday spirit on the island was as incredible (and as strong) as the rum; palm trees were dressed in twinkly lights, and restaurants and boats were decked out in wreaths and beachy holiday decor. It was as if Santa himself sprinkled his magic across this tropical haven. Even the shuttle had Christmas jams streaming while I made my way to the Kimpton Seafire Resort + Spa, a Fine Hotels & Resorts property, which hosted my ultimate holiday escape.
Curating a well-rounded vacay from start to finish can be a struggle when you’re traveling to a new place, and scouring the web for recommendations of cool hidden gems can be a tedious task when all you want to do is shop for new bikinis. Plus, around the holidays, you already have your hands full with gift shopping, cookie swaps, and holiday parties. Fortunately, I had my whole itinerary at the Kimpton Seafire mapped out for me by an American Express Travel & Lifestyle Consultant in advance, and it was honestly a millennial’s dream come true. (Guests at the Kimpton who are Amex Platinum Card Members can take advantage of this benefit of having their entire itinerary exclusively planned out by a consultant like I did — at no additional cost — for the most seamless, stress-free process.)
The next two days were so Instagrammable and enjoyable; my itinerary included the perfect mix of activities that put me in a super relaxed yet festive mood. I mean, I got to sip holiday cocktails in a life-size gingerbread house made out of real gingerbread. If that doesn't scream Christmas, I don't know what does.
The resort’s gingerbread cocktail bar was made with pounds upon pounds of spiced cookie dough, candy, and icing. My Christmas-obsessed self fell in love with this particular spot upon arrival. Enjoying the Rum and Crumble cocktail (cookie-infused coconut rum, cream, and white cacao) and Winter Sangria by the bar’s faux fireplace was a sweet treat that made me feel like I was at home in New York, even though I was far from the chilly East Coast.
To put the cherry on top of my day of relaxation, I soaked in an Insta-worthy, freestanding bathtub in my ocean-view suite, popped a bottle of champagne, and enjoyed chocolate-covered strawberries on my balcony in a plush bathrobe and slippers.
When I ventured outside the resort, I boated to Stingray City — sandbars where you can chill and snorkel with a bunch of stingrays — and enjoyed fresh ceviche the first mate — the captain's right-hand guy — caught straight from the sea that very afternoon and prepped on the boat. On top of it all, I experienced some of the perks of being an American Express Platinum Card Member: breakfast for two on the daily, guaranteed late checkout, noon check-in, and more unique amenities (like spa or food and beverage credits).
The next day in Grand Cayman, I cruised over to Kaibo, the most Christmasy beach bar, with Big Lex Charters, which any traveler on the island can sign up for. This boating excursion was my version of complete and utter paradise, with a little festive touch. Our table just so happened to be planted next to yet another Christmas tree in the white sand, which I reveled in while I sipped my drink out of a coconut in the warm sunshine.
After indulging in tacos at the beach bar, I held a starfish in my hands at a sandbar — while being surrounded by even more stunning starfish — kissed a stingray — which, according to legend (and the boat’s first mate), apparently brings seven years of good luck — and even got a stingray “back massage” for a couple of minutes. The captain of the boat held up the stingray’s soft tummy to my back and I immediately squealed with surprise and delight. It felt so cool, a tad slimy — likely not for the squeamish type — but all around a true bucket list gem.
I spent the next afternoon taking a break from all of the amazing excursions and got a relaxing massage (sans stingrays) back at the resort’s spa, compliments of the hotel. The rest of the day was mostly spent enjoying mimosas and snacks in a cabana next to the infinity pool, which is conveniently located steps away from the most 'Gram-worthy spot, Seven Mile Beach.
Later that night, I visited a local beach bar called Calico Jack's, which is a short walk down the beach from the Kimpton, where there were Christmas lights strung up on the deck over the sand and people jamming out in Santa hats. Of course I wanted to get in on the festivities, so I ordered a beer at the bar with my bestie and we danced the night away under the colorful lights.
Sunshine, starfish, a stingray massage, and Christmas trees in the sand are the treats I never knew I needed this time of year. It was like Christmas came early. Overall, I can definitely see why the island is one of 2020's top travel destinations. If you're looking to treat yourself to the best tropical getaway of all time, I highly recommend heading over to the Kimpton Seafire's website ASAP, or if you're an Amex Platinum Card Member, booking via Amex to soak up the extra perks.