When your best friend emails you that she wants to go on a girls trip with some of our amazing friends, you immediately say yes. What made the trip even better is the fact that we would be celebrating her bachelorette. Not only were 5 of us headed to the picturesque and beautiful Cayman Islands, but we had a reason to celebrate while we were there. Thus, this trip quickly became one I am never going to forget.
I’ve known my BFF Natalie for almost 7 years. We met in New York City in 2012 when I was Miss USA and she was working as the social media manager for a luxury brand. We immediately hit it off, and every time I am in NYC, Tor and I always stay and spend time with her. I was so touched to be invited along on this trip, especially since I do not get to see her as often as I used to with me being based in Los Angeles. Even though I am terrified of flying solo or without Tor, I was determined to put my fears aside to be there for my bestie. So I hopped on a plane in Los Angeles and traveled east for the adventure that was to be called “Natchelorette“.
Prior to this visit to the Cayman Islands, I had not spent much time in the Caribbean besides the Bahamas. I was excited to head somewhere tropical and with four amazing friends in tow. We all met up in Miami and then hopped on a plane together to Grand Cayman, the largest of the Cayman Islands. I could see paradise from my plane window before we even touched ground. I had been told that the Cayman Islands are surrounded by the bluest waters you’ll ever see. That statement hardly does them justice. The color of the water is this undeniable cerulean, with pops of white as the waves crash about. The sand is so pure that it almost looks completely untouched. The breeze in the air is warm with a salty scent of ocean water and flowers. The sounds all around you are that of palm trees dancing in that same breeze. And those sunsets were a perfect marriage of oranges, reds, and violet, with all colors being mirrored on the water.
We stayed at the Kimpton Seafire Resort, which immediately felt like home to us. We were put up in two bedroom bungalows, both of them just steps from the beach and overlooking the water. Our bungalows faced west, so we were lucky to have those magical sunsets be our evening entertainment. Located along Seven Mile Beach, it could not have been in a more perfect, central location for all of our activities for the next 4 days.
For our first full day in Cayman Islands, we were scheduled to sail with Cayman Luxury Charters on a private yacht to go snorkeling, swim with string rays, and do some jet skiing (which I have still yet to do!). Unfortunately, I am easily prone to seasickness, and since the winds had been picking up all week (unbeknownst to all of us, it was the start of Hurricane Michael out to sea), the waters were bound to be a bit choppy. I sat out from the boating day, but waved my friends off from the pier before returning to the hotel. I ended up spending a much needed day of doing absolutely nothing. I immersed myself in the hotel’s large and very warm pool, and I continued to read a book about the history of The Wars of the Roses as well as ordered a lobster roll and rosé to enjoy poolside. I hadn’t enjoyed a day of doing nothing in a long time, and it was hard to not want to keep looking at my phone. But a disconnect while in the Cayman Islands was necessary.
For our first night, Kimpton Seafire Resort pampered us with a multi-course dinner on the lawn of our bungalow overlooking the ocean and the sunset. After the sun set and the moon and stars came out to play, whilst surrounded by tiki torches, flowers, incredible island cuisine, and several bottles of wine and champagne, we spent hours laughing and talking like girlfriends do.
The next day, we woke up early to enjoy some paddle board yoga on the ocean water just steps from our bungalow. Due to my seasickness, I had to withdraw about 10 minutes into the hour long session, but that doesn’t mean I didn’t get to enjoy swimming in the most refreshing ocean water I have ever felt. The best part of the morning was the unexpected rain. As we began our initial paddle out to sea, the skies went from ocean blue to charcoal grey in under a minute. Then suddenly the clouds opened up and unleashed the most refreshing downpour. There was something so magical and beautiful about that downpour. It felt like that unforgettable scene in The Notebook when the rain began to fall and you choose to live in the moment instead of running for cover.
That afternoon, we departed for lunch in town at The Brasserie where most of us devoured some of the best burgers we’ve ever had. Afterwards, we were driven about 40 minutes east to the other end of the island to explore Cayman Crystal Caves. There are hundreds of underground caves located deep within Grand Cayman’s forests, twinkling like stars when the proper light is applied inside it. It’s almost as if these caves were the KiraKira app come to life.
Dinner that night was over the water at The Lobster Pot, on a second story deck looking out to the dark, endless sea with the stars shining brightly overhead. While ordering nonstop rounds of coconut shrimp and red wine, we could hear the waves crashing below us. The yachts in the distance tossed about in those waves, and the cruise ships departing for Cozumel could be seen all lit up in the distance as they became faint marks on the horizon.
The next morning, the first rains of what would eventually become Hurricane Michael had made their entrance overnight. In fact, it was a lovely sound to hear in the middle of the night as the rain hit all the windows in my room. There’s something peaceful about rainfall when in the tropics, even at night. With our kayaking adventure cancelled for the morning, we took our time enjoying breakfast on the hotel restaurant’s covered patio, splitting banana waffles and breakfast quesadillas. Our afternoon was to be spent in the best way after such a wonderful week in paradise – at the spa. After a good steam, an hour long massage, and a dip in the jacuzzi with an open ceiling to the tropics above, I could not have felt any more relaxed.
We ended our amazing time in the Cayman Islands at the Italian hotspot Ristorante Pappagallo for dinner. As we ordered rounds of pasta, burrata, and red wine whilst surrounded by parrots, we couldn’t help but reflect on the wonderful experience we had together in the Caribbean.
After months of planning the perfect trip, we were sad to recognize it was all coming to an end in just a few hours. The Cayman Islands had been absolutely incredible to us, and it was a girls trip none of us are ever going to forget. As we toasted our girl in celebration of her upcoming nuptials, we also toasted to new friendships that had blossomed underneath the tropical sun over the last 4 days.
Looking to plan your Cayman Islands adventure? Be sure to check out my Cayman Islands travel guide here.