The Ultimate Cayman Island Adventure

Kimpton Seafire Resort + Spa Stingrays, horseback riding and Havana Nights came together to form the ultimate Cayman Island adventure.

If you’ve read my Travel Log article on The Amalfi Coast, you know all about my good fortune in meeting G, who lets me tag along on his yearly, all expense paid work trips. Our excursion to the Cayman Islands is the second trip I have had the privilege of attending and was truly the adventure of a lifetime.

Day 1 | Flying out of JFK & Arriving in Paradise

I am a morning person. I work from 6A-2P and am used to waking up regularly at 4:30 to start my day. I’m not saying that it is fun, of course I’d rather stay in bed all morning, but I’m used to it. G is not a morning person. He works late into the night and unless he absolutely has to wake up, he prefers sleeping in. When he told me our flight would leave from JFK at 7:30a, I couldn’t help but laugh. How is he going to get up, pick me up and get us to the airport in time? I decided to trust that he could make it work, and, like always he did. We got there with time (and by that I mean minutes) to spare, got on the plane, and settled in for our 4 hour flight to the Cayman Islands.

Upon arriving at Owen Roberts International Airport, we waded through customs and were settled comfortably in a van reserved just for employees of G’s company. We wound our way past the crystal clear ocean and through a tropical paradise while chatting with our fellow passengers about the excursions we chose and the parties still to come.

Kimpton Seafire Resort + Spa RoomOur hotel was situated on 7 Mile Beach, arguably one of the most beautiful beaches in the world. When we arrive at the Kimpton Seafire Resort + Spa, we entered the vaulted ceiling, airy lobby and were greeted with champagne, gifts and an itinerary for the days to come. Our room was equipped with two double beds and was decorated in hues of red, orange, dark gray and white. At the far end was a balcony with comfortable furniture, perfect for lounging, and an amazing view of the ocean and resort grounds. Just steps from the beach, The Kimpton Seafire Resort + Spa is an intimate resort featuring a beautiful, secluded pool, multiple restaurants, walking paths and a gym.

We were starving after a long flight so we headed downstairs to the beach front restaurant, Cocoloba Bar and Grill. The fish tacos are highly recommended. The ambiance was sublime with sweeping ocean views and open air environment. Feeling satiated and refreshed, we headed to the pool where there were other company employees cooling off and chatting about work and their trip. It was so nice to have a drink and relax after a long day.Fire Thrower Kimpton Seafire Resort + Spa

That evening, the company threw a welcome party on the beach. Bare feet were encouraged and sandals and flip flops piled up outside the arched entryway to the plot of beach designated for our celebration. We were greeted with a drink, a quick photo and a sunset view of the amazing shoreline. The food was tasty and plentiful. There was a massive sand sculpture of the company logo. Later in the evening, fire throwers, choreographed to music, put on a thrilling show. At the end of the evening, we slowly made our way back to our room, full, exhausted and feeling great!

Day 2 | Stingray Excursion

Swimming with Stingrays, Cayman IslandsG had a meeting the next morning so I went to get breakfast on my own. The buffet offered everything from eggs and bacon to yogurt and fresh fruit, all impeccably presented and masterfully prepared. I chatted with my fellow plus ones while I enjoyed coffee on a sweeping terrace overlooking the beach and hotel grounds. I could have sat there for hours enjoying the breeze, the salty scent of the ocean, and watching the little birds patiently waiting for the next crumb to drop.

When the meeting was over, we went up to our room to get ready for the sting ray excursion. This is one of the activities that the Cayman Islands is famous for. I’ll admit, I was a bit nervous about swimming with these massive fish with their enormous wings and potentially poisonous tails, but I pushed those thoughts behind me as we got on a bus that would soon take us to the catamarans to Stingray City.

When we arrived for our Stingray City Tour, four pristine catamarans floated lazily in the bay adorned with company flags, waited to take us on our journey. We climbed aboard, drink in hand and sunscreen heavily applied. When we reached the sandbar, there were other catamarans in the water with tourists swimming with the rays. We were given snorkeling gear and quickly hopped in the water. It was warmer than I expected and only about chest deep. G and I followed our guide as he talked about the stingrays, how to handle them, where it was safe to touch, and what to expect. It wasn’t long before we were surrounded by these beautiful and graceful creatures. It was invigorating and overwhelming. They glided between us, fins, slick and smooth, welcoming the attention of our hesitant touch. I watched as some of our companions even went as far as holding them in their arms. We donned snorkels and masks and swam down to the ocean floor, seeing it through the stingrays’ eyes. This silent, magical world was beyond anything I could imagine. At long last, the catamaran crew corralled us back on the boats and we sailed away, delighted and in awe of our experience.

The next stop was a private beach where we were presented with drinks in coconuts and a barbecue lunch. There were blowup slides in the water that some brave guests attempted to try. A few guys started to toss around a football while others were lazing on beach chairs, soaking up the sun. It was a lovely, relaxing end to our first Cayman Islands adventure.

Upon arriving back at the hotel, we immediately crawled into bed for an afternoon nap before getting ready for dinner than night.

Day 3 | Horseback Riding & Havana Nights

Horseback Riding on the Beach, Cayman IslandsIt felt good to roll out of bed and not have to be anywhere the next morning. I couldn’t wait to introduce G to our lovely breakfast spot so as soon as we were up we went down stairs and leisurely drank our coffee and fueled up for the day. G spent most of the morning on our balcony catching up on work while I read my book, relaxing and breathing in the salt air.

G signed us up for horseback riding in the afternoon. I have been on a horse exactly one time in my life, at 11 years old, and I was far from an equestrian. Needless to say, I was pretty nervous about this activity. We hopped on a bus that took us to a different part of the beach that was very narrow and a bit briny. We waited and waited and finally our guides showed up with the horses. I immediately told one I had no idea what I was doing which prompted eye rolls from G and extreme coddling from our leader. He helped me on the horse and we walked around a bit while I started to gain a bit more confidence. He then described what to expect on our journey. First, we would take a ride down the beach to a certain location, then we would take the saddles off of our horses, hop back on, and ride bareback deep into the ocean. All I could think was, you have got to be joking me, but no sooner did the thought cross my mind, then we were off, in a line, following out trusty leader down a narrow strip of beach. After a few minutes of riding, surrounded by lush greenery and the sounds of the waves rising up the shore, I started to relax a little. I chatted with the guide and talked (and even sang a little) to my horse, attempting to keep him focused and moving at an acceptable pace. G was behind me on his horse cracking good-natured jokes at my expense. He’s lucky I can laugh at myself! I really felt like I was getting the hang of this and my horse and because fast friends.

When we arrived at the point where were to take off the saddles, we took a quick break to apply more sunscreen and rehydrate. The guide then removed the saddles and proceeded to tell us that we were going to have to jump onto the horse from the hind quarts. He demonstrated, making it look east as pie and then chose another girl in our group to be the first victim. She tried and tried to no avail, while we all stared in horrified amusement. When we just couldn’t take it anymore, we were told that the whole thing was a joke and that he would help each of us get on our horse. Needless to say, the girl was not laughing. He gave her a boost on his knee and she was up and running. G decided that he was going to hop on with no help, like the show off that he is, and succeeded. Everyone else needed a boost. When at long last it came time for me to get on, our guide lead my horse to a crudely assembled set of wooden stairs so I could easily climb on to my trusty companion. Yes, it was embarrassing, but I don’t dwell on that stuff much anymore. I was just happy to be on the horse!

We lined up and our horses slowly made their way into the water. I relaxed and let my horse do what it needed to do which seemed to work. We were a team. At one point, the horses were actually swimming. If I looked down I could see deep into the crystal clear water. I could hear my companion behind me in a bit of a panic, but I stayed confident and trusted that my horse knew what he was doing. It was an amazing feeling, being on such and massive animal out in the middle of the ocean. I felt free and completely in control. My horse and I were one. We made our way back up the beach, the way we came, exuberant about the adventure we had just taken.

Havana Nights Party

Not long after, we got into the bus and went back to the hotel just in time to get ready for the Havana Nights Party. We were dressed to the nines when we arrive at the party a few hours later. The ladies were given fans and the men received fedoras. We got our pictures taken in front of a cherry red, classic car right out of the streets of Havana. There were cigar rollers, fortune-tellers and live music, perfect for dancing. Oh, the dancing. It is my favorite part. I’m not the best, but I’d like to think that G makes up for that, because he has a natural rhythm. The ambiance was perfect, a world frozen in 1950s Cuban jazz club glory. Not a detail was forgotten from the food to the flowers on the tables, it was like traveling back in time. Nothing could top this decadent soiree.

Day 4 | Recovery

7 Mile Beach, Kimpton Seafire Resort + SpaAfter three days of nonstop excitement, drinking and excursions we needed a break. I spent the day on the beach, reading my book and enjoying the quiet. G went to the pool and socialized with his friends. We had one final dinner to get ready for that evening and then it was back to reality.

The final dinner took place at a restaurant off the resort on the water. It was raining off and on that evening, giving the entire place a shimmer when the sun played peekaboo from behind the clouds. It’s like mother nature didn’t know what she wanted, so she gave us both sunshine and rain simultaneously which resulted in the most beautiful sunset imaginable, rays streaming through drops of condensation making the whole place glow and sparkle.

Cayman Islands SunsetThere was food, drinks and speeches. Excited chatter of next years trip to Hawaii filled the air. We got our pictures taken and arranged in photo booth strips. We released lanterns into the night sky over the ocean while Get Lucky by Daft Punk played in the background. We danced and talked and laughed. It was the perfect end to our Cayman Islands Adventure.

Day 5 | Homeward Bound

Melancholy settled around on the bus back to the airport like a fog. We quietly made our way to security, got on the plane and prepared ourselves for the long journey home. Another amazing trip lingered in my mind with experiences I will never forget.


  1. Thanks for this wonderful recap of your ultimate cayman island adventure! Your excursions sound like they were absolutely incredible. The experiences were once-in-a-lifetime! It’s always nice to check out a new part of the world, and the hardest part is coming home and getting readjusted to normal life. Many happy travels to you!

  2. What an amazing trip! The Cayman Islands have been on my list of places I’d love to visit for years, now. The Stingray happens to be the mascot for my city’s hockey team, so I have a special fondness for them – I’ll definitely have to go snorkeling with them, someday.

    All your pictures are so nicely spaced. I feel like there’s a good number of them, for an article this long. I also like how your voice is very clear, and obviously you. I can tell from your writing, you really know who you are and what you’re about, and that made the article all the nicer to read.

    1. admin

      Thanks so much, Emily! I guess I am unapologetically me in most cases! You would love the Cayman Islands. It’s truly a magical place and well worth the trip. If you have any more questions, please feel free to ask!

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