Travel has always been a profound passion, offering a gateway to uncharted territories of experience and unexpected life moments. Some of these encounters are utterly exhilarating, while others verge on the truly astonishing, stretching the boundaries of what one considers possible. This past week, I embarked on a journey to my 52nd country, Jamaica, to immerse myself in a photography and blogger retreat – an adventure that unveiled a plethora of experiences I never knew I needed until I set foot on this vibrant island.

TL;DR: Short on time? Here are my top unexpected finds and travel essentials for Jamaica:
🏨Hotels and Vacation Rentals for Your Jamaican Escape
📍Discover Unforgettable Tours and Activities in Jamaica
Unforgettable Jamaica Travel: Experiences I Never Knew I Needed
Unexpected Discoveries: The True Essence of Jamaican Adventures
The retreat provided an incredible opportunity to connect with fellow creatives and entrepreneurs. I reconnected with dear friends Amy from Mom Spark and Amy from Living Locurto – it seems I have a knack for finding amazing friends named Amy! This trip also introduced me to Tracy from Shutterbean, a truly fantastic individual and a fellow Leo, who happens to be an incredibly talented photographer. These connections forged an enriching layer to the travel experience, proving that some of the best parts of any journey are the people you share it with.
Participating in this blog and photography retreat in Jamaica was more than just honing my skills; it was about being in a room filled with other female business owners who genuinely understand the unique challenges and triumphs of this lifestyle. There’s an unparalleled camaraderie in sharing experiences with those who navigate the same complex balance of professional ambitions and personal life, all while chasing their passions across the globe.
Yet, amidst the networking and skill-building, Jamaica unfolded itself in ways I could never have anticipated. The island revealed a series of moments that were both bewildering and beautiful, creating memories that are now etched into my travel diary as essential life experiences. So, let’s delve into the specific things I didn’t know I needed in my life until I arrived in the captivating embrace of Jamaica.



Witnessing a Synchronized Swimming Show, Phantom of the Opera Style
Picture this: you’ve just finished a delightful dinner at the Hyatt Zilara, stepping out into the balmy Jamaican night, only to stumble upon an enthralling fire and water show. This wasn’t just any poolside entertainment; it was an elaborate synchronized swimming spectacle themed around “The Phantom of the Opera.” Costumed performers glided and twirled through the water, executing movements that were both graceful and astonishing. For much of the show, I found myself wide-eyed, questioning if what I was witnessing was truly real. No, it wasn’t the cocktails; it was simply an unexpected and breathtaking display that defied my imagination. The sheer artistry and precision were so spectacular, it felt almost dreamlike. It was a truly unique blend of theatrical performance and aquatic skill, a memory I dearly wish I had captured on video, though my phone battery, unfortunately, had other plans.

Experiencing a Fiery Rum Shot
While the shot itself wasn’t directly on fire, the presentation was certainly dramatic! Our charming waiter ignited one of the shot glasses, and the flame danced mesmerizingly as we prepared for our turn. He declared with a smile that no “pretty lady” could leave Jamaica without trying a rum shot. The exact blend remains a mystery, but the experience was anything but mundane. The moment the potent liquid went down, a fiery warmth spread, leaving an unforgettable, burning sensation. It was a bold initiation into Jamaican spirits, a moment of shared laughter and surprise that perfectly encapsulated the adventurous spirit of the trip.

Savoring a Bob Marley Cocktail
Some experiences, you simply know you need. The iconic Bob Marley cocktail was one such item on my mental checklist, though I wasn’t entirely sure if the opportunity would arise. Having seen these vibrant, layered drinks splashed across social media countless times, I had long yearned to try one. My first drink order by the pool in Jamaica was, naturally, the Bob Marley, and it absolutely lived up to the hype. With its striking red, yellow, and green layers, representing the Rastafarian flag, each sip was a burst of tropical flavors – a truly delicious and refreshing treat that felt quintessentially Jamaican. It was a “hello yum!” moment that instantly transported me deeper into the island’s relaxed vibe.

Dining in Almost Complete Darkness: An Unexpected Culinary Adventure
One evening at the Hyatt Zilara, we found ourselves at Urban Heatz, their international cuisine restaurant, for a truly unique dinner. Upon being seated, we received an odd instruction: “Don’t move your silverware.” Of course, as seasoned bloggers, our first instinct was to rearrange everything to accommodate our phones for optimal photo opportunities! After a quick correction and repositioning of our cutlery, we were told to wait. Suddenly, with a dramatic flourish, our waiters swept our silverware aside and gracefully placed napkins on our laps. This theatrical start hinted at the quirky evening ahead.
The restaurant was so dimly lit that mini flashlights were provided just to read the menus. Throughout the meal, we relied on our cell phones to illuminate our plates, trying to discern what delicious morsels we were actually eating. It was a hilariously random dinner experience, full of speculation and surprise. This shared adventure of fumbling in the dark created an instant bond among my tablemates as we collectively wondered what delightful, or perhaps peculiar, event would unfold next. It transformed a simple meal into an unforgettable, sensory journey.

Indulging in a Cabana with Personalized Butler Service
This was a dream I hadn’t dared to articulate – a day spent in a luxurious overwater cabana, complete with personal butler service. Who wouldn’t fantasize about such an experience? For one magical day, this dream became a reality. Lounging in comfort, overlooking the sparkling turquoise waters, with every whim catered to, felt utterly sublime. At one point, amidst the enjoyment of several Bob Marley cocktails, I realized I’d forgotten about lunch. Just as the thought crossed my mind, our attentive butler appeared as if by magic, presenting me with a plate of crispy french fries and a refreshing salad. He also ensured a steady supply of ice-cold water, perfectly balancing the vibrant cocktails. It was an unparalleled level of pampering, making the day feel truly special and deeply relaxing, an absolute highlight of my Jamaican escape.


Embracing Body Confidence: Taking Pictures in My Swimsuit
Let’s be honest: for most of us, posing in a swimsuit isn’t exactly a natural or comfortable occurrence. My usual preference is to be behind the camera, capturing the world around me. However, my time in Jamaica seemed destined to challenge this habit. While happily snapping photos of others jumping into the pool, I was playfully called out – “Your turn!” My initial reaction was an emphatic “No! Seriously, no!” Yet, propelled by the encouraging spirit of the group, I actually did it. I posed in my swimsuit, attempting to leap and catch air as I plunged into the refreshing pool. This wasn’t on my itinerary, but I’m incredibly glad it happened. It was a significant step outside my comfort zone, breaking through a personal fear, and now I’m even posting the pictures – holy heck, indeed! This empowering moment taught me the value of embracing vulnerability and celebrating self-acceptance, a powerful lesson unexpectedly learned in Jamaica.
Exploring the color blue in Jamaica today. Spent the morning on a photo walk working on photo styling, manual settings, and pushing our comfort levels in photography. It was eye opening to see other photographers work and see what they focused on versus what I photographed. So excited to be in Jamaica this week really focusing on photography and upping my skills and understanding of my camera.
A photo posted by Tammilee Tillison (@tammileetips) on
The Photographic Challenge: Focusing on the Color Blue
During our photography retreat, we engaged in a fascinating exercise: breaking into groups for photo walks, each tasked with focusing on a specific color. Our team was assigned “blue” – a surprisingly easy yet creatively stimulating challenge in a place like Jamaica! The abundance of azure skies, turquoise waters, and vibrant blue accents across the landscape meant that opportunities were everywhere. This focused approach compelled me to look for unexpected pops of blue throughout my entire stay, forcing a shift in perspective. It served as a powerful reminder to seek out the unusual, to capture details I might otherwise overlook, and to find beauty in subjects beyond my typical photographic repertoire. For any aspiring or seasoned photographer, I wholeheartedly recommend this challenge: pick a random color and let it guide your lens. You’ll be amazed by the new types of photos you capture and the fresh insights you gain.

Attending Another Michael Jackson Impersonator Show
It seems I’ve developed a curious streak of encountering Michael Jackson impersonator shows on my travels. Having recently enjoyed one in Puerto Vallarta, I was delightfully surprised to find another vibrant performance during my time in Jamaica. This particular show, held against the backdrop of the lively resort, was truly “WOW!” The energy, the iconic dance moves, and the sheer dedication of the performer captivated the audience, creating a nostalgic and exhilarating atmosphere. It’s these unexpected, joyous performances that add an extra layer of magic to international travel, reminding you that entertainment, much like culture, has many fascinating facets.

Watching ‘Cool Runnings’ While in Jamaica
Remarkably, despite my love for travel and inspiring stories, I had somehow never seen the classic movie “Cool Runnings,” which chronicles the incredible journey of the Jamaican Bobsled Team. As fate would have it, during a few relaxing hours at the Montego Bay airport on my way home, I stumbled upon the perfect opportunity. Enjoying a leisurely breakfast at the Bobsled Cafe, I noticed “Cool Runnings” playing on every TV screen. It was an incredibly fitting and heartwarming experience to finally watch parts of the film while physically present in the country that inspired it. While I saw enough to grasp the core story, I now feel an absolute need to watch the entire movie from start to finish, even though I’m fairly certain I already know its triumphant ending. This unexpected airport discovery truly enriched my understanding and appreciation of Jamaican perseverance and spirit.

Sipping a Refreshing Ting
If you’re wondering what a “Ting” is, rest assured, I haven’t lost my mind! A Ting is a delightfully refreshing grapefruit soda, proudly hailing from Jamaica. I’d seen these distinctive green cans at the Red Frog Pubs onboard Carnival Cruise ships, but had never actually tried one until my Jamaican adventure. As someone who isn’t a big soda drinker, the first thing that struck me was the intense carbonation. However, beyond that initial fizz, the Ting revealed a wonderfully crisp, sweet, and zesty citrus flavor that was both unique and incredibly thirst-quenching. It’s the perfect accompaniment to a sunny day in the Caribbean, and a local taste I’m genuinely glad I discovered.


Listening to Bob Marley as the Sun Rises
While relaxing in our cabana, enjoying the tranquil morning, it felt absolutely mandatory to put on some Bob Marley. It was a quintessential Jamaican moment, a soundtrack to the serene beauty of the rising sun over the Caribbean Sea. Interestingly, I was a bit surprised by how little traditional Reggae music, or even Bob Marley himself, I encountered consistently throughout the resort. While they were big fans of popular dance tunes like the Cupid Shuffle and the Wobble (LOL!), this particular moment, intentionally curated by us, truly felt authentic and deeply connected to the spirit of the island. It was a simple pleasure, yet profoundly impactful, completing the idyllic picture of a Jamaican morning.

My brief but exhilarating time in Jamaica was packed with so much fun and an array of unexpected adventures. Even with all these delightful surprises, I’m already dreaming of my next visit. There are still a few essential Jamaican experiences I hope to immerse myself in next time:
- Encounter a true Jamaican Rasta Man: It’s curious that the only Rasta Man I spotted during my entire trip was at Seattle Airport! I yearn for an authentic interaction within Jamaica itself, understanding more about this significant cultural movement.
- Listen to the captivating rhythms of Steel Drums: The vibrant sounds of steel drums are synonymous with the Caribbean, and I’d love to experience their live, resonant melodies.
- Explore more of the island’s diverse landscapes: While the resort offered comfort and beauty, I’m eager to venture beyond and discover the hidden gems, local communities, and untamed natural beauty that lie off the beaten path.
- Discover a pristine white sand beach: Spending a day simply relaxing and exploring a secluded, unspoiled white sand beach is high on my list for ultimate island bliss.
- Hear live Reggae music: Beyond Bob Marley, I want to feel the pulse of live, authentic Reggae music emanating from a local venue, soaking in the soul of Jamaica’s musical heritage.
So there you have it – the crazy, the hilarious, the utterly unexpected, and above all, the truly amazing things I never anticipated experiencing until I journeyed to Jamaica. It was a trip that redefined my expectations of travel, proving that some of the most cherished memories are those you never planned to make.
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