Cuba’s Calling: Creating a Traveler

The terminal at Pearson looked different that February morning in 2014. Not the building itself, it was the same chaotic lineup at security, same overpriced coffee, same departure boards clicking through destinations. What changed was me. I was actually boarding a plane for something other than work, heading somewhere that required sunscreen instead of a laptop, and doing it voluntarily. That alone felt revolutionary for a guy who’d spent decades treating vacation time like monopoly money ie; technically yours, but somehow never actually spent.

From my earliest working days, I was the guy who showed up. Long weekends meant camping trips or throwing a party, nothing that required more planning than loading a cooler and firing up the grill. The concept of “traveling” wasn’t even on my radar. Hell, I didn’t board my first airplane until 2005, and that was for business. The idea of choosing to leave solid ground and fly somewhere warm while Canada was buried in snow? That was other people’s hobby.

Then I met Tina.

When Travel Experience Meets Travel Resistance

My better half couldn’t wrap her head around how anyone could go years without leaving the country. She’d been traveling since forever, racking up passport stamps like I collected fishing lures. When she found out I’d never taken a proper vacation, the look on her face suggested I’d admitted to never trying pizza or something equally incomprehensible.

“We’re fixing this,” she announced one evening.

“Fixing what?”

“Your complete lack of adventure.”

The woman was determined. She also understood that I needed convincing, not pressuring. So when she suggested Cuba in February, when Ontario would be buried under its tenth consecutive snowfall, the timing was suspiciously strategic. Smart move. The thought of warm sand and Caribbean sun while my buddies scraped ice off windshields held definite appeal.

There was another angle too, though neither of us talked about it much at the time. This would be our first real trip together. A week sharing a hotel room, navigating a foreign country, figuring out whether we could handle each other’s travel quirks without wanting to catch separate flights home. It was, as Tina cheerfully pointed out, an excellent compatibility test.

She booked the Caracol Club Amigo resort in Santa Clara. Three stars. All-inclusive. I had no frame of reference for what any of that meant, but Tina assured me it would be perfect for a first timer. Looking back, I appreciate the wisdom in starting with something forgiving rather than throwing me into backpacking across Southeast Asia or whatever.

First Flight: Finding Paradise

The night before departure, we stayed at a hotel near Pearson. Practical move, avoiding the pre-dawn drive to the airport in February weather. We set alarms, grabbed the shuttle, hit the usual checkpoints. Security lines, gate waiting, all that standard airport choreography that I’d done before but never as a prelude to something fun.

The flight itself remains a blur of nervous energy and anticipation. Then we landed.

Santa Clara airport in Cuba is not large or fancy. You won’t find Starbucks or duty-free shopping. But stepping out onto that tarmac, feeling tropical heat slam into you after a Canadian winter? That’s when it started to feel real.

The bus to the resort had cold beer available for a dollar. Best dollar I’ve spent. That Cristal tasted especially good considering the heat and humidity wrapping around us like a warm blanket soaked in seawater. I planted myself against the bus window and just stared.

Palm trees. Actual palm trees, not the decorative ones in mall atriums. Real jungle vegetation pressing against dirt roads. Modest homes with painted walls and tin roofs. Men driving donkeys loaded with produce. Rows of crops with low mountains surrounding them. Motorcycles everywhere. Street dogs everywhere. The whole scene felt surreal, like something from high school geography class suddenly made three-dimensional and real.

My brain started firing on cylinders I’d forgotten existed. Those geography lessons about Caribbean climate zones. History stuff about the Spanish colonial period and the revolution. Political science discussions about embargoes and isolation. All this information I’d absorbed years ago came rushing back, but now it mattered because I was actually there, seeing it, smelling it, experiencing it firsthand. I wanted to know everything suddenly. The whole story.

Tina caught me staring out that window with what must have been a ridiculous expression. She just smiled. She knew.

Caribbean Awakening: Adjusting Attitudes

The resort appeared after what felt like forever but probably wasn’t. Time gets weird when you’re processing an entirely new sensory experience. We pulled up to the Caracol Club Amigo and I dragged my luggage into the lobby for check-in.

Then I heard it. The ocean.

That sound of waves rolling onto shore, steady and rhythmic, ancient and timeless. The smell of salt air mixing with tropical vegetation. A breeze coming in from the Caribbean pushing away the stifling humidity. I just stood there like an idiot, probably grinning ear to ear, taking it all in.

Check-in wasn’t quick with a busload of tourists, but eventually we got escorted to our ground-floor, garden-view room. This is where I learned what three stars means in Cuba. Large, bright room facing the garden. Spacious bathroom. Gated deck with chairs. It had charm, definitely, but up close you noticed the age – worn furnishings, dated fixtures, faded fabrics, water stains on the ceiling. None of that mattered. This was just somewhere to sleep.

The beach had exactly what you’d expect from Caribbean advertising, plenty of chairs and umbrellas, white sand, turquoise water. The buffet was serving when we arrived, so we dove in. The food was solid, nothing fancy, but the shrimp? Ridiculously good. Fresh seafood is always best when you’re literally steps from where it came from.

After touring the grounds, we settled at one of the bars for evening drinks and watched the sunset paint the sky in colors that seemed Photoshopped but weren’t. Then we crashed early. Travel exhaustion plus sensory overload equals excellent sleep.

Beach Life: Basking Blissfully

Early risers by nature, we hit breakfast and headed straight to the beach armed with sunscreen, books, headphones, sunglasses, and towels. That first full day of lounging on a Caribbean beach in the middle of a Canadian winter changed something fundamental in my thinking about life.

I’d spent decades working through vacation time, banking those days like savings that never got spent. Sitting there in the sun, toes buried in warm sand, watching waves roll in, hearing people laugh and splash in the surf, it all made me question what the hell I’d been doing with my life. This feeling of complete relaxation mixed with energizing contentment seemed impossible yet there it was. Real. Present. Available to me if I’d just been willing to take it.

Looking around at palm trees swaying in the breeze, feeling the sun warm my skin, wandering back and forth to the beach bar for fresh beverages, jumping up and down in the waves like a kid, these experiences stuck with me. Years later, I still carry them. I’m glad about that. Everyone who makes their regular sojourns south (or anywhere) should bring back and maintain that sense of appreciation, of gratitude for that sense of great worth from their travels.

We spent that entire first day just drinking in the location. And drinking actual drinks. The local Havana Club rum mixed with fresh fruit juice tastes completely different under a palm tree than anything back home. Lunch, more beach, eventually back to the room to shower for dinner. Another buffet, decent food if lacking some savouriness, but I wasn’t complaining. My cheeks hurt from smiling when I finally fell asleep that night.

Vendor Adventures: Venturing Voluntarily

Day two brought more of the same blessed routine. It also introduced us to the beach vendors. Cuba has many. More than we’ve encountered elsewhere, but they all responded politely to “no gracias.”

One particular vendor caught our attention. While browsing his wares, he asked if we liked seafood. We love seafood. That opened the sales pitch for a romantic evening adventure: a fresh lobster dinner delivered as part of an authentic Cuban experience. A horse-drawn carriage would collect us from the resort and take us to a private beach for drinks and swimming. Then we’d head to his friend’s house for the lobster dinner. Finally, we’d return to the hotel in a classic 1950s car.

Every alarm bell in my head went off. Safety risk. Security nightmare. Sketchy as hell. Tourist trap written all over it.

Tina staunchly defended the idea. Cuba is one of the safest countries in the world, especially for tourists, she insisted. We should absolutely take him up on it. We argued. She won. We went.

Best decision of the trip.

Everything happened exactly as promised. The horse-drawn carriage ride felt romantic and nostalgic. The private beach offered quiet swimming and cold drinks. But the real magic happened at the local home where they served us a full-course lobster meal that I can still taste years later. Being welcomed into someone’s actual house, seeing how they lived, sharing a meal prepared in their kitchen, that moment made the entire trip worth it. That’s when I started falling in love with travel and Cuba particularly.

We got dropped safely back at the resort entrance. I happily handed over twenty US dollars for an evening that would’ve cost five times that through official channels and been far less memorable.

Returning Reflections: Realizing Revelations

The rest of the week followed a pattern – beach, food, drinks, conversations, repeat – and I never tired of it. The simplicity felt luxurious. The routine felt freeing. Each day reinforced that Tina and I worked well together as travel companions. We talked, we laughed, we shared knowledge about Cuba from our different perspectives. She brought the experienced traveler’s practical insights. I brought the geographical, historical, and political context I’d been researching and remembering. We complemented each other.

Neither of us knew at the time that we’d return to Cuba just a couple years later to get married on a beach. That week in 2014 simply proved we could handle traveling together, which turns out to be more important than people realize before they commit to someone.

Cuba is an amazing country with rich history and vibrant culture. It’s had more than its share of troubles, both politically and environmentally. The ongoing US embargo shows its effects everywhere you look, and hurricanes routinely batter the island nation, but still the people persevere with smiles and resilience. Of all the places Tina could have chosen for my first off-continent experience, I’m grateful it was Cuba.

That trip was the jumping off point for me. It’s where The Beery Traveler was truly born. It gave me the inspiration to chronicle our travels, to share experiences, to encourage others to take that first step into a bigger world. I’m not the best writer, and I can’t always find the right words, but that trip to Cuba gave me something to write about. It’s responsible for my continuing efforts to tell these stories.

Maybe one of you will read this and decide to take your own first trip. Maybe you’ll start documenting your travels. Or maybe you’ll just enjoy reading about mine. Either way, that February week in Santa Clara, Cuba changed my life. Sometimes the best things happen when you stop resisting and just say yes to the adventure.

If you’re ready to take your own first step into international travel, or if you need help planning that perfect Caribbean getaway, Boarding Pass Travel specializes in making first-time international trips stress-free and memorable. We particularly love helping people discover Cuba and other Caribbean destinations that might just change your life the way Santa Clara changed mine.

For those considering their own Cuban adventure, I’d strongly recommend taking a chance on those authentic local experiences like our lobster dinner excursion. Just make sure you’re working with reputable people and listening to your instincts. And if you’re nervous about that first international trip, consider reading about how travel can transform your perspective or why slowing down your travel pace often creates the most meaningful experiences. Sometimes the best journeys happen when you let go of rigid plans and embrace the unknown.