Xena, Warrior Princess of Trinidad and Tobago

Another exciting flight out of San Luis Obispo on United Express.

How do you know when you’ve bitten off more than you can chew?

The irony is, you usually don’t—at least, not until you’re way too far down the rabbit hole, wondering if you’ll ever find the way out. Life has this way of nudging you along with misplaced confidence, as if to say, “Keep going, you’re doing great!” when really, you’re holding a one-way ticket to chaos.

For me, the tipping point came on a three-hour drive to Visalia, California. Yes, Visalia—the Fresno of Fresno-adjacent towns (Fres-yes IYKYK), known for its scenic nothingness and, apparently, a healthy supply of the Yellow Fever vaccine. At $350 a shot, no less, because naturally, my insurance doesn’t cover it. This was the first clue that I’d possibly set myself up for an adventure of questionable merit.

While administering my yellow fever shot, the all-knowing doctor switched me from doxycycline to for malaria, insisting in a no-nonsense tone that with a thick Indian accent “fewer pills” would make my life easier. Fewer pills, sure, but not fewer side effects, as I’d soon learn. Malarone, it turns out, pairs exceptionally well with, or causes, an existential crisis, and soon enough I’d be experiencing both at once, courtesy of a bargain first-class ticket to Trinidad that I’d booked in a sleep-deprived haze at 2am when I couldn’t sleep one night.

My day started so promising with a cup of tea and scone.

Lesson #1: Inventing cocktails is an art, but maybe wait for more reliable glassware

Ah, the thrill of cheap flights and late-night impulsiveness. One minute I was daydreaming about a Caribbean getaway filled with beaches and wildlife; the next, I was one click away from turning my Fourth of July into an endurance test disguised as a vacation. I found a first-class seat from California to Port of Spain with a route as labyrinthine as my life choices. A stop in LA, a jaunt to Denver, a layover in Newark, and stops in Guyana, Suriname, and Panama. Not exactly an efficient route to paradise. But I was committed.

The journey started with a flight so turbulent it felt like an amusement park ride. Midwest summer storms have a way of making you question all your decisions while trying not to spill your cocktail—a cocktail I invented on the fly, by the way, by mixing Buffalo Trace and Sprite in a flimsy plastic cup. I figured I could pass the time reading through work proposals for a conference I help to organize. But each jolt reminded me that life really has better hobbies than working in turbulence.

A museum conference session proposal about brining Instagram stories to life that I read during turbulence.

There’s a time and place for creativity, but a flimsy plastic cup mid-flight is hardly the ideal setting for mixology. Save the experimental drinks for solid ground—or at least for when the fasten seatbelt sign is off.

Lesson #2: Lower Your Expectations and You'll Still Be Surprised

By the time I landed in Newark for my red eye to Port of Spain, I was questioning not only my choice to travel but maybe my entire approach to decision-making. "Why am I paying strangers in Guyana for tours I’m not even sure exist?" I texted the Brit, hoping for some reassurance. His response? “You’ll be fine.” That was it. It was somehow oddly comforting to hear this from someone you like and trust, but was also a little short to be the heartening pep talk I was after.

In a moment of clarity, or possibly delirium, I called another friend in California to ask, rhetorically, what I was doing with my life. He said, “I’ve wondered that about you too,” which, while technically an answer, wasn’t the one I wanted to hear. But there was no turning back now. I was already too deep into this travel farce.

Finally, I boarded my red eye, settling in with the faint hope that things might finally smooth out. Wrong. Mid-flight, there was a “Doctor needed onboard” announcement, and before I knew it, we were heading back to Newark, complete with paramedics, a stretcher specifically made for airplane aisles, police, and a guy escorted off in handcuffs. If this was the universe’s way of throwing up a red flag. I began changing and canceling plans so that I wouldn't have to fly into the Amazon jungle on a tiny Guyana Airlines plane even though I'd be missing out on a waterfall/bromeliad/tadpole experience recently made famous by a visit from Prince Harry, as well as Planet Earth narrated by Oprah that no one seemed to enjoy because they missed David Attenborough.

I grabbed a seat and propped my legs up on my roller carry-on with the hope of getting some shut eye. No dice. Five hours and a Xanax later, we took off again. By this point, I was more zombie than human. When we finally touched down in Trinidad, I stumbled off the plane like a survivor of some airborne ordeal. Naturally, I’d hoped my island tour would be canceled by now, allowing me to head straight to my hotel to catch some sleep. No such luck. My guide, Xena (yes, Xena), was waiting. In my exhausted state thanks to a combination of prescription drugs and bourbon, I imagined her as some Lucy Lawless warrior princess of travel, here to shepherd me through the rest of my absurd journey.

Midnight in Newark International. C is not for Chic at this time of night like United's sign communicates. I'm unsure which, chairs or tables, serve as better airport beds.

Xena suggested we start with a detour to Rituals Coffee House—a local spot where coffee meets hipster aspirations. I offered to buy her a coffee as an apology for the seven-hour airport wait she’d endured. She politely declined, sparing herself an overpriced mochaccino. At the time, I was trying to figure out if Trinidadian currency used the same dollar sign as in the U.S., because if not, coffee prices here were bordering on daylight robbery.

My mochaccino was not $25 USD.

As we drove, I marveled at the neighborhood around the coffee shop, a striking mix of colonial architecture and Caribbean vibrance. I take drive-by shots of stately mansions, soaking in the island’s unique flavor even as my eyelids threaten to close for good. Xena confirmed that no, the dollar sign isn’t the same. And that, at least, felt like a small win.

Trinidad and Tobago, a twin-island nation in the Caribbean, has a vibrant history shaped by diverse influences from the indigenous peoples, European colonizers, African slaves, and Indian indentured laborers. Initially inhabited by the indigenous Arawak and Carib people, the islands were claimed by Christopher Columbus for Spain in 1498. For over 300 years, Trinidad remained a Spanish colony, though by the late 18th century, it saw an influx of French settlers. The British seized Trinidad in 1797, while Tobago changed hands multiple times between the Dutch, French, and British before finally becoming a British colony in 1814. The abolition of slavery in the 1830s led to the importation of indentured laborers from India, which contributed significantly to the cultural tapestry of the islands. In 1962, Trinidad and Tobago achieved independence, later becoming a republic in 1976. Today, the country is known for its vibrant Carnival, calypso music, and rich multicultural heritage.

One of the mansions has a history steeped in many people’s favorite drinks. Angostura bitters, the iconic herbal mix, was invented in the early 19th century by Dr. Johann Gottlieb Benjamin Siegert, a German physician who served as Surgeon General for Simon Bolívar’s armies in Venezuela. Seeking to create a medicinal tonic to alleviate soldiers’ stomach ailments and digestive issues, Siegert experimented with local botanicals and eventually developed the formula for Angostura bitters in 1824 in the town of Angostura (now Ciudad Bolívar). The bitters quickly gained popularity beyond the military for their purported health benefits and distinctive flavor, and by the mid-1800s, they were being exported internationally. The Siegert family moved production to Trinidad in 1875, where Angostura bitters became a staple in Caribbean and global cocktails. With its signature oversized label and potent blend of herbs and spices, Angostura bitters remains one of the most recognizable and enduring ingredients in mixology, adding depth and complexity to drinks and cuisine worldwide, including my favorite drink, the Manhattan.

Nothing to see here except a stately mansion.

Our next stop was Fort George, an old British outpost perched on a hill. The historical military fort offers stunning views of the Caribbean Sea and the Gulf of Paria. Built in 1804 by British Governor Sir Thomas Hislop, it was initially intended to protect the island from potential invasions by the French and Spanish. Though Fort George never actually saw combat, it served as a vital defense outpost during times of tension in the Caribbean. Its strategic vantage point allows visitors to see the sprawling city below, the coast, and even, on clear days, Venezuela in the distance. Today, Fort George is a popular destination for history enthusiasts and travelers alike, where preserved cannons, prison cells, and officer quarters serve as reminders of its colonial past, blending history with breathtaking natural beauty.

The fort felt like an oasis on this day —a reprieve from the recycled air of airports and the stale funk of my own travel-worn clothes. Local kids raced around while I enjoyed the fresh sea breeze. For a moment, I almost felt human again.

When you can see Venezuela (barely) from your window if you live at Fort George, Trinidad.

Then there was Maracas Bay, home to Trinidad’s famous Shark & Bake sandwich. Shark and Bake is a beloved street food and culinary icon in Trinidad and Tobago, particularly popular at Maracas Bay, where beachgoers and locals alike line up to savor this unique dish. The “bake” is a deep-fried doughy bread that’s crisp on the outside and fluffy on the inside, sliced open and filled with tender, seasoned shark meat (though other types of fish are now commonly used due to sustainability concerns). What makes Shark and Bake truly memorable is the variety of toppings and sauces offered, allowing diners to customize their sandwich with choices like pepper sauce, tamarind, garlic, coleslaw, and pineapple. Originating as a humble beach snack, Shark and Bake has become a symbol of Trinidadian culinary creativity and resilience, embodying the fusion of flavors that characterize the nation’s diverse culture.

I’d seen the dish on a travel show while flipping through channels one day and was excited to try it, but in a last-ditch attempt to act ethically, I ordered Kingfish & Bake instead, assuming it was a sustainable choice. It tasted... well, like fish. I dissected the sandwich once I wondered if this was a country whose water would agree with my stomach but removing any raw vegetables.

Sometimes you get exactly what you order, which in this case was an overpriced and uninspiring sandwich.

There's a reason why the beach at Maracas Bay is famous. Though, perhaps I should've paid attention to the red flags.

By now, the beach feels too idyllic to match my worn-out attire. Noticing my halfhearted attempts to enjoy the sand in jeans, Xena kindly offers to drive me to my hotel. I accept eagerly, my one ambition now to peel off the clothes I’ve been wearing for days and fall into a cold, air-conditioned stupor.

Upon reaching the Hilton, I thanked Xena, dragging myself inside and flopping onto the bed with the kind of dramatic exhaustion reserved for people who’ve grossly overestimated their stamina. I tore off my clothes, laid directly below the air conditioning unit, and passed out.

There's no such thing as a bad time at a poolside bar.

When I awoke, I decided that I didn't feel like exploring Port of Spain. Instead, I sat next to the Hilton's pool, drank beer, and watched day turn into night.

When things seem like they can’t get any worse—like a delayed redeye or an in-flight medical emergency—sometimes the universe likes to add a plot twist. Expecting smooth sailing when embarking on a chaotic journey may lead to disappointment; sometimes, all you can do is ride the absurd wave.

Lesson #3: Sometimes You Get Exactly What You Bite Off—and It’s Just Enough

As the days go by, I come to learn that Xena is indeed a warrior, handling this chaotic landscape and terrible traffic with ease that only someone who's had their fair share of life experiences could do. I, on the other hand, am left grappling with the sheer thrill and absurdity of this venture. Along the way, I learn that Malarone can cause anxiety—an insight that perfectly explains my mindset on this trip. For all my preparation, I’m just another traveler adrift in the Caribbean, realizing too late that maybe this wasn’t my brightest idea.

Still, there's a kind of charm in realizing that life doesn't always go as planned. Sometimes, the best trips are the ones that throw you off course, where you end up in places you didn't expect, navigating situations that leave you questioning your own sanity. It’s these misadventures that remind me why I started solo traveling in the first place: to see how far I can stretch the limits of what I think I can handle.

I’d like to say I’ve learned my lesson. However, to this day, I still book flights on those late-night Google sprees, convinced that maybe this time will be different. And they have been. Nothing could prepare me for what would come on the rest of this Caribbean Basin adventure.