Anguilla: Where the Roads Have No Signs (and Neither Does Life)

Dutch islands seem to like to have weekly fireworks shows for no reason.

It’s always the fireworks, isn’t it? They explode overhead like some cosmic inside joke that I’m clearly not in on, reminding me that peace and quiet are just myths—things you read about in yoga brochures, but never actually experience, particularly not on Dutch Caribbean party islands. Tonight, as the pyrotechnics light up the sky with their predictable drama, I’m in the middle of a slightly emotional conversation with the Brit. A man of few expressive feelings until after a solid lineup of St. Barts cocktails, he suddenly seems... vulnerable. Or maybe that’s just the rum talking. Either way, sleep is a lost cause. I’m tossing and turning, already wondering how I'll feel during his departure, and imagining a future where “right person, wrong place” would become my new autobiography title

There’s something sobering about realizing that an incredible relationship can still be no match for time zones, work schedules, and the logistical nightmare of adult life. You can meet the right person in the wrong place, and it still might not work out. It’s the kind of grown-up realization that makes me long for the days when the hardest decision was whether I wanted Taco Bell for lunch.

The view of the sunrise over Maho Beach from our room.

We wake at dawn, because of course there’s a boat to catch, and sip our coffee while the sun rises over Maho Beach. Ever the adventurers, we set off for Anguilla, confident that this time we know where the dock is. Spoiler alert: we don’t. It’s not exactly clear where to park, because naturally, it wouldn’t be. But hey, no hiccups with immigration this time, and the officer kindly corrects my pronunciation of “Anguilla.” Apparently, my attempt at Spanish isn’t appreciated here.

The boat ride to Anguilla is smooth enough, and soon we’re through UK immigration, standing in front of a car rental place that inexplicably doubles as a hot sauce shop. Naturally, I can’t resist buying a bottle. Nothing says “I’m about to drive on the left side of the road” like clinging to a bottle of hot sauce. Armed with my new hot pink Anguilla driver’s license, I slide into the rental car, only slightly panicked. The Brit, never calm when I'm driving, gives me a pair of his cheap plastic gift-with-purchase Veuve Clicquot sunglasses because I forgot mine.

Legal driver in Anguilla without a test.

Anguilla, the laid-back cousin in the Caribbean family, was first settled by Indigenous peoples before being “discovered” by European explorers in the 1600s. In classic colonial fashion, the British swooped in and claimed it, leading to a few centuries of political limbo, a little revolution here, some territorial reconfiguration there, proving the island has both the chill vibes and the rebellious streak to match. Today, it’s known for pristine beaches, low-key luxury, and a population that’s just as likely to hand you a beer as they are to correct your pronunciation of “Anguilla,” apparently.

As we set off from the beachside rental company/hot sauce store, I’m chanting to myself: “Left, left, left, stay to the left.” It’s a mantra, a survival strategy around roundabouts, and somehow, despite missed turns and mysterious dead ends, we find our way to a beach so perfect it feels like a setup. It’s deserted, pristine, the kind of place where nothing bad could ever happen—except in horror movies, of course. But instead of terror, we spend the day in bliss, alternating between naps, drinks, and slathering on sunscreen like the responsible adults we pretend to be.

My best Daniel Craig

Eventually, it’s time to head back. After a few sun-soaked hours, we return the car and make our way to the dock for the short ride back to Sint Maarten. As we boat through Simpson Bay Lagoon, we pass a sunken boat, its hull graffitied with the words: “Life is too short to sink completely.”

The simple message hits harder than I expect. There it is, scrawled on a half-submerged wreck, offering up the kind of wisdom you don’t even realize you need. It stays with me all day, and honestly, even years later, whenever things go off the rails, that boat pops into my head like some half-drowned oracle, reminding me: "Hey, life’s a mess, but you don’t have to go down with the ship."

After dropping the Brit off at the airport, I head back to our construction-site resort and settle in for a night alone, nursing a sad rum-and-Coke at the mediocre bar. I can’t shake the feeling that this might be the last time I see him. Are we just two ships passing in the night, or is there more to it? In the dim light of Caribbean rum, it’s hard to say.

The next morning, I sit on the hotel balcony with my coffee, trying to process the whirlwind of the last few days. I catch up on work email and then flip open my book, Eat Pray Love, and land on a passage where Elizabeth Gilbert writes: “I feel about travel the way a happy new mother feels about her impossible, colicky, restless, newborn baby—I just don’t care what it puts me through. Because I adore it. Because it’s mine.”

When the thing you do is exactly what you're not supposed to do.

And there it is—my own personal rum-soaked revelation. Travel is messy, inconvenient, and exhausting, but it’s also exhilarating, full of unexpected moments, like finding a message of hope on a sunken boat. It reminds me that, no matter how many wrong turns we take or how chaotic life gets, we just have to keep going. Life is too short to sink completely, after all.

I try to catch more photos on Maho Beach before packing up the rental car and heading to the airport dealership. I catch a glimpse of the tagline on the license plate, “The Friendly Island.” I ponder the people I've met, the experiences I've had, and how Hurricane Irma impacted my short holiday in so many ways.

As I board my Copa Airlines flight to Panama, I glance out the window and see a crowd gathered on Maho Beach, waiting for my plane to blast them with the jet engine. I smile, realizing it’s someone else’s turn to be blown away—quite literally.