The hilarious people I met on a luxury cruise in the Caribbean

Doctors? Politicians? Celebrities? You might be surprised who you’ll run into while on board.

The Big Five of cruise passengers.

There’s a cruise for everyone. Whether you’re into Disney princesses, climbing mountains, sourdough or Star Trek. There’s even a cruise for people who hate cruising. It’s called a “luxury cruise”. Because who could hate free lobster and champagne?

I spent a week on one such cruise, on board Explora II as she sashayed her way around the Caribbean. It’s billed as a private yacht-esque experience with fine dining, ocean-inspired wellness and European luxury. The buffet-busting, lanyard-wearing hoards are not in attendance. So who is? Who will you find yourself perched next to at the whiskey bar? Or admiring over the sushi counter? Or sharing a session with in the salt cave?

High end cruises attract a particular clientele.

Everyone on a luxury cruise will likely fall into one of the following five categories. The Big 5, if you will, which you’ll find parading all over the ship like big wild cats, only richer and less hairy. 

The Career Consumed  

You don’t have the money for an ocean-view penthouse if you don’t know how to hustle. I learnt that quick-smart from Steve, the crypto trader who made $15K while we were sitting at trivia. In the time it took me to get the answer to ‘what British actor’s alter ego is DJ Big Driis?’ Steve had shuffled around tens of thousands of dollars worth of Binance Coin and come out on top. The answer is Idris Elba, by the way.

Then there was Tina, the fashion designer who would take meetings with local boutique owners when we hit land instead of indulging in shore excursions like the rest of us. “It really is the best way to check in with new clients,” she told me. “Plus it makes the whole cruise a tax deduction.” Were these the most compelling batch of baddies on board? Quite possibly. But the fascination doesn’t end there. 

We think your writer belongs in the Fashion Set.

The Fashion Set

Twelve thousand dollars: the amount I watched one woman drop in roughly 10 minutes at the Cartier store on Deck 4. What, you can’t purchase opulent jewellery within feet of where you sleep? You can on a luxury cruise.

Don’t let the bling blind you from what everyone else is wearing, though. Keep your eyes peeled for the peacocks in diamond-dotted Rolexes and Louis Vuitton sarongs. And their kids, decked out in Gucci tennis shorts and Burberry sunglasses. The sheer affluence of it all. Also, in case you were wondering, $12K got her two watches - one for her son and one for his girlfriend (because she didn’t want her to feel left out).

Alone and loving it on the Atoll pool deck.

The Solo Travellers

A luxe ship entices more solitary travellers than your average cruise. People with extra time, money, or both on their hands who want to spend a few weeks wistfully staring out at the ocean (almost every solo passenger I met was doing more than one cruise back-to-back). Or who simply seemed to function best when left to their own devices. My favourite of the lone wolves was Carl, a German engineer who had visited over 150 countries and who I’d seek out at dinner for the scintillating conversation. He was followed closely by Robert, the burly and uncharacteristically quiet American who would stay in his room all day only to emerge each night to belt out Frank Sinatra at karaoke. Never the twain did meet.

The mystery cruisers found their niches on the Explora.

The Mystery Contingent

This is the most baffling subset; those who feel like they were just dropped onto the ship from above somehow, like fish falling into a forest. For instance, what is the loud British lorry driver doing here? And that journalist wearing H&M? (Okay, that was me.) But also, how is that 19-year-old flight attendant paying for this cruise? It’s like watching an episode of Grand Designs where a worm breeder and a part-time mime have a budget of $7 million. Not since the Bermuda Triangle has the ocean refused to give up the answer to such mysteries.

This cruise was a milestone for big relationship celebrations.

The Special Occasion Society

The farmer and his wife from Wisconsin who were on board to celebrate her 60th birthday. The group of six who flew over from the UK to be there for their friend’s buddymoon. These people ushered their coins together to take the trip of a lifetime. To honour a milestone. To revel in the ritual.  These guys, I get. The anticipation, the luxury, the fact the oysters are free and you can have as many as you want - none of it is lost on them. They were also the people I enjoyed hanging out with the most. Well, except for the cryptobro who bought me a Pepe Coin every time I made him laugh. No one beat that guy. Sure, they’re only worth $0.00005 now, but just wait…  one day I’ll turn them into another luxury cruise.

The writer travelled as a guest of Explora Journeys. 

Originally published as The hilarious people I met on a luxury cruise in the Caribbean