In the depths of winter, knee-deep in a slush puddle, it’s easy to find oneself slipping off into idle daydreams of quitting it all and moving to more hospitable climes. But how does one just walk away, not just from the brown, intractable snow, but also from the high rents, filthy sidewalks and pushy residents of New York?

A few years ago, my girlfriend (now wife) and I took a much-need vacation to Costa Rica. After a few days of living among the sloths, parrots and thick, freshly caught tuna steaks, we jointly came to realize that New York City was a sucker’s game. Why couldn’t we move there, to warm, tuna-rich Esterillos Oeste? So what if we didn’t speak Spanish? We could surely mime our need for visas and jobs with great gusto.

I have seen Captain Ron, like, a million times. What else did I need to know?

But then I had an even better, lazier idea. Why didn’t we just move to the U.S. Virgin Islands instead? There we could reap all the benefits of an itinerant beach bum’s life, with none of the drawbacks of having to learn a new language or getting working papers. I even knew a few people who worked on parasailing boats in St. Thomas part of the year. Another friend, a former roommate, was now semi-permanently in St. Croix. Most importantly, I have seen Captain Ron, like, a million times. What else did I need to know?

Somehow we went from having that harebrained idea to giving our notice at work and looking for St. Thomas apartments on Craigslist. House hunting from afar is difficult under any circumstances. I knew less than nothing about the layout of the island. Bolongo Bay, Charlotte Amalie, Red Hook (they too have one of those). But so long as it was near the beach, what did I care?

A few near-grifts, which had me on the verge of sending payment down to some wily Caribbean real-estate huckster, left me more wary.

Eventually I got in touch with a friend of a friend who lived down there, and he agreed to pick me up when I arrived. (The lady was going to let me, man-style, find a place to live before she flew down.) I arrived one day in January, and he showed up, as promised, with a rum drink brazenly hanging out of his pickup’s window. One of the first lessons of life in the UVI: Everyone drinks and drives. It’s more of an oddity to get in a car not littered with empty beer bottles than vice versa. To my knowledge, though, there isn’t much in the way of automobile deaths. The place is so hilly, the roads so curvy, that it’s difficult to speed even if you want to.

Hangovers seem to be fairly nonexistent down there, perhaps owing to its relation to the equator or a mild toxin in the water.

This guy took me to his place, nicknamed “the Fort,” where he lived with another early twentysomething enjoying his time away from home. And really, it did look like a tree fort, just not in a tree. Technically, it had indoor plumbing, electricity and running water, but if you’ve seen what two young bachelors can do to a normal apartment in the city, you can only imagine what this place was like. When I eventually found a place to live and my wife flew down, we had to stay a few nights at the Fort before we could move in. Some rats got into an open cereal box about five feet from where we were sleeping on a mattress on the floor. Not a few tears were shed, and I began to wonder for the first time if this maybe wasn’t the best idea I’d ever had.

St. Thomas (or “the Rock,” as it’s popularly known) can be a dangerous piece of beach paradise. Downtown Charlotte Amalie, while it boasts some passable bars and shops and restaurants, is not the kind of place you want to find yourself wandering around in after dark. What the island lacks in vehicular manslaughter, it makes up for in the bullet-borne kind.

Red Hook
Outside a bar in Red Hook

There are plenty of less-dangerous hangouts. One bar that I know of reached some kind of agreement with local drug dealers, tacitly allowing them to hawk their wares in exchange for ensuring its not being robbed by other, less synergistically-inclined drug dealers. We often set down in Red Hook, where a lot of restaurant people would hang out after work. XO Bistro, right next to Duffy’s, was a regular spot where we’d go to play dice and sit in the air conditioning. One infamous douche, apparently an incredibly wealthy energy trader who viewed the island as his personal playground, would regularly come in to XO, tip the bartenders enough to ensure he and his entourage would drink for free and be able to do whatever they wanted, and proceed to act like a complete maniac. One time he walked up to a friend and I, looked at us crazily, muttered some drug-addled gibberish, and crushed his wine glass in his hand, cutting the shit out of it in the process. We were less intimidated than annoyed. This is a man who allegedly pissed on his wife in public, a champion of industry and of life. I guess this display of self-violence just meant he liked us?

You really haven’t lived until you have island hopped carrying your own fecal matter.

For those planning on living and working in St. Thomas, I’d recommend buying a car, just something to beat around the island. It’s not an easily walkable place. Dollar “safari” buses are a decent way to get around, and drive in loops that converge at the Tutu Mall, the cultural and economic hub of St. Thomas. Never was a K-Mart more integral to a local economy.

We often took daylong boat trips to the British Virgin Islands. Jost Van Dyke is always a great time, with boats anchored just off the beach and large groups of people sitting around sipping Painkillers (some mixture of orange juice, pineapple, rum, coconut milk and nutmeg). Willie T’s, a large boat permanently moored off of Norman Island, is a popular floating bar that can only be accessed by watercraft. One time I decided to swim, one-armed, from our own boat, using my other arm to bring a six-pack of Bud Light. Leave no beer behind, I always say. It was a heroic effort, if I do say so myself. Unfortunately, they made me dump the beers once I got on board.

Groceries on St. Thomas can be expensive, what with its being an island and all. Milk, fresh vegetables, even water are sold at a premium. Cruzan Rum, on the other hand, is dirt cheap. Fortunately, hangovers seem to be fairly nonexistent down there, perhaps owing to its relation to the equator or a mild toxin in the water (I’m no hangover scientist). One thing you might miss is draft beer. There are only a few places to get it, none better than the Tap Room on St. John. I’ll never take draft beer for granted again.

St. John

Oh, St. John. Nary a weekend would go by without us jumping on the ferry in Red Hook and heading over to the smallest of the UVIs to lie around on its perfect white sand beaches. Much of the island is protected national parkland, and it shows. Kenny Chesney, I think, has a giant compound there. It was also the chosen getaway for Robert Oppenheimer, the father of the atomic bomb. The routine most people settle into, us included, is working on St. Thomas and playing in St. John. It’s a mere 15 minutes away, and more easily fits the idea of tropical getaway.

As an American, you don’t need a work visa in the UVIs, but if you’re doing restaurant work, you will need to get a health card. For us, this required fifty bucks and pooping into a medical cup for the authorities to test for worms, or something. We carried ours from St. Thomas to the nearest testing facility on St. John. I’ll maintain that you really haven’t lived until you have island hopped carrying your own fecal matter.

The upshot of all this poop talk is this: If the dream of quitting your job and moving to a beach paradise sounds too good to be true, that’s because it probably is. Islands are isolated, and you can only sit on the beach for so long. Your body can only process so much rum. There’s no escaping the sun. It’s easy to do for a week or two, but makes for an entirely different living experience. We stayed for six months or so, and after we acclimated to island life, our time in St. Thomas actually did become quite enjoyable. If not for a job offer in San Francisco, we might have stayed much longer. But do yourself a favor and do your homework. Loath as I am to admit it, Captain Ron doesn’t have all the answers.

Spring has sprung, and we are issuing a call to explore new frontiers here on Made Man. Check out Our Guide to Modern Adventure, soak up the inspiration, then get out and blaze your own epic trail.