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My Own Rum Diary In St. Thomas

Roam Chronicles

What the fuck am I doing here?

It was a question I had been asking myself a lot lately.  Whether I was at work unloading trucks in back of Bolongo Bay Resort, hitchhiking around the island because my jeep was broken again, or surfing out at Hull bay, a sense of head-shaking wonder was pretty much a permanent state of mind these days.

I had washed up in St. Thomas after months riding out a particularly wet spring in New York.  Between jobs and in a funk that matched the weather, I felt like I hadn’t been outside my 400 square foot cage in months although it had probably just been days.  

I justified my relocation to the Virgin Islands armed with the knowledge that tax breaks given by the federal government to encourage businesses to relocate to the islands were mainly taken advantage of by hedge funds and money managers, just the types of criminals that I had become accustomed to working with after years in the spy-novel worthy shadiness of the commodity brokerage world.  On paper, it was actually a good idea, although greeted skeptically by pretty much everyone I repeated the story to.  After all, how many other people with securities licenses and a decade of finance experience were floating around down there?  

Most people just shook their heads.  Uh huh.  

As it turned out, and a surprise to absolutely no one, the vast majority of these stand-up citizens of the financial world were scamming the system, following the absolute minimum letter of the law and not the spirit, employing house-keepers for empty mansions, drivers for yachts used once a year, dog walkers, pool cleaners, anyone other than a professional, all while saving over 90% of their federal taxes in the meantime.  Within a few years the government would shut the loophole and the absentee bosses would move on to the next scam.

People were used to my schemes at this point.  One of my friends explicitly and sarcastically said, ‘How many more going away parties are we throwing for this guy?’  What could I say, I like to leave and I didn’t need anyone to make a big deal out of it.  I was like an old penny who would disappear to foreign lands only to turn back up once the money had run out or the half baked plan had just run its natural course. 

Maybe this was just what happened when you didn’t have much of a plan to begin with but your manic bi-polar personality continually shape-shifted between being addicted to the money and action and drugs of Wall St. and the introverted recuperative power of disappearing to the tropics with nothing but a surfboard and a backpack, living on beans and rice and a few dollars a day and trading the stiletto armored girls of New York with their much friendlier colleagues on the backpacker trail.

Instead of entering the ranks of offshore money movers and tax dodgers, I ended up joining the ranks of seasonal resort help.  Unlike the majority of my other white skinne bretheren in the area, I didn’t end up in a customer facing role at the front of the house, serving pina coladas and imported fish of the day plates to sunburnt oakies and obese manitee-like scuba divers. 

Going Local in St. Thomas

Luckily I ended up managing the warehouse where my daily interactions were with local West Indians who ran the supply chain, delivery drivers, fisherman, produce suppliers.  While most people felt sorry for me back in the rat-infested warehouse, I loved it.  It was the ultimate connection to the local community and quickly separated me from the rest. 

After all, St. Thomas is a small island and in a short time, I couldn’t go to a local beach, or walk through town or even drive down the road without getting honks and waves and in true island fashion, just stopping in the middle of the road, blocking the lanes in both directions, and having a long chat as if we were sipping tea on someones back patio.

Bobo worked with me back in the warehouse.  He has a tall and lanky rastafari who had dreadlocks down to his waist, smelled of weed, and had the friendly, affable laugh of someone not taking things too seriously.  Things were pretty laid back in the warehouse unless one of the local women who ran the kitchen came back looking for something. 

Usually Bobo was nowhere to be found when this happened, some sixth sense allowing him to disappear before they arrived, tooth-sucking and arms waiving and wondering where the strawberries were.  At first, it could be terrifying, but I would come to learn that these confrontations always ended with a big smile and hearty laugh at my expense.

I would see these ladies around the island too and they would tell me the best places to go get fresh produce or the best beachside food truck to grab a salt-fish roti, things the people serving tourists their frozen drinks at the bar never learned.  

Surfing in St. Thomas

St. Thomas isn’t on the well-trodden surf circuit, but not because there isn’t surf.  It’s just that it doesn’t have the consistency of a Costa Rica or the big wave spots of Puerto Rico just a few miles away.  When you’re flying across the ocean with a bag full of boards, you want to get your best chances of grabbing waves, so the Virgin Islands don’t make the list.  Because of this, there’s also nowhere to rent surfboards or anything like that.

But I surfed all the time.

The main surf break on St. Thomas is at Hull Bay, a beautiful secluded beach on the North side of the island.  Hull is mainly populated by Frenchies, local fisherman who descend from French colonials in the Caribbean and are known for being an insular, self-dependent community.  The gist of what I was told when I got to the island was just don’t mess with them and you’ll be fine, but touch their fishing boat and you’ll end up in a trap at the bottom of the reef.  I thought that was reasonable and never had any problems there.

The surf break at Hull Bay is a long but easy half-mile paddle from the beach.  Sitting in the water at Hull Bay is unlike anything I have experienced to this point, the colors, the reef, animals, it’s like being on LSD.  As I ride a wave of the crystal clear blue-green water, watching huge brain corals fly by under my board in streaks of yellow, pink and orange, rainbow explodes over the lush green hills in front of me and a lone grey cloud drifts by further out to sea, raining just right under it but no where else. 

The vibrancy of the colors in the Caribbean is astonishing, overwhelming my senses.  Add to that the experience of riding uncrowded waves and the universal comfort of air, water, rain, all being experienced at the perfect temperature.  I half expect a turtle to pop up its head and start talking to me at any second.  I wouldn’t be surprised, and indeed it would often happen, that you would see reef fish, turtles, whale sharks all in the same session while you look in the aquarium clear water without the need for goggles.

Now, if you look up surfing in St. Thomas, Hull Bay is the place you’ll find most often listed, mostly because it is the easiest to get to, but there are plenty of others.  It is an island after all, offering 360 degrees of swell window and tons of smaller offshore islands to explore.  

There were a couple of other surfers where I worked that had been there for longer than me and so knew the lay of the land a bit.  I also lived next door to a guy who had lived in St. Thomas his whole life and, more importantly, had a boat.

Surfing Botany Bay St. Thomas

 If you look at a map of St. Thomas, you’ll see that the vast majority of the development is on the Eastern two-thirds of the island.  The whole Western third is sparsely populated with some large estates and plenty of shacks in the dense tropical jungle.  This leaves an amazing amount of exploration to be done, despite what you would hear from people who only saw Charlotte Amalie and Megan’s Bay in their quick guided tour when they got of the floating prison known as a cruise ship.

The thing is there aren’t many roads over on that end of the island either, so it can be helpful to explore it from the water.  My neighbor knew a spot that would be breaking in the current swell direction so we went to check it out.  Despite being on an island, I found that hooking up with people who had a boat proved to be difficult.  Expensive and difficult to maintain, boats were just out of reach for most of the itterant restaurant worker crowd I was mixing with, so getting out on one to explore the island and surf breaks that were unreachable to most was a welcome adventure.

Considering Hull Bay rarely had more than a couple of surfers out at any given time, it wasn’t a surprise that we had this clean right point out by Botany Bay to ourselves.  In fact, I would have been surprised, shocked in fact, if it was any other way.  At the end of the day, there just aren’t many surfers in the Virgin Islands.  That’s just not why people are there, and from what I could tell, people were mainly there to drink.

We worked this point for hours with no one out, easily swapping waves when the head-high sets arrived.  Unfortunately, this wouldn’t become a regular thing as my neighbor was susceptible to the same pitfalls of boat ownership as anyone else, expensive gas, broken parts, just couldn’t bother.  Oh well, it happened.

The Sinking Boat

So this led to some other, less well thought out boat exploration as well.  When Rob from the restaurant said he found a guy with a boat I knew it was going to be sketchy, but you don’t move to the Caribbean if you aren’t comfortably with some degree of sketchiness in general.  So we headed out to Caret Bay where this young couple with a little baby crawling around were rolling joints and wake-and-baking to get the day started. 

I didn’t like the scene, although was making a note that this little condo complex by the beach near all of the surf might be a good place to move if my stay here turned long term.  The guy had a small inflatable dinghy with a 25 horsepower outboard, pretty much the industry standard for island hoppers and sailboat cruisers everywhere. 

The difference was that most people use these for the short hop from their mooring to the dock or the beach, not to go explore outer islands while a Category 3 storm is spinning a few hundred miles offshore.  

The swells were massive.  The surf was pounding and closing out the bay in huge walls of white water.  There were three of us plus our surfboards and a few supplies as we nosed the boat towards the waves, the driver sitting in the boat with the engine running and us on each side keeping the boat straight as we waited for a lull in the sets to gun it out. 

Surfers have a good eye for this timing, so we were patient and when we saw our moment, we were on it more than a quick ‘now’.  The driver gunned the engine and we hoped on board and we shot to the outside as the boat labored with our weight.

Beyond the breakers we motored over large rolling swells in the deeper dark blue water, heading north and a bit east towards the Outer Brass Island one of the two uninhabited Brass Islands (Inner and Outer) just offshore, where we hoped to spot a place that might be surfable.  Honestly, this was true surf exploration as I had never experienced it before, riding large storm swells in an undersized boat towards areas not really known for surf.

With the large swells coming from the north, we looked around the South side of Outer Brass to see if the waves were wrapping around anywhere.  We knew the more exposed North side of the island was just getting pounded, much like the bay we had left on the main island. 

We Go Shark Diving There

As we approached the southeast tip of Outer Brass, we could see that waves were breaking in open water out beyond the point so we decided to take a closer look.  It was a bit chaotic, nothing like some Mentawai dream where you pull up to find some point peeling for hundreds of yards without a drop of water out of place.  The waves weren’t even breaking towards the land, but more from east to west as the swells wrapped around the small rock.  

With nowhere to anchor and the surf looking sketchy at best, the owner of the boat said he would just stay with the boat so he could chase us down if the currents started taking us out to sea.  Nice of him, I thought.  Me and Rob jumped in with our boards to paddle in for a closer look.  Peaks were breaking all over the place, so it was hard to pick out exactly the best spot for a line up. 

We instinctively stuck together so that we could keep an eye on eachother and the boat would have an easier time getting us if things got too out of control.  We couldn’t even see the boat when it fell into the trough of the swells, so we kept our heads on a swivel for waves, markings on shore, the boat, and each other.

After a half hour or so of paddling in the swirling mess we decided that we weren’t going to have much luck here, plus our boat driver was waving us over.  Burning gas doing circles in wasn’t really part of the plan, plus he had discovered a small problem which, I thought he was being a bit too calm about.  Our boat was losing air.  

Now, when he said ‘I think the boat is losing a little air’ I was concerned but calm.  When I climbed back into the boat I was no longer calm, at least on the inside, despite remaining so on the outside.  The boat had lost a ton of air. 

Either we had been out in the surf longer than I thought or this thing was losing air fast.  Either way, we needed to get out of there and back onto dry land.  Of course, this was going to mean getting back across the straight between the islands and through that raging whitewater that was closing out Caret Bay. 

I knew that people on this island were crazy, but when I saw the state of the boat I assumed it was a foregone conclusion that we would head back.  Apparently it was actually up for debate as we discussed whether there would be better waves around at Botany Point, where I had surfed from a much bigger and more seaworthy boat previously so knew it would take an hour in this little sinking ship. 

Calmly but firmly I pointed out these facts, also alluding to the good time we were sure to have surfing this rubber raft back into the beach.  Fortunately my knowledge and the obvious fact that the boat was getting worse, not better, as we sat and discussed this won the day.   We headed back to Caret.

Approaching the bay it was clear that things were getting worse, swells bigger, and whitewater was everywhere.  I was a little tougher to judge the lulls between the sets from the outside, looking only at the backs of the waves, so we circled, getting a little closer each time, and kept an eye out to sea for outside sets that might do us in. 

After a long wait we had a sense for the timing and were able to judge a break in the action.  Rob and I were straddled on the sides of the boat, laying forward and holding the surf boards while the driver gunned the engine.  I kept an arm around my board so that I could just bail out and let the white water take me to shore if things went wrong. 

We made it to shore and pulled the limp inflatable craft up on the beach and went to pack up our stuff.   More plans were being made for fixing the boat or taking another shot at it later, or maybe next time heading somewhere else, but I was done with these guys and this boat for now.  I just wanted to get out of there.

Later I would talk about this little misadventure with another buddy of mine from the resort who had been on St. Thomas for a few years.  He didn’t surf, but dove and snorkeled a ton like most of the people there.  When I described the place where we paddled out and tried unsuccessfully to surf, he calmly mentioned that he knew the spot.

 ‘Oh yeah, I went diving there once.  We saw a bunch of sharks.’

Of course he did.

Bob had other good ideas too.  That was one of the things I liked about him, despite the argument that could be made about his judgement, he was just up for anything and was always stoked to try.  Plus he was one of about three other guys I knew who surfed, so when he would call saying he had an idea, or I heard about this spot, I was always game to check it out. 

What else did I have to do anyway.  I’m not sure where he was getting this coconut-vine information, but it was always worth checking out.  I just loved exploring the island, plus, looking for surf generally takes you away from the overrun snorkel and dive spots where the cruise-ship masses were being ferried in droves. 

Our surf exploration was essentially done alone, you never saw anyone else out there.

Night Surfing in St. Thomas

So when he told me he had heard about this place where you can surf a point at night my first reaction of course is ‘heard from who?’, but what actually came of my mouth was, ‘cool, I’ll pick you up latel’.  So I picked him up and we headed to go see what this was all about.

Surfing at night is always a bit, well, tricky.  First it requires getting over the fact that all the aquatic predators are out and about, and you can now see them even less than before if that was even possible. 

Nothing like watching your feet disappear into the inky water not knowing whether there is something huge with its mouth open and rows of teeth pointed at you like that pit on Empire Strikes Back.  Next of course is the waves themselves, silently creeping out of the depths, only to reflect little bits of light that then disappear as soon as the wave takes shape. 

The timing is a bit tough to say the least.

This spot was really amazing though.  There was a rocky point sticking out right in front of a development of apartments, and that development had a nice, well-lit promenade along the water, curving right along to the point. 

Now the lights weren’t right on the water, there was about twenty yards of rocks before the waterline, but they at least shown light from the right direction for surfing, into the waves instead of from behind.  Usually the moon is the only light you get for a good night surf, and if the moonlight is coming from behind, the wave creates a pitch black shadow right where you need to see as it builds and crests.  In this case, as the waves began to build, they picked up the faint yellow light of the lampposts giving us the perfect surf stadium. 

As always we were the only ones out, and we surfed this perfectly lit point for hours in the warm Caribbean water.  Although this did beg the question, Why don’t we come here every night!’  Or more simply, how come we haven’t surfed this little point during the day?

Best not trouble yourself with thoughts like this.  Such is the islands, and holding a grip on sanity requires letting little questions like these go unanswered.  Also, it just showed that for a place that isn’t even on the surf map there was practically endless surf exploration to be done, both in town and out in the uninhabited nooks and crannies of the western end of the island.  

People in St. Thomas don’t surf, and of the ones that do most don’t have a boat.  And then you take that subset and add in the propensity for islanders to settle into their drinks by the early afternoon and you get a really small subset of dedicated surfers who are capable or interested in dawn patrols or sunset surfs.  Very few are out looking for new adventures, new spots, unexplored bays, and points, when Hull Bay isn’t even crowded anyway.  

St. Thomas might not have the consistency of some other places and even with all these options for surf, most people aren’t gong to plan a surf trip here.  After all, you can increase your odds and get better waves in Puerto Rico.  For surfing, the majority of people just aren’t going to use their precious surf trip to go to the Virgin Islands. 

But what this does is leave an island paradise for the locals, the less than one percent of islanders who surf.  Perfect for those who aren’t looking for the massive barrels of Tres Palmas but are just looking to ride waves in warm, clear water, trip out on the incomparable kaleidoscope of colors the Caribbean throws at you, find empty beaches and eclectic little waves, and who are happy just going for a snorkel when it’s flat.

If this sounds like you, this island paradise is there for the taking.  

Think a surf trip to St. Thomas is in your future? Take a look at our Guide to Surfing St. Thomas.

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Written by Roam Chronicles

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