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The Seasonal Primer to St. Thomas

St. Thomas Primer

Long Bay, Charlotte Amalie, St. Thomas

(I took this picture on my lunch break)

Do you want to spend a ‘winter’ on the beach, drink in hand, and leave at the end of the season with way more money than you came with? (Not to mention a great tan) No, seriously, do you? Because you can and other than the part where you hold your breath, close your eyes, and click the button to buy the ticket, it’s actually surprisingly easy. This is the Seasonal Primer to St. Thomas and I’m going to tell you how to do all that and more. First, let me introduce you to Jessica, Michael, and Virginia, who will be helping me talk about the island we called home…

Introduction - Jessica
Introduction - Michael
Introduction - Virginia

I move on to another day,

to a whole new town with a whole new way.

-Modest Mouse

Every Seasonal has a different reason for traveling to any given place.  Sometimes its money, sometimes it’s the weather, and there are equal amounts of time spent following someone or running from something.  I heard St. Thomas frequently called the Island of Misfit Toys and it absolutely fits that title. People have come from all walks of life to be there. That’s because the dream of living, not just vacationing, in tropical paradise is universal.


In St. Thomas, I woke up to the sunshine pouring through my bedroom sliding glass door, walked out onto the porch overlooking the beautiful azure waves, walked a block for eggs benedict and bottomless Irish coffee, then walked another block and spent the afternoon on the beach. I’m not talking about Myrtle, Virginia, or Venice Beach, I’m talking about a beach where it’s just you and your friends and maybe a couple other groups a hundred yards away. A beach where you can play your own music and actually hear it. A beach where you can bring all the booze you want and never have to worry about some plastic-badge on a beach-combing Segway coming by and scolding you through five-dollar reflective shades. A beach where everyone looks like they could be in a beer commercial and not a “Where Are They Now?” episode featuring people who eat McDonald’s twice a day.

St. Thomas Primer

Haulover Cut, Frenchtown, St. Thomas

(This was the view from my porch every morning)

There are plenty of these great spots to choose from on St. Thomas. Magen’s Bay is always included in lists of the top ten beaches in the world.  The locals will tell you the best beach is indisputably Santa Maria Bay. I can tell you the best snorkeling I’ve found is in the cold distant waters at Sapphire Beach. Hassel Island has a great hiking trail that takes you through 200 year old ruins of British forts. St. John has over thirty hiking trails featuring waterfalls, petroglyphs, ruins, mangrove forests, and more great snorkeling spots. Like to party and dance on the weekends? Good, so does everyone else down there, exhibit A would be the gratuitous Carnivale celebration.


The price for living in such a beautiful place must be a terrible job, right? Wrong. With a plethora of great beaches comes a job market that allows for plenty of time to be out on the water. Maybe the Seasonal in your heart is drawn to working on a catamaran or giving night-time glass-bottomed kayak tours? Both are possible in St. Thomas. When I first got there, a few places told me they’d hire me on the spot if I was a certified diving instructor. You could be the tan, hard-body giving the snorkel tours to the young, affluent divorcee and his/her hot friends. Also, there’s such a thing as flyboarding, where you ride a board in the ocean propelled by water jets and get paid for it. Your Caribbean dream job is down there somewhere. So why did Virginia, Michael, and Jessica go to St. Thomas?

Why St. Thomas? - Jessica
Why St. Thomas? - Michael
Why St. Thomas? - Virginia

Don’t think about all those things you feel,

Just be glad to be here.

-FC Kahuna

So how do you get to St. Thomas? Well, there’s always taking a cruise ship and just not getting back on once you’ve made it to the Virgin Islands, but the cheapest way to get to St. Thomas is by plane. Sometime in the middle of November, prices range from $160 out of New York to $180 out of Chicago to $225 out of Denver. So, about three days’ worth of work at minimum wage.


Is the middle of November the right time to go? I went in mid-October and while I definitely think I was too early to make the big bucks, I also found a job extremely easily. If you come later in the season, you’ll be there when more money is flowing but the jobs might be harder to get. You’ll have to decide on your own how confident you are in your resume. Always keep in mind; if you can get to work on time and pass the first drug test, you’re way ahead of the competition.


Before we get into the details, let’s hear the advice Michael, Jessica, and Virginia have for Seasonals who are coming down to St. Thomas...

Seasonal Advice - Jessica
Seasonal Advice - Michael
Seasonal Advice - Virginia

Echoing Michael’s advice, I think life in St. Thomas is a hundred times better if you have a car and a place to live as soon as you get on the island. Why is a car so necessary? Well, on the island you have two options when it comes to public transportation: Safaris and cabs. A safari is a pickup truck with the bed converted into about five benches that seat five people each. (If you’ve ever been to Thailand, you’re familiar with song-tow, safaris are more like hah-tow) Riders catch the safari at predetermined stops and pay a dollar or two to get to another predetermined stop. Safaris are amazing if you’re not in a hurry and you live, work, and only want to go somewhere on their route between the hours of 9am and 6pm, Monday through Saturday. The cabs in St. Thomas are a very personal experience. Everyone has “their” cab driver that will pick them up anywhere at any time. Even if you get a car, you need to find “your” cab driver. Make good with them. They will get you out of at least a couple drunken, “how did I get here” nights. They keep their fingers on the pulse of the island and collect all the best gossip. All this comes at a high price, however.

St. Thomas Primer

A real life St. Thomas safari

When I went, I did the kamikaze approach, I flew to the island knowing nothing and no one, and while it worked out for me, there’s a much better way to go and that’s by preparing. A working car in St. Thomas pays for itself over the course of the season. A working car on St. Thomas Craigslist is between $2,000 and $3,000. If you want something that doesn’t make you grimace when you see it every morning, maybe $4,500.


There’s also the option of renting a car. Many established people on the island have two or three cars they keep in working order and rent to people for $400-$600 a month. I think this is a better option to buying because it’s cheaper if you’re only staying the season and there’s a much better chance the car doesn’t have any problems. If you don’t quickly find someone who rents, there are always the chain rental car businesses, but they charge about $500-$700 a month.


Finding a place to live can be a little more complicated. On Craigslist, you’ll find a normal place runs at about $700 a month per person in St. Thomas. If you’re going as a couple or don’t mind sharing a room, that’s going to be a bit less. If you want a respectable place you can bring friends back to, that’s going to be a bit more.


As for where you should live, there are a few options. The North Side is going to have the best views but be more expensive. Frenchman’s Bay is going to be in the middle of everywhere you want to go and the prices are decent. Frenchtown was my favorite place to live, it has the best nightlife and the prices are great. Red Hook and the east side are good if you work over there or want to snorkel every day but it’s a longer drive into Charlotte Amalie and the apartments are hit or miss.

St. Thomas Primer

Lerkenlund, St. Thomas

(The view of Magen's Bay from my porch on the North Side)

One of my first questions I asked the locals was, “where do you buy your food?” If you don’t care about food and want to eat Wendy’s for every meal, go for it. You’ll save a lot of money which can then go to your hospital bills. If you have your priorities in line, however, you’ll want to know where to find the good stuff. There are a few farmer’s markets and local options to be found but work schedules and scarce availability usually rule those out quickly. There are two Pueblos, which are your run of the mill grocery store. The bigger one is across the street from Yacht Haven Grande, the smaller near Crown Bay. The better choice would be Cost U Less in Market Square East. There’s a supermarket in Tutu as well. If you’re looking for more of a Whole Foods/Trader Joe’s experience, The Fruit Bowl in Estate Thomas is your best bet. Walk into each one, you’ll know which one you prefer.


A car, place to live, and food in the fridge is great, but the goal is to not only survive but leave with way more money than you came with. What’s the job market look like? If you’re scuba certified or have your captain’s license, prospective employers will smell you getting of the plane. That’ll be no problem. On the other side of the pay spectrum, if you just want to rent out snorkels, beach chairs, and boats while hanging on the beach in your board shorts, all you have to do is find a beach, inquire with the right pop-up rental establishment, and show up on time for the first week or two.

St. Thomas Primer

If you're a boat captain, snorkel guide, deckhand, etc...

This is your office

For those of us who lack special skills but have higher financial ambition, finding a job takes a bit of effort. To be a catamaran deckhand, stand-up paddleboard guide, snorkel tour guide, or any other picturesque, awesome, brag-to-your-friends-back-home Caribbean job, you’ll have to hustle, be persistent, and have a bit of luck. These are the jobs everybody is going for and as you can imagine, most people who get them decide to stay year round, not just for a season. You’ll have to find and then talk to the right people, say the right things, and be able to hear ‘no’ at least five times before you expect to hear your first ‘yes’. Scoring the dream job isn’t impossible but to most people it’s going to seem like it. Most people prefer the easy route. In St. Thomas, just like everywhere else in the world, there’s always an easy route in the job market.


Most of the available jobs, along with most of the money, are in the service industry.  Servers and bartenders, cooks, and baristas. I’ve found there to be a rabid clique-like culture among the lifers and a fun but aloof attitude toward most Seasonals trying their hand at the island life for the first time. Sort of like the staff of any Applebees or T.G.I.Friday’s but with more alcoholism.


Turnover can be very high in some restaurants and most of the managers would rather take their chances on someone new to the island than one of the regulars in the rotating bullpen. Keep in mind, most of your friends for the first month or two are going to be the people you work with. If you’re high energy, find the place with a great night scene. If you prefer a quieter weekend, try one of the places that do better during the day. If you don’t like people or like smoking weed more than people, apply at one of the pizza joints. Getting a job will probably be one of the easier things you do on the island.


How much can you expect to make? I usually worked eight shifts in a week, taking one day off, and I expected to average $150 a shift. This was at one of the above average restaurants. I knew servers and bartenders who expected to make $300 a shift. I also knew guys on the beach renting boats that made $125 a day. How much you want and do make is ultimately dependent on how bad you want it. The great thing about St. Thomas was that everyone who wanted that life could make it work for them.

Don’t worry

About a thing

Cause every little thing

Is gonna be alright

-Bob Marley

Now that your survival in the tropical paradise is taken care of, what can you expect out of your free time in St. Thomas? Let’s ask Jessica, Michael, and Virginia what they found to be surprisingly awesome about St. Thomas.

Suprisingly Awesome - Jessica
Surprisingly Awesome - Michael
Surprisingly Awesome - Virginia

When it comes to the beaches, enough has been said all over the internet about Magen’s Bay. It’s great, go see it, you’ll enjoy it. But as I said earlier, all the locals say Santa Maria Bay is the best. I spent most of my time on the deserted side of Emerald Beach. Brewers Beach is right next to the University and has some great snorkeling. Sapphire Beach has great snorkeling too; I swam alongside some sea turtles and saw two different kinds of rays among the coral there. Everyone you meet will seemingly have a different ‘spot’ or island secret to let you in on. People who live in St. Thomas year round want you to think it’s awesome. They will go to great lengths to get you to envy where they live. This benefits the new person.


While your new crew is telling you where to go, ask them where not to go, as well. The thing that surprised me most, and Jessica touched on this as well, is how much crime there is in St. Thomas. One of the most important things I can tell you is, do not go to a beach after sundown without a large group. After the sun goes down, the beaches belong to the locals, respect that. My first week or so, I didn’t have a care in the world down there. After hearing some gunshots, that changed. When I got mugged at gunpoint, the island began to feel like a prison for me.


Luckily, I had some great friends at that point who showed me the error of my ways. I found out where I shouldn’t go. It was surprisingly quick how much my quality of life improved. I realized the island and the people on it are amazing and beautiful. My last two months were a blast. And after arriving with about $600, I left with enough money to go to Thailand for six weeks, spend a lazy month and a half in the Midwest, and then go to Alaska for the summer with a couple grand leftover. I would call that a successful season. I asked Virginia, Jessica, and Michael what needed to happen for them to have a successful season…

Successful Season - Jessica
Successful Season - Michael
Successful Season - Virginia

A variant on all this, and something I would say to keep in mind during the first few weeks, is the option of staying and working on St. John. Just an island over, everywhere I went on St. John was fun and beautiful. There’s enough work on St. John, the problem I found and ultimately the reason I didn’t spend my season there is that the housing was too scarce. Maybe I just had bad luck, but I think, and from the people I’ve talked to, if St. John is a possibility, absolutely pursue it. When compared to St. Thomas, there’s less crime, it’s more beautiful, and there’s a smaller social sphere. It may not have the wild nightlife but for some people that can be a positive.

Somewhere beyond the sea

Somewhere waiting for me

-Bobby Darin

I’ve spoken vaguely here and there, and one of my biggest problems with do-it-yourself articles is they don’t spell out the exact steps I need to take. To fix that for you and myself, I’ve created a very specific step-by-step quick template that you can follow or cherry pick from as you see fit.


Book your ticket for the beginning or middle of the week. A weekend is going to cost you extra money and your first weekend in town is going to be a lot of waiting and watching your bank account dwindle. When you fly into Cyril E. King international, take one of the big van taxis into Charlotte Amalie, they’re cheap and you’ll be with other people just arriving. Talk to everyone that looks like they might have information for you or that you might get along with. Make friends quickly and get contact information. Book your first night or nights at Miller Manor. Talk to the owners, Harry and Marg, to get an idea of where people are finding work. They have long-term renters there that work at almost all the restaurants and bars, so they have the inside scoop.

St. Thomas Primer

The view from Miller Manor

Leave Miller Manor early in the morning and come back before nightfall. It’s in kind of a sketchy part of town but if you’re mildly street-smart you’ll know how to deal with it. It’s also one of the closest places to Frenchtown which is where you’ll want to spend your first couple nights socializing. While in Frenchtown, look for Rum Shandy and get friendly with the bartenders and owners. Jeremy, Laura, George, and Colleen will be one of your best sources of information when it comes to open places to stay and what to expect from the job market. It just so happens that Rum Shandy is also the coolest bar on the island. They have cornhole and kickball leagues and the crowd you want to hang out with hangs out at Rum Shandy.


In the morning and throughout the day, be looking for a job or checking out potential apartments. Visit every restaurant and bar in Yacht Haven Grande, then Frenchtown, and then make your way to Red Hook. Apply to jobs like you’ve got three hungry kids back home and your boo’s ex is better looking than you. Put relevant (as opposed to irrelevant) skills and past jobs on your applications. Put one of your friends as the second reference but put that the relationship is business. Make sure they know a call is coming and don’t make it the friend that gets sweaty hands when talking to your grandparents. Make it your friend that pulls ass whenever they want it. (Thanks again, James)

St. Thomas Primer

Look for all the context clues of whether it’s a good job situation or a shitty job situation. DO NOT settle for a shitty job situation. I repeat…DO NOT settle for a shitty job situation. You left one back home for a reason.


While you’ve been applying to jobs and looking at apartments, you’ve been talking to everyone that looks cool, right? Good. Those people know where to get a car. Use them. Use everyone. A beer or a shot of Grand Marnier (Why is Grand Marnier the St. Thomas bartenders’ shot of choice? I never found out) has immense power of persuasion on this island.


Now you’re starting your second week. You have a couple job opportunities, you are starting to get the car situation figured out, and you’ve found an apartment. Go to Barefoot Buddha and get something to drink. Sit on the couches. Imagine how your life would be in every combination of job and car and house. Sit there for an hour or two if you have to. Get a PO Box there. Your mail will be consistently on time and you’ll have an excuse to go to Barefoot Buddha. (As if you’ll need one)


When you have all your options in front of you and you’ve thought about the best course of action, strike. Strike hard and strike fast. At the end of your second week, you have a job, a car, an apartment, new friends, and you’re living the Caribbean dream. Buckle down into the work hard, play hard mindset. Yes, it’s annoying and anyone that says it out loud is a douchebag, but it’s what you have to do until you recoup your funds.


Your second weekend in town, get a couple of your new friends together for brunch at Bella Blu. Drink more Irish Coffees or Mimosas than you should. Then go beach hopping. When crashing a resort’s beach, look for one of their striped towels. These towels are golden tickets. With the exclusive striped towels, you’ll be invisible to the gremlins that roam the beach charging non-paying guests for beach chairs and pool access. End up at XO Bistro for wine and dinner. Make plans to see The Baths on Virgin Gorda. Let St. Thomas swallow you whole.


If you’ve never done anything like this, it can seem like an intimidating leap of faith. Going to a new place and attempting to do what seems impossible can be a paralyzing thought. St. Thomas isn’t the easiest place to start your Seasonal life, but it’s far from the most difficult. If you want to live where other people vacation, you’ll make it work, and when you stop looking for the safety net before you jump, you’ll come to find this lifestyle is easier than you ever imagined. Well, after you’ve read the Seasonal Primer, that is.



Written by Joey Rovinsky

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