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Looking to go on a last-second trip to the Caribbean before the Summer ends? We've got the scoop on how to do it on a dime.
August 8, 2019

Caribbean on the Cheap

by The CE Shop Team

Need to Get Away without Burning a Hole in Your Pocket? 

It’s August. You’re stuck at your desk. The hours on the clock slowly trickle away as you patiently wait for the A.C. guy to come and fix the 92.6-degree office-turned-Russian-bathhouse called your office. Worse, you’re just sitting there. Of course you are. All of your clients are out of town, happily relaxing in the cool Rocky Mountains or some breezy island in the Bahamas

Hmmm, sounds like someone else needs to go on a last-second getaway, ASAP. But how does one do that without breaking the bank? 

Strapped with only $1,500, we sent The CE Shop’s Undercover Investigative Vacation Team to the deep, dark trenches of the Google search to find the cheapest way to get you out of that sweatbox and onto a sunny beach in the Caribbean.

1) Choose a Destination

According to analytics, searching “Cheap Caribbean Destinations” is one of the more popular keyword phrases, so let’s start with that. Before we type that in, we’re going to have to make assumptions and presume, due to population density, you are somewhere in the New York Tri-County area. This gives us a plethora of options since there are three different airports in the area.

We Google the keyword phrase and come across a U.S. News article “Top-Ten Best Cheap Caribbean Vacations”. We checked their “methodology” for determining this list and, after some subtle debating, accept this ranking system as valid. Of their top-ten list, Curacao and Turks and Caicos seem to be the easiest locations to get to. However, this is a last-second flight. The majority of flights to those happening locations are already booked. We’re going to need to find a less popular island. So, after another quick search, we uncover the beautiful island of Saint Thomas in the U.S. Virgin Islands. It’s the Caribbean. Every island’s the same, right?

2) Find a Flight

Okay, so in this process we’re going to try and find the cheapest flight possible. Quality, luxury, and comfort? Throw those meaningless attributes out the window. We need to get you there by any means necessary––even if that means strapping you onto the side of a 757 Boeing jet. Remember, the ride there requires only a few hours of your time. In other words, you’ll survive. 

Let’s see. First we Google “Cheap Flights August 22nd”...and Holy Toledo, we just found you a flight on American Airlines for just $375. Spirit Airlines came in a close second, but they charge out the wazoo for even a carry-on. American Airlines will be just fine for your precious tuchus. 

TOTAL COST: $375 Flight + $40 Tax = $415

3) Find a Hotel

Unlike your flight, we want you to live in (moderate) luxury. So, only 4-star hotels near the beach will suffice. We type in “Saint Thomas Hotels 4-star cheap” and, after some date-changing, we come across two hotels: Bunker Hill Hotel and Galleon House. The Galleon House does not quite meet our requirements––more or less because of their website design––so we choose the Bunker Hill Hotel. Wait, let’s check the reviews. Alright, they’re good (enough). We just booked you a room for $96 for 4 nights. Now let’s think about how arrangements.

TOTAL COST: $415 + $30 Cab Ride (To and From Airport) + $384 (Hotel) = $829

4) Meal Plan

Meal planning for a vacation probably does not sound ideal, but neither does booking a last-second trip to the Caribbean with only $1,500 (“You need to plan better. Why are you so much like your mother,” some grandma in Boca Raton is shouting). 

With a $60/day stipend, we suggest sacrificing some meals via a quick supermarket shopping trip while splurging on others. Check out near-by establishments Savan Grocery, Muhsen Supermarket, and Moe’s Fresh Market Waterfront. There you’ll be able to get quality, but inexpensive, food staples for supplanting most of your breakfasts and lunches in exchange for splurging on hearty, fresh Caribbean meals and tropical drinks. 

For awesome foods at relatively fair prices, Google “cheap foods near bunker hill hotel saint thomas”. There you’ll find all the amazing foods of this Caribbean island that are within walking distance of your hotel. 

TOTAL COST: $829 + $240* (Meals and Supermarkets) = $1,069

*Assumption: Thursday and Monday are travel days. We assume you will not spend nearly as much due to not being on the island the whole day.

5) Fun in the Sun

How you spend your days will require some tricky accounting and mostly depends on your needs. Here is a fantastic list of activities throughout St. Thomas. Fortunately, we happened to choose a hotel within a mile of many different sites and activities, but if you’re feeling a “I just want to relax by the pool or beach and just do absolutely nothing but burn like a lobster” type of vacation––our favorite activity––it will cost nothing. Regardless, let’s dole out $50/day just in case.

TOTAL COST: $1,069 + $250 (Activities) = $1,319

That leaves you $181 for cool local merchandise, art, or an emergency fund in case that fun night where you fall in love with an ex-patriot local who left the States to chill, relax, and maybe try and steal tourists’ kidneys goes a little sour

Jokes aside, trying to “Caribbean on the Cheap” is actually very realistic if you make certain sacrifices for the trip. And when you get back––hopefully with all human parts intact––you’ll have a true adventure tale to share with all your clients and friends.

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