Sometimes when I go to certain destinations, I try to read a book that is set in the same locale. While on Malta, I read a trashy romance novel with characters who were rather dreadful and annoying. Yet, when my loan period ran out, I found myself waiting a few weeks to get it back just so I could find out what happened to their predictable lives. Whilst on our way to St Barths, I found myself caught up in the fictitious lives of some elitist snobs who go to St Barths TWICE a year, but also to Nantucket when they see fit. These rich bastards keep popping in and out of the Eden Rock Hotel just for a “light snack” or a drink like ALL THE TIME. It is a real place at a beach off the departure end of the St Barths airport. For context, its cheapest pool bar menu has Aperol spritzes for €30, chips and guacamole for €27, or a club sandwich for €45 . . .you know just a casual afternoon snack and aperitif.

The main character, Olivia, is giddy about getting proposed to by her rich and incredibly boring boyfriend Finn, who is about to make partner at his Manhattan law firm. Ooh! Ahh! I think the author wants me to be impressed by all this, but I find all of these people to be absolutely dreadful. There is a point to me telling you all this. During this offseason, Eden Rock and other similarly priced 5-star hotels are effectively vacant. These polo-wearing, tennis-playing, law firm loving wasps were not to be found. Finn, Felix, Sebastian, Hadley, or Olivia are miles away from these islands, busy terrorizing some other populace.

If you’ve read my previous posts about the Caribbean region, I have not been overly enthusiastic and I believe I know why. In my previous reflections post after going to Anguilla and St Martin, I complained of going to a place that is too easy to get to for most Americans and therefore appeals to a wide range of travelers — some might even use the phrase basic travelers. At the risk of sounding as elitist as Sebastian in my book, you don’t want to be one of a million people doing the same thing. It isn’t about money or looking down on people who book extended stay hotels on St Martin, we were also trying to get away from the pretentious types that have been known to grace the shores of these otherwise idyllic islands. Sometimes it’s nice to be off on your own. And on this trip, we were most definitely alone.

On a place like Ofu island in American Samoa, you expect to be isolated. There was just one place to stay and only six rooms. A small plane landed there once every few days. The Caribbean is a much different animal. From Miami alone, there are 45+ flights to destinations in the Caribbean on any given day. Hotel rooms and resorts are numerous. Cruise ships come with regularity . . .until they don’t. Between late August and November, it all kind of dries up. There is good reason for this. Kids are back in school. Weather is generally not yet painfully cold in the northeast or Midwest, but the weather in the Caribbean is very iffy. It is hurricane season. People’s vacations could be ruined by tropical storms, and bookings are close to nil. Most restaurants and shops are shuttered for months at a time.

So for the vast majority of the population, going to the Caribbean at this time of year is a bit risky. But for those who have some flexibility like famed celebrity couple, Bricole, it can be most rewarding. You may recall that we did have a few issues with flights, but a side trip to sunny and dry Bonaire actually helped us dodge the remnants of a storm passing by the British Virgin Islands.

As everyone’s favorite celebrity couple, we don’t like to be seen by the masses. After all, the paparazzi have long pursued famed couples across St Barths for years. J. Lo and Ben Affleck (Bennifer if you will) were caught having a dispute over high-end jewelry in the town of Gustavia. Harry Styles and Taylor Swift (Haylor of course) had a public breakup on Virgin Gorda. We, Bricole, didn’t need that kind of scrutiny. We had no reason to worry. Beaches were empty. High-end restaurants closed. And despite my best efforts to have a disagreement over expensive jewelry with Nicole, all the stores were closed too.

So if one were looking to do a lot of high-end shopping and fine dining, traveling this time of year would be a bit of a bust. But if you’re looking to get away from the exact same kind of snooty people that are into fine dining and high-end shopping, then you’re in luck. There is of course another downside to all this. With fewer people around for nourishment, the insects had a bit of a feeding frenzy on our bodies. This is not to be overlooked. For anyone who has not had the pleasure of being attacked by sandflies, their bites are about 10x worse than mosquitoes. For one, you feel it when it’s happening. Secondly, the itch is more tenacious and doesn’t go away for about two weeks. This makes relaxing outside on a beach a bit more challenging.

Overall, however, the bug bites were worth it. I never imagined that the Caribbean could be as calm and chill as our impromptu voyage to Bonaire, St Martin, Virgin Gorda, and St Barths. Between unimpeded vistas of the tropical beaches on Virgin Gorda to virtual “private jet” experiences on Tradewind Aviation to St Barths, this was one for the books. We were doing rich people cosplay — imposters on islands that cater to much more affluent travelers, but dropped their prices this time of year for wackos like us. Would I recommend what we did to others? Sure, but it’s a bit risky. We dodged a couple storms, happened to time our flights just right, and made a few adjustments on the way. In a matter of a few months, these islands will once again be inundated with travelers, but for this brief little respite in the middle of hurricane season, they were indeed a tropical paradise. You just have to be okay with small planes and small bugs.


