Soaking up the Sun in St. Maarten


Last week, I got the chance to travel to the island of St. Maarten with my mom and brother for a long overdue family vacay. St. Maarten is a Dutch Antilles island that’s half Dutch and half French, while still only being about 13 square miles. We spent six days on the island, staying at the Simpson Bay Resort and traveling a bit around the area. Warning: contents ahead may be incredibly relaxing.


We got in around 4pm on Sunday afternoon after a bright and too early flight out of O’Hare… (P.S. If you don’t do TSA Pre-Check, do it. It literally saved us on either end so highly recommend it.) We grabbed a pre-dinner margarita and made our way to Skip Jack’s, a local restaurant owned by a business friend of my mom’s and voted best seafood on the island. We gorged on rich crab dip, fresh tuna carpaccio, and Caribbean lobster, an enormous kind of local lobster with giant spined antennae instead of claws (check the food pic below and please note the fork for scale, that thing is fuckin’ huge).


The next day, we met up with the same group for a little island hopping (we even had to bring our passports along because we were technically entering a different country). We hopped aboard the Nitro, grabbed some gas on the French side of the island, and set off for Anguilla, a British territories island. After peeling the sunglasses off our faces from the speed of the boat, we were treated to a totally deserted beach with soft sand and mango margaritas within 20 feet of our sunbathing. We sunk into a long afternoon of fish & chips, frozen cocktails, and hanging with Joe, our newest (and smallest) beach companion. We definitely got spoiled because the rest of the beaches we went to were rockier and rougher, but like a beach’s a beach, am I right?

Anguilla is home to August Monday, one of the biggest beach parties around. Our friends told stories of the entire bay (pictured below) filled end to end with boats and thousands of people partying on the beach. They said how murky the water became by the end of the day because of well… you can imagine.

I also sustained a brief ankle injury from having an iguana (below) thrown at me and jumping down half a flight of stairs. Don’t hear that excuse every day.


The next couple of days blurred together into a daze of beaches, heinekens (think Dutch), and mixed restaurant reviews. Unfortunately, we weren’t too impressed by the restaurants at our resort, apart from a little French place we went to for breakfast and dessert every night. We also had a small bout of food poisoning from the resort’s Italian restaurant that shall not be named… And while we’re on the topic of places to avoid, do not make a massage appointment at the resort- let’s just say I had a massage that only Troy Barnes would have enjoyed.

But I don’t totally want to shit on Simpson Bay; our room was wonderful, the beach was easy to access, and the sea side bar had a great happy hour deal. I would just recommend renting a car to explore other parts of the island, as well, especially when it comes to dining.


By far my favorite day was our road trip around the island, which we did on our last full day. There is literally one main road around the entirety of St. Maarten so navigating was especially easy and you can get around the whole island in an afternoon. We passed blatant knockoffs of American chains (Seven Alive instead of Seven Eleven, Zoo Rock Cafe instead of Hard Rock, etc.), banks that used to be Pizza Huts, and more coconut retrievers than we could count (island dogs that are so mixed they don’t have a particular breed anymore). St. Martaan is nicknamed the friendly island and watching drivers stop in the middle of traffic just to high five pretty much cemented that for me.

The highlight of the day, though, was the incredible lunch we had at a beach side French restaurant we literally just stumbled upon on the French side. It’s so open and relaxed, I’m not even sure the name of it, but it’s on Palm Beach along Orient Bay. Nothing like sipping white wine with baked Camembert, homemade foie gras, and grilled fish at 1pm to make you feel like you’re on vacation. It was far and away the best meal we had on the trip and I basically reached my limit of rich food at that point. It was pretty much beans and rice from then on…


The island is obviously beautiful and the weather incredible, especially after the shock of a Chicago winter, but in all honesty, the colonial history of the island made me pretty uncomfortable at times. It was hard to ignore the cultural appropriation a lot of tourist spots were selling and that (white) people were totally eating up without a second thought. I wasn’t brave enough to broach the subject with anyone local, but I can’t help but wonder what those who live on the island think of the European occupation of the island after so long (the island was first claimed in 1493 by Columbus).

Of course, I feel hypocritical for pointing this out while being someone who gladly participated in and supported the tourism of the island, but it also becomes so easy to simply look past it and just see beautiful beaches and pina coladas. If nothing else, it has reinforced my desire to have more culturally authentic experiences when I travel. Maybe the internet isn’t the best place for this kind of conversation, but I would love to hear people’s thoughts.


Although we had a great time on the island, the best part of the experience was spending some solid time with my family. Living abroad has made me miss our goofy, fun, sometimes dysfunctional way of being a family and, no matter how far you feel like you’ve come in life, nothing is more humbling than getting slugged in the shoulder by your older brother for absolutely no reason. Till next time!


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