Few places in the Caribbean are as captivating and inspirational as the elevated deck and winding paths on St. Maarten’s Sentry Hill. The main attraction here is the steepest zipline in the region—possibly the entire world, according to its operators—but you can spend hours, probably even an entire afternoon, wandering from corner to corner and enjoying arguably the most incredible views any island has to offer.
What makes the sights so special here is how clearly you can see St. Maarten’s neighbors. Anguilla, St. Barth, Saba, and St. Eustatius all appear so close that you’ll think you can swim to them, but what I took away from my first time on this hill was the importance of this one particular island. Not just because it serves as a gateway to other islands—its legendary airport on Maho Beach is a crucial hub—but because it is their centerpiece.
Each destination offers something spectacular, sure—St. Barth certainly has its own legacy and reputation that puts in the upper echelon for luxury travelers. But St. Maarten simply does it all, including bounce back stronger than ever from natural disasters and acts of God. Having recently visited and fallen head-over-heels in love with the Dutch side of this unique two-nation island (J’aime aussi le côté Français), it’s time to put the spotlight on the things that make St. Maarten so special and especially the things this island does so well.
We talk so much about beaches, resorts, luxurious amenities, food, views, etc. that we often overlook the glue that binds them all together: the people. St. Maarten is known as “The Friendly Island,” and you won’t be there an hour before you know why. From the moment I sat down for a post-flight lunch at The Captain’s Rib Shack, I could tell this is an island that takes hospitality seriously, and if I didn’t eventually beg them to stop recommending food, someone would have to roll me up Sentry Hill.
Typically, wherever I travel, I believe I’ll meet one person who exemplifies the soul of that island; however, here I met three people. First, there is Ruby Bute. I don’t know if I can do this incredible artist justice with my words but having the opportunity to visit her studio and talk to her about her life, talent, and passions, as well as the inspiration she’s had on St. Maarten’s burgeoning art scene, showed me that there is limitless promise to her home.
The others are Denicio Wyatte and Sunil Vaswani, who both represent different aspects of St. Maarten’s future. The former is the incredibly charming and downright brilliant director of the Spaceless Gardens, a small but plentiful farm that serves not only as a source of fresh ingredients for local chefs, but also education for the community—especially the children—on the importance of sustainable agriculture and how it can make their island better and stronger.
Vaswani, on the other hand, has sacrificed a lot to fulfill his dream of showing St. Maarten’s promise to the rest of the world. In early 2019, he opened the Caribbean Brewing Company in Point Blanche, and in 2021 his Dutch Blonde Ale became the island’s first-ever to win silver at the London Beer Competition, immediately propelling it to the best craft beer in the entire Caribbean. This enthusiastic entrepreneur has since opened the Dutch Blonde Beach Bar, where guests can enjoy the brewery’s five beers and great food with beachside food, and his latest source of pride is the region’s first and only escape room (at which I currently hold the record time).
Next up? A speakeasy with craft cocktails. All because he thinks St. Maarten can and should be the biggest playground in the Caribbean. If anything, it’s destined to be one of the most talked about.
There is A LOT to be said of St. Maarten’s culinary scene, and this will hardly be the only time I write about it. To say that a person could gain a lot of weight here would be an understatement, because I wanted to stop and try every lolo (kind of like a food truck) that I spotted, and I wouldn’t have been able to try half of them if I’d stayed a week.
One lolo that everyone talks about to an almost religious degree is Sexy Beef, which is not, as I initially thought, a butcher shop by day and gentlemen’s club by night. Instead, named after the owner’s affectionate nickname given by her boyfriend, it is the spot where I tried steak, chicken, and pork satays—and also sipped one of the best margaritas I have had anywhere in the Caribbean—and now there are nights when I am staring out the window, thinking about the world, and wondering why I can’t have meat drenched in peanut sauce every day for the rest of my life.
Other lolos lack the name appeal of Sexy Beef but still share the same devotion to simple food done very well. For example, there’s a truck on Longwall Road, across from a car dealership, that serves delicious beef and chicken patties. The name? No clue. I’m not even sure it had one, but I haven’t stopped thinking about my special “Patty Place.”
This isn’t to say there aren’t five-star, high-end, romantic meals to enjoy as well. Book a reservation at Sale e Pepe and prepare to be treated on your first visit like you’re returning for the tenth time. Chef Davide, like a lot of the talented people I met, was lured to St. Maarten for work more than two decades ago, and a combination of success and love convinced him to stay and bring the flavors of Sicily to Simpson Bay. There’s a lot of great Italian food in the Caribbean, but I’ve never seen a menu as extensive as his. It’s truly indicative of this island’s devotion to the “something for everyone” philosophy.
The journey to the top of Sentry Hill begins with an important visit to the Emilio Wilson Museum, where guests will learn about the life of Trace Wilson and her descendant for whom this fascinating property was named. Learning about any island’s history will make you appreciate it so much more, but here it is enhanced by the opportunity to take the Soualiga Sky Explorer to the top—after a quick, thrilling ride on the schooner—and look at this majestic destination with and compared to her surroundings.
This is hardly the only spot for awe-inspiring moments in St. Maarten, though. For example, guests who stay at Divi Little Bay can take a quick hike to Fort Amsterdam to imagine the cannons roaring, and most island tours will stop at Bell’s Lookout Point on Cole Bay Hill to appreciate the views from beneath the flag. Don’t even discount the idea of a long stroll through Philipsburg, checking out the shops and admiring the charm of the old Dutch architecture. (For the most Instagram-friendly shots, pop through the lobby of the Holland House, where the hotel’s stylish design makes the awesome stretch of sand even more stunning.)
Some of the best views also come from the water. Book a catamaran tour with Pyratz Gourmet Sailing and other Caribbean boat rides might be ruined forever. The young French couple that operates this company plays magnificent host to small groups, serving delicious snacks, cocktails, and meals that are made onboard, while showing everyone some of the most beautiful locations around the island. Just try not to get too jealous of any massive yachts anchored near La Samanna on the French side.
But if you want a strong blend of people, serenity, adventure, and natural beauty, book a trail and beach horseback ride with Lucky Stables at Seaside Nature Park. Better yet, make it the two-hour champagne sunset ride and bask in the glory of what residents call the best sunset in the Caribbean, all while learning about St. Maarten from one of the charismatic trainers. (And if you end up riding the mare named Magic, make sure she’s nowhere near Lucky, because those two will just do whatever the heck they want.)
Oh, and the best sight of all? The airplanes landing over Maho Beach. Visitors will obviously want to get down to the sand to experience this legendary setting, but the best way to watch is from a table at the Sunset Beach Bar. Grab a cheeseburger and a marg and have the phones rolling to catch each aircraft as it lands, because it never fails to blow your Instagram followers away.
The hardest part of any trip is deciding where to stay, and on St. Maarten it’s all about preferences. The all-inclusive crowd, particularly fun foodies, will be pleased with Divi Little Bay Beach Resort’s location, first and foremost, but also everything we’ve come to expect from this brand. Grab a Guavaberry Punch from Gizmo’s and find a chair on the beach for spending a morning and/or afternoon with your toes in the sand before a night of seaside karaoke and dancing.
Kids will be in heaven at Sonesta Maho Beach Resort, the island’s largest all-inclusive option, as it boasts the exciting Aqua Park, where little Caribbean travelers can tire themselves out at the Beach House Kids Club and on water slides. Adults can escape to Casino Royale and the Serenity Spa before everyone meets up again for dinner at one of the many excellent dining options.
For longer stays with bigger groups, or anyone seeking extra privacy, a rental house will make guests feel like they practically live there. Jennifer’s Vacation Villas, for example, offers a wide variety of options, from one-bedroom beach apartments to the palatial and extraordinary Les Jardin de Bellevue, which, with up to eight bedrooms, is so big it feels like a resort. For the ultimate family celebration, choose the five-bedroom Caribbean Blue beach villa and then see if you can ever leave the infinity pool. Little challenges like that make for even better vacations.
The story of how St. Maarten and St. Martin came to settle on a border is a fun one, even if some people doubt the authenticity of every detail (hey, you try walking 18 miles with nothing to drink but gin and see how much ground you cover). What it tells us, though, is that not much has changed in more than 350 years—this is still an island that operates on cooperation over competition.
When it was devastated by Hurricanes Irma, Jose, and Maria within a span of two weeks in 2017, the island suffered more than $3 billion in damages and losses. Missteps and mistakes in recovery, as well as finger-pointing and “drama” within the government, led to confusion and despair. Some places would have never recovered, at least not to where they were prior to the storms. But St. Maarten isn’t “some place.” Residents took it upon themselves to help each other, to prepare and deliver food, and round up tools and workers to make crucial repairs to roofs, to make homes livable and reopen stores and businesses again.
In that effort and camaraderie, many people saw an opportunity to raise St. Maarten even higher. Why settle for being a charming island where travelers stop before connecting to St. Barth or Anguilla? Why not be their destination in the first place? Since that unfathomable hurricane season, the resorts are back, more amenity-packed than ever, the tours and excursions are in full swing, and the people have an energy that can only be described as infectious.
Now is the time for people to fall in love with St. Maarten, because tomorrow she’s going to be something far more spectacular than anyone ever imagined.