New Yorkers, You’ll Want to Escape the Cold on a Private Charter to Anguilla

The picturesque Caribbean island isn’t the easiest place to get to, but this new direct flight makes it a breeze

February 28, 2023 6:35 am
aurora anguilla white sand beach and blue water
You could be sitting here in mere hours
Max Schwartz

There are few things better than stepping into a hotel lobby and being handed a glass of rum punch on arrival. I’ve experienced this as the standard greeting at a few different hotels around the Caribbean, and it’s a delightful welcome each and every time. Most recently, I found myself sipping a version made with dark rum, coconut and passionfruit while checking in at Aurora Anguilla Resort & Golf Club, an idyllic resort that just underwent a multimillion-dollar renovation before reopening in Dec 2021. I sipped the sweet, tangy punch and took in the picturesque pool and beach scene that lay beyond the open-air lounge while we checked in. My husband and I had just arrived on a charter flight from White Plains, NY, an Embraer-170 that shuttled us from a private terminal at Westchester County Airport to Clayton J. Lloyd International Airport in Anguilla. 

Anguilla isn’t the easiest Caribbean destination to get to, which probably explains the extra laid-back, not-at-all sceney mood on the island. It usually requires a flight into nearby Saint-Martin and either a tiny plane or boat ride to Anguilla. Those who don’t have a lot of days to spare or are prone to seasickness (like me) might opt for a direct flight to a different destination. Which is why the direct charter flight from Westchester to Anguilla is such a game-changer. 

aurora anguilla private plane
Your chariot awaits
Max Schwartz

First off, not having to deal with the hassles of airport crowds and security gets you into the island mindset before the boarding process even begins. Aurora Anguilla has a fleet of four planes that range from 30 to 64 seats, depending on demand. The legroom on our 30-seater was more than abundant, and cocktails, wine and beer were served in real glassware, a simple touch that feels like a remarkable luxury in contrast with the plastic cups on commercial flights. The meals were decent too — especially a beef tenderloin served with roasted potatoes and veggies on the return flight. 

But back to that rum punch. The tropical beverage went down easy as our personal concierge, Roddy, showed us to our room, an airy, expansive space that opened to a private terrace overlooking the vibrant blue sea. Roddy and I exchanged phone numbers so we could keep in contact with any questions or requests throughout the long weekend. 

Redezvous guest Room at aurora anguilla resort
Just imagine waking up to this view every day
Kris Tamburello

Aurora Anguilla hosts a lobster beach barbecue with live music every Thursday evening. Even though ours got rained out (the only time during the trip that unpredictable tropical weather canceled a plan), the delicious grilled fare was moved to one of the open air restaurants on property. Succulent spiny lobster, coconut snapper, seafood paella, barbecue pork and an abundance of salad and veggies gave us our first taste of the resort’s culinary excellence. Resort dining can be hit or miss — whether the food itself is just okay or the property lacks restaurant variety. Not the case here, where the always delicious food ran the gamut from casual beachfront meals to a classic steakhouse dinner, complete with a world-class wine list.  

Local products are one of the reasons the food at Aurora Anguilla is so good. On Friday morning, we joined hydroponics manager Rohan for a tour of the property’s farm. He guided us through his gardens and hydroponic greenhouses, explaining exactly how his team grows everything from passion fruit to eggplant. The fresh produce showed up at every dining experience — the vegetables served alongside the grilled Anguilla crayfish at Breezes, the lettuce that makes up the perfect lobster salad at oceanfront restaurant Eventide, the microgreens placed with a flourish atop the king crab cakes at D Richard’s. 

rohan showing off a plant in the hydroponic greenhouse at aurora anguilla resort
Rohan shows off his expertise in one of the resort’s two hydroponic greenhouses
Max Schwartz

Even the produce that isn’t grown on site is spectacular. After tasting the dragonfruit at breakfast and being completely blown away by its flavor, I asked Rohan if they grow it on site. They haven’t succeeded yet, but they’re doing a great job of sourcing, regardless. The same goes for the chef’s choice sashimi at Tokyo Bay (the resort’s Japanese concept) and Australian wagyu at D Richard’s. The latter should definitely be enjoyed alongside a bottle of wine, which sommelier Bernel hand-picked for us after a tour of the restaurant’s cellar.

During such a leisurely vacation where I’m basically eating and laying by the pool drinking Miami Vices (which are great here, btw, especially with a dark rum float), I appreciate fitness options. (My husband jokes that resort vacations with me are kind of like rehab, but I beg to differ on account of our rosé lunches and evenings spent with the amazing bartenders chatting and tasting rums.) The gym here is really nice and has a ton of equipment, so you’re never really waiting for machines or fighting for mirror space. But one of my favorite activities was a tennis clinic with Ryan Williams. Seven years ago, Williams made the move from corporate life in Atlanta after falling in love with Anguilla, and now he does what he truly loves — teaching and playing tennis. I’ve taken a few tennis lessons in the past, but I’ve never left with more knowledge than I did after an hour with him. 

Why Vacation on One Caribbean Island When You Can Hop to a Second? 
More volcanoes, more rum tastings, more wakeboarding, more everything

I’ve barely held a golf club (unless you count those rinky dink things at the mini golf course), but it should be mentioned that Aurora Anguilla has both nine-hole and 18-hole courses, which are also the only ones on the island. Judging by the amount of guests sporting golf gear at breakfast, it seems like a lot of people travel to the resort solely to hit the links. If golf is your idea of a fun thing to do, this is a great place to do it. 

My idea of a fun thing to do is going to the spa, so massages were had on this trip. I highly recommend the relaxation massage and saving time for both the healing waters hydrotherapy pool and relaxation room, a light-filled rotunda where you can soak in your treatment on cushy chaise lounges. I’m not sure if it was the fine white sand or those healing waters, but my skin felt softer than ever after 20 minutes in the salt and mineral-filled hydrotherapy pool.

aurora anguilla walk to the beach
Daily walk to the beach
Max Schwartz

It’s easy to lay on Aurora Anguilla’s beach with the occasional dip in the sea, but if you feel like a change of scenery, there are two local spots that are a quick, sandy walk away. Sunshine Shack is a friendly beach bar that serves delicious grilled fare and features live music. In the other direction, Bankie Banx Dune Preserve looks like the coolest treehouse you’ve ever seen and also serves food and drinks. Bankie Banx is actually a reggae singer who’s lovingly known as the “Anguillan Bob Dylan,” so he’s often playing live music with his son Omari and other local musicians.

After one last rum punch during check-out, we made our way to the airport to board the charter flight back home. It’s not often I’m excited for a return trip, but this was an exception and felt like a true extension of the vacation. We had to stop in Puerto Rico to go through customs, which was a complete breeze. After showing our passports to the immigration agents, we were back on the plane and on our way in about 20 minutes. 

Sure, at $3,500, the charter flight to Aurora Anguilla is a splurge. But if you can swing it, it makes for one of the most tranquil and delightful winter escapes from cold, grey New York.


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