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Antwaun Sargent’s Lightly Planned, Restorative Week in Barbados

Boat tours, scenic drives, and seaside drinks with Rihanna.

Photo-Illustration: The Strategist; Photo: Courtesy
Photo-Illustration: The Strategist; Photo: Courtesy

Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations/itineraries possible. In this recurring series, we find those people who’ve done all the work for you and have them walk us through a particularly wonderful, especially well-thought-out vacation they took that you can actually steal.

Art critic Antwaun Sargent travels a lot, but almost never for pleasure. “I’m pretty frequently in places people go to vacation, like Italy, but I’m usually working.” But during the last weeks of the year, around Christmas and New Year’s, he gets a rare break. “The art world sort of shuts down, no one’s on email. And honestly, no one cares where I am.” In 2019, he took the opportunity to travel with his friend Miles Greenberg to Barbados, where his family owns a house. “I found a place where people just hang out. I took extremely long walks on the beach, swam, and just cleared my mind. It ended up giving me the moment I needed to take in and process the year.” Last year, he went back, this time with several famous friends in tow, including Jeremy O. Harris and JiaJia Fei. Here, Sargent shares what he’s learned about the island, including why you should rent your own house, what kind of curry to order, and where you might run into Rihanna.

Day 1

1:30 p.m.: Arrive in the early afternoon 

There aren’t a ton of flights to and from Barbados. But if you’re in NYC, JetBlue does an easy one from JFK that’s about four and a half hours. It’s pretty comfortable. Once you arrive, the airport itself is tiny, so it’s really easy to find your way around and out. But you will notice that you can easily get outgoing flights to any other Caribbean island, Canada, and a lot of different parts of Europe. One year, after we had spent Christmas in Barbados, we all went to Reykjavik, where New Year’s is a really big deal. If you’re looking to have a hot Christmas and a cold New Year’s, there’s really no better way you can do it.

3 p.m.: Rent a beach house on the Caribbean side 

The main reason I’ve started going to Barbados is because my friend’s family has had a house there for a long time. He’s spent a lot of summers and holidays there. The house is on the water next to Gibbes Beach, which is my main tip: Stay on the water. If you’re there to surf, stay on the East Side, next to the ocean. But if you want those waters to be calm and chill, like I do, stay on the Caribbean Sea side, the West of the island. It should be pretty easy to rent a house on either side, through something like Vrbo or a luxury service like Altman Real Estate, throughout the year that is basically on the beach. If you would prefer to stay at a hotel, there are great ones there. The biggest luxury one is Sandy Lane (Sandy Lane St. James, BB24024, Barbados), where Tiger Woods got married. I’ve heard it’s nice, but you have an equally good experience if you just stay at a beach house. Plus, all the houses have a house staff and someone who is managing the property. They’ll cook for you, clean for you, give you recommendations for things to do, and connect you with people who can help you do them.

4 p.m.: Coordinate your transportation 

In my experience, most of those houses also come with a driver. Which is great; Barbados isn’t a big place, but it can be tough to get around without a car. There is a bus system, which I’ve taken into downtown, but it doesn’t run that frequently. The driver on staff at Miles’s house was able to take us everywhere we wanted to go during the trip. If you can’t hire someone through your house, Airbnb, or hotel, you should be able to get one either through the staff of your house or through one of the many car services available on the island, like Terrvette Tours, Five Star Fast Track, and Ambitious Tours and Taxi.

5 p.m.: Pick up wine and fancy vinegars for the house

I’m not a big vacation shopper; I’m just super-meticulous about what I require and buy. One thing that’s nice is that the dollar is like, two to one, so the island isn’t that expensive. Everything is really fucking cheap. So we did buy a lot of provisions at this organic food shop called Gourmet Shop (#5 Chattel Village, Highway 1). It’s the place on the island to buy nicer wines, cheeses, special vinegars. It’s like a foodaholic’s dream. That’s where we’d get any of the expensive shit you want that you might be used to in New York, if you’re craving something specific.

Day 2

10 a.m.: Head to the beach 

Barbados is one of those places where the main activity is just going to the beach. And because all the beaches in Barbados are public beaches, all the beaches are good. It’s not like the best beaches are private, where you’d need something special to get in. I like that because it means that, no matter where you’re staying, you’re not cut off from anything, you’re not cut off from the culture. I spent the most time at Gibbes Beach myself, since it’s next to Miles’s house. But I also like Mullins Beach and Brandons Beach. You can’t really go wrong. There’s nowhere on the island you can’t be. And there aren’t a ton of rules on the beach once you get there. Everyone is BBQing, drinking, in the water, all sorts of things.

We spent a lot of time just hanging out in the house and on the beach. We played some games, some people read books. But I really like to completely unplug and hang out. I took a lot of extremely long walks, like for hours. As an end-of-year vacation, that lets you take in the year and reflect on what went well, what didn’t, and really process everything, Barbados is a perfect place.

1 p.m.: See the island by car

There’s a lot of touristy stuff on the island, like the downtown and this plantation on the island, but I’m not really big into attractions. What I love to do is take these long drives around the island, mostly from the West where we were staying to the East. It would take you about three hours to do a full loop, but our drives were more in the hour to two-hour range. The island is so beautiful, and the scenery changes so dramatically as you drive from the sea side to the ocean side. You see these incredible landscapes as you drive around the island, without there necessarily being specific places where you need to stop.

3 p.m.: Take photos at the Animal Flower Cave

This is the one “touristy” thing I would suggest. The Animal Flower Caves (North Point, Conneltown) are on the northern tip of the island. It’s this rocky area with a cove. You walk into it and around and you get these super-picturesque views of beautiful water through these dramatic, large rocks. The rocks kind of form into these windows that you can look through. You just get to see the beauty and power of the ocean. Sometimes you can see humpback whales. There’s also some really nice hiking and a decent restaurant.

7 p.m.: Try the curry … everywhere 

My favorite thing to eat in Barbados is curry. Because the island is part of the West Indies and was a British colony until 1961, there is curry all over the island. It’s a product of that cultural exchange between colonies. And it tastes amazing. I could literally eat curry on the island; I subsist on it. I’m the kind of person who can eat the same thing over and over again, and on this vacation, I got curry everywhere. I like the one at Chutney’s (The Walk, Welches, St. Thomas), which is a chain with several locations on the island, but I mostly ate the curry made by the house staff.

Day 3

11 a.m.: Spend the day out on the water 

This year, on Christmas Day, we rented a boat and drove out into the water. Barbados famously has like one climate, it’s always like 80, 85 degrees. It’s really great, especially out on the water. What’s so nice about the island is that it’s so small, everyone knows everybody else. If you’re staying at a hotel, you can ask the staff of the hotel for a recommendation. If you’re staying at a house, you can ask the person who manages the property. If you don’t have access to either, you can book everything from small sailboats (from $90) to massive catamarans (from $767) from services like Set Sail Barbados and Silver Moon. Usually whatever boat you’ll rent will also come with a crew, too. So you don’t have to worry about driving. We took our boat out and did a tour of the island, since Jeremy and his boyfriend had never been before. We had food on the boat, then swam and saw some turtles, fish. If you want to, you can find fishing boats where you actually catch fish, and then bring it back to have it prepared for you at your house.

Day 4

6 p.m.: Try the flying fish at Round House

Barbados is known for its flying fish, a fish I did not know existed before I started going there on holiday. It does what it sounds like; they hop out of the water and float in the air a bit. It’s usually fried in a batter, kind of like cod. But Barbados is part of the West Indies, so the batter is spiced and has a lot of flavor. It offers just a little bit more than your typical New England fish. One of my favorite places to eat it is Round House (Highway Z Bathsheba), which we usually go to after the end of one of these beautiful drives, since it’s a hotel on the ocean side of the island.

8 p.m.: Binge Emily in Paris 

We spent most of our evenings just hanging out together at the house; it wasn’t the kind of vacation where we were going out and partying or anything. Jeremy and his boyfriend are both in the entertainment industry, so we watched a lot of movies. One night we watched the second season of Emily in Paris, because Jeremy is actually in it. It was just a really fun good friend hang. It was totally relaxed.

Day 5

6 p.m.: Grab a farewell beer, look out for Rihanna 

Jeremy and Rihanna are friends, and she happened to be in Barbados with her family. So we all got a drink one night at the Sea Shed (Mullins Beach, Bridgetown), a bar near Mullins Beach. The beer that Barbados is really known for is Banks Beer, if you’re a beer drinker. If you’re not, I would try any sort of rum drink, like a rum punch. The oldest rum, Mount Gay Rum, is made in Barbados.

Antwaun’s Barbados Packing List

A game-night game

Monopoly Deal Card Game

It’s a faster version of Monopoly that you play without a board. We played for hours.

Hot sauce

Aunt May’s is an Asian pepper sauce that goes really well in curry. You can get it anywhere now, I’m sure even on Instacart in Brooklyn, but I’m the sort of person where, if I have something on vacation in a place, I like to leave it there.


Barbados is the kind of place where your main activity is the beach. You gotta use sunscreen to protect your skin.

[Editor’s note: You must create an account on and undergo a skin analysis in a Biologique Recherche center before you can purchase this product.]

A protective hat

Another way to keep your head protected: these hats from designer Rodney Patterson.

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The COVID-19 situation there: If you are traveling to Barbados, you must bring proof of a negative COVID test taken within one calendar day of your travel, even if you are vaccinated. The CDC has issued a Level 4 warning for Barbados, saying that you shouldn’t travel there, but it is possible to do so without taking on an undue amount of risk. As long as you limit most of your contact with others to outdoor activities, ideally with masks, you should be able to remain safe.
Antwaun Sargent’s Restorative Week in Barbados