BLOWING POINT, Anguilla – I normally don’t get the pleasure of a rum tasting at passport control, but on a humid Saturday morning last month, Gloria Leveret and her daughter Julianne were lightly pouring rum into small plastic cups outside while passports were being checked inside.
Leveret, famous (in Anguilla at least) for her company Glo’s Flavoured Rums, came to meet me at passport control when I was unable to get to her during my last morning in Anguilla. She had no idea I was a travel writer, she was just being incredibly accommodating to a tourist who wanted to bring home a boozy souvenir. After tasting more flavors of rum than anyone should taste at 10:30 a.m., I purchased a bottle of pineapple-infused rum and stuffed it in my suitcase before the ferry arrived to take me to the airport in St. Martin.
It seemed appropriate that this would be how I’d say goodbye to Anguilla. It wasn’t just Leveret and her rum that were accommodating. Anguilla, with its beaches, beach bars, and some of the best chicken I’ve ever consumed, charmed the shorts off me.
“It’s such a unique place,” said Sara Steele-Rogers, a former Bostonian who now owns a barre studio called Retreat AXA in Anguilla with her husband, J.W. Craig. “You ask someone for directions, and instead of explaining, they’ll go out of their way and have you follow them there.”
But before we go any further, I think it’s important to get one vexing detail out of the way: How do you pronounce Anguilla? I heard a few different versions before I arrived, but was taught to say it as ann-gwill-ah. In Caribbean island hierarchy, it’s not as glitzy as nearby St. Bart’s, it’s smaller and less populated than St. Martin, and it’s much less commercial than other British outposts, such as the Cayman Islands and Turks and Caicos.
“This is the authentic Caribbean,” my taxi driver said as he drove me to my hotel.
I suspected the “authentic Caribbean” line was local tourism bureau malarkey. If I had a nickel for every time I’d heard of a place being “authentic” I’d have enough nickels to buy my own island and fill it with cats. But the more I learned about Anguilla, the more I learned that the cab driver was not simply spitting out advertising slogans. After a few days, my cynicism, which is the cornerstone of my personality, started eroding. There are no fast food chains on the island. Also, no high rises, no cruise ships, and no casinos.
Most people who come here take a flight to St. Martin (JetBlue offers nonstop flights to St. Martin from Boston every Saturday), and then a ferry from St. Martin to Anguilla. There are very few — two to be exact — direct flights from the United States to Anguilla, so people who want to come to Anguilla generally work to get here. COVID-19 protocols (as of this writing) require travelers to upload a copy of their vaccination card to the country’s website and fill out an application to visit. A nasal swab test must be taken within 48 hours of arrival. Once approved, you are given another nasal swab test when you arrive. The cost of that test is $50.
Anguilla may be sleepier than other Caribbean islands, but you can still find activities such as ATV riding on one of the tiny islands (which are more like oversize sandbars) just off the coast, horseback riding on the beach, or hiking to several highly Instagramable locations. There’s a classic West Indian sloop that will take you out for a day of snorkeling or for a sunset cruise. Boat racing is the national sport of Anguilla, so getting on the water is an essential part of the journey. My snorkeling time was cut short by a choppy sea (as evidenced by the amount of salt water I ingested), but on the days that I was able to snorkel, I swam out, not far from the shore, and encountered some friendly turtles.
What Anguilla lacks in tourist traps it makes up for in white sand beaches (there are more than 30 of them), and hospitality. There’s the kind of hospitality that you can find at the island’s handful of luxury resorts, most of which cater to American tourists. On the high end of the scale is the Four Seasons on Mead’s Bay Beach. Rooms start at $750 a night and go up from there, however 80 percent of rooms come with an ocean view. There are multiple pools on the property, tennis courts, and a beach where you can flop down and idle in the sun. Those staying in villas have access to butlers (!). Even if you don’t have the cash to stay at the Four Seasons, you can still stop in, eat at one of the resort’s four restaurants, and live like the other half does, even if it’s just for a drink and a slice of carrot cake. If you do swing by, let me recommend the Sunset Lounge. It delivers on the sunsets, and the bartenders make a killer rum punch.
There are also an abundant number of mid-range and inexpensive properties, such as Serenity Cottages, Carimar Beach Club, Turtle’s Nest Beach Resort, and the Anguilla Great House Beach Resort. Places that are on (or near) the beach that don’t break the bank.
On the other end of the hospitality spectrum is a gentleman named Sydney Gumbs. The Anguilla native rents out rooms in his home through AirBnb for $150 a night, and he’s also something of an island historian. His breezy multi-level house, filled with family heirlooms and two cats, both named Angus, isn’t on the beach, but on a hill with views of St. Martin and St. Bart’s.
Gumbs invited me to tea, which I assumed meant a cup of tea and maybe a cookie. Instead, he filled a table with enough finger foods for a small wedding party. When I told him I could stay for around an hour he looked at me skeptically and said that we we would need about an hour and a half to talk about Anguilla, so I settled in with a cup of tea and a plate of meatballs. Here are some important things I learned: There are very few secrets on the island. Most residents know what everyone is up to, for better or worse. The island didn’t have electricity until the late 1960s and early 1970s. Before tourism, the main industry was salt. There was a revolution in Anguilla in 1967 to secede from St. Kitts and establish a direct relationship with England.
But for me, the most interesting part of afternoon tea was getting his take on why Anguilla was different from other Caribbean islands.
“I think we are still a bit more unique than the other islands,” he said. “We have great manners, respect, we’re open to people, and welcoming. Those are the things that are important. We still have those values.”
Steele-Rogers and Craig, the former Bostonians who now own the exercise studio in Anguilla, were kind enough to play tour guides and took me around the island. We saw everything from the Anguilla Arch, a natural limestone rock formation, to Nat’s, a roadside restaurant that resembles an orange clubhouse. I had a lot of johnnycakes while on Anguilla (don’t judge), but my favorites came from Nat’s. One of the most important lessons Steele-Rogers and Craig taught me is that some of the best food on the island can be had at nondescript places, such as the Indian food in a blink-and-you’ll-miss-it strip of tiny restaurant stalls, or drinks from the gentleman who sits on a bench and sells pouches of slushy cocktails out of a cooler in the Village.
We tried restaurants such as the Straw Hat, Olas Tacos, and the legendary Sharky’s Restaurant. All recommended. But my favorite options were the beach clubs. At Blanchards Beach Shackyou can dine, drink, and rent a beach chair and umbrella for $5 for the day. I was most smitten with the SunShine Shack on Rendezvous Bay. It really is a collection of shacks, plus a few tables, and a tidy parade of lounge chairs. I swam, I ate the best chicken I’d ever tasted, I drank rum punch, and got sunburnt. In other words, it was an authentic Caribbean day.