Why on Earth would you take two kids younger than 3 to a remote island in the middle of a global pandemic? I asked myself this question many times last month as I embarked on my first attempt to get to St. Martin, my transit point to Anguilla, a Leeward Island in the eastern Caribbean Sea.

I was lured to travel here by the aquamarine sea, 33 public beaches, 80-degree temperatures, amazing hotels and food. And like everyone else, particularly any parent you know, we were desperate to get out of the house with our kids to someplace warm where they could be outside and in the water.

But we could have picked any warm-weather spot in North America or the Caribbean for that. We chose Anguilla for the prospect of a Covid-free destination.

There has been no community transmission of tCovid-19 on Anguilla since March, according to the tourism board, and the CDC puts the British overseas territory in the elite Level 1 category – its lowest risk tier.

In addition to the safety dimension, there’s another allure: travelers coming back to New York from Anguilla are not required to quarantine because the destination has managed the pandemic so well by remaining closed until November and implementing strict entry protocols.

Even in the best of times, Anguilla is hard to get to – either two flights from New York or a flight and a boat – making it an upmarket, but not stuffy, destination. I had visited Anguilla in 2018, right after Hurricane Irma devastated the island. While I was keen to see how a tiny island was once again managing a return to tourism, its CDC Level 1 status was definitely the No. 1 reason we chose Anguilla.

There, we could enter a “vacation bubble” – designed so that hotels and resorts can offer guests access to a variety of amenities and activities within a restricted area. (Visitors aren’t cleared to freely roam the island until passing a negative PCR test on day 14 of their stay, or day 10 if they are coming from a lower-risk country.)

A complicated arrival

Our trip got off to an inauspicious start, to say the least.

The family trek that began at 5 a.m. on a Friday at the end of December ended in us missing our flight, then spending six more hours in two airports in a desperate attempt to rebook.

Was this the best risk calculation? Maybe not. But after having packed and prepared to go on the road with a baby and a toddler, my husband and I went into our persevere-at-all-costs travel mode.

Following that debacle, my entire family, including my preschool-age daughter and nine-and-half-month-old son, went on standby to get retested since our initial Covid-19 test results for admission to Anguilla were due to expire that day.

This is Anguilla’s first line of defense against the pandemic: requiring travelers to wait at least 72 hours after a negative test before traveling there. This policy – mandating a gap between the test result and travel date – is the equivalent of building a moat in front of the castle walls.

I came to terms that we weren’t getting on a plane that Friday and we all went home – momentarily. A few hours later, I dragged everyone to Rapid Test Center on the Upper West Side, where they charge $250 for rapid PCR tests.

The multiple airports and Covid tests in New York weren’t the full extent of our odyssey, since there are currently no direct commercial flights to Anguilla’s tiny airstrip (private jets, however, are plentiful and convenient for those who can afford that route).

So after we were cleared to leave two days later, my family took the conventional method of entry to Anguilla: a four-hour flight from New York to Saint Martin (Sint Maarten in Dutch), followed by a luggage transfer, short trip by van, immigration check, private boat ride to Anguilla, a second Covid test upon arrival, and then another round of luggage transfer, immigration and a van ride to the resort. (Don’t accuse me of promising the journey to Anguilla is easy – even without little kids and a pandemic.)

There was a significant financial investment at stake as well: Anguilla opened its borders in November but with an asterisk. In their own words: “Anguilla is open to pre-approved visitors.” So I applied, paid the required fees – $1,350 for my family – to cover our testing on the island (not including testing prior to arrival), provided proof of insurance and read up on the experience of entering a Covid-free fortress as a tourist.

Inside a luxurious Caribbean Covid fortress

I knew there was a vacation bubble, and we had to stay at our hotel until we received the results of our arrival PCR tests. Still, I didn’t completely understand how that tracked with the promise I made to my almost 3-year-old that we were going through all this hassle so she could swim in a pool the MINUTE we arrived.

After a scenic, open-air, ocean spray-and-rain-speckled 30-minute ride on the ferry (think small boat with an outboard motor that seats a dozen people max) across Simpsons Bay Lagoon in Saint Martin and Anguilla Channel, we arrived at Anguilla’s sole passenger port, the Blowing Point Ferry Terminal.

We were administered our arrival PCR test in an open-air facility nestled between the dock and the border control post, had our passports checked and then we bundled into a private chartered van.

At long last, we arrived at Belmond Cap Juluca, one of the crown jewels of the Caribbean set on the idyllic Maundays Bay. The jaw-dropping beauty of the place instantly made the ordeal worthwhile.

But there would be no dip in the main pool until we cleared our arrival test. I found it difficult to explain to my daughter that Anguilla has caught a handful of cases through this two-stage testing protocol so no big pool until tomorrow.

By the next morning, though, when we found that our Covid tests came back negative, it started to feel like a normal vacation. The sand was soft, Maundays Beach was postcard-picture perfect and we’d all (almost) forgotten all the swabs, planes and boats it took to get there.

Cap Juluca is part of Anguilla’s vacation bubble – a consortium of restaurants and hotels, including the Four Seasons, Malliouhana, Zemi Beach House and CuisinArt, to which tourists are limited for the duration of any trip under two weeks, as well as the taxis that can be hired to whisk visitors between bubble sites.

This includes restrictions on walking down a beach from a hotel property or exiting its gates on foot or bicycle while you are still in the vacation bubble. (Those staying more than 10 days have the potential to test out of the vacation bubble and take off the red bracelet that flags quarantined visitors and residents. In December, two visitors were fined $5,000 for going outside of the tourist bubble during their quarantine period.)

Within the bubble, my daughter made a friend and it almost made me cry tears of joy that they could play in the sand and ocean without masks.

A quieter peak season

Unlike St. Barths, which was almost completely sold out during festive season in December, according to their tourism board, Anguilla is a little less on the radar, or just a very well-kept secret for those who study the CDC list of low-risk Covid destinations.

“The testing protocols were not palatable to our traditional festive guests,” corroborated Haydn Hughes, Anguilla’s minister for tourism. (“Festive” is the industry term for the peak demand period of year-end holiday travel.) “They have been visiting the island for many years and like the ability to dine around and enjoy Anguilla. They have given this year a pass, but we could not compromise the health of our citizens, so we had to enact strict protocols even at the risk of possible poor arrival numbers,” he added.

But that’s the price of going to a destination that has such little community spread of the coronavirus that there is no mask mandate for residents, a rare case where it’s actually not needed.

Still, there were signs that high season had arrived and the island has its game face on. Private planes were jetting in. Over the last weekend of December, Belmond Cap Juluca saw occupancy levels of over 70%. The outdoor Sunset Lounge at the Four Seasons Resort was still a lively – but socially distanced – scene. Tables for New Year’s Eve were going for between $5,000 and $15,000.

Celeste, the restaurant at the glamorous Malliouhana, has a new, young talented chef, Angelica Ampil, who is upping the ante on the already strong culinary scene on the island.

There is no escaping the pandemic, but Anguilla’s measures gave me some peace of mind, a headspace that is increasingly hard to find these days. And that sometimes comes at a hefty price tag that certainly does not make Anguilla a great travel equalizer.

Life on Anguilla does not feel like a normal freewheeling tourist experience. There are some absurdities like having to pay $25 for a taxi ride to go half a mile because movement is so restricted. And spas might not open until the second quarter of 2021.

Baby steps toward getting back to normal

But the vacation bubble is, ultimately, reassuring for Anguilla residents and visitors.

Naturally, some in the hospitality industry, which was at a total standstill for nine months and accounts for 95% of the island’s economy, say the government’s measures go a bit too far.

“I think the quarantine period could be shortened,” said a restaurant worker at an establishment in the vacation bubble that is usually bustling during the holiday season but was half full that last week of December.

Hughes said there has been “tremendous pressure” to relax Anguilla’s rules, but the government refused. “We observed the escalating cases of Covid across the world, particularly in our main markets,” he said.

Like other small islands with limited accessibility, the economic impact of the global pandemic is palpable on the island. “People are going hungry. The situation is dire for many families,” an employee at one Anguilla’s top luxury hotels confided.

Still, the prevailing sentiment on the island seems to be that while its denizens desperately need tourism dollars to funnel into the economy, they are not willing to sacrifice the health of their friends and family since the healthcare system on Anguilla is already fragile.

“The key goal of Anguilla’s approach is to make residents feel safe,” said Tiago Moraes Sarmento, the general manager of Belmond Cap Juluca and a member of Anguilla’s tourism board. “We wanted to start with baby steps,” he said. “Ultimately, we want Anguilla to be the safest destination in the world.”

Top image courtesy Belmond Cap Juluca