Arriving in Anguilla



Our trip to Anguilla from the west coast of the United States involved three flights, including a redeye, and a blurry-eyed combination of layovers and airport food in two separate countries.  The silver lining was that, by the time our third flight rolled around, I was delirious and desperate enough to get on the tiny plane that took us to our final destination.

And it is not just the size of the plane that was disconcerting.  When we arrived in the Saint Martins airport and got off our plane from Philadelphia (why we were routed through there remains a mystery), we were already befuddled.  We were supposed to transfer to a third flight but had no boarding pass and our bags were not checked through to our final destination of Anguilla (the woman who checked us in at the San Francisco airport just gave us a blank stare when we mentioned this final flight from Saint Martins to Anguilla).  I was just getting ready to ask someone when, out of nowhere, a chipper young woman appeared with an “Anguilla Air” shirt and a clipboard.

I approached her hopefully. “Hello. We actually have a flight on Anguilla Air?  Regoli?”

“Oh yes, I was looking for you. I want to get you on an earlier flight.”

“That would be great!  When does it leave?”

“Two pm. Or after.”  She took us to a counter, wrote our names on a piece of paper (yes, a an actual physical piece of paper), took our luggage tags, and gave us boarding passes that included no information whatsoever other than the flight number and departure time. “Just ignore the time,” she advised.  “Go to Gate C4.”

“How will we know if our bags made it onto the earlier flight?” I asked.

“I will be there.  I will tell you.”  And then she disappeared with our luggage tags.

We dutifully trotted off to Gate C4 and waited there hopefully, despite the fact that no flight to Anguilla was mentioned on the marquis there. More disturbingly, no flight to Anguilla was listed anywhere, including on the main departures board. As two o’clock came and went, I started to imagine our luggage disappearing into some Saint Martins black market for sunscreen and crocs.

At 2:13pm, the Anguillan air woman reappeared through Gate C4, cheerfully waving us onto a bus that took us to the smallest plane I have ever seen on a commercial runway.   It had a seat for the pilot, with three bench seats behind him, and that was it.  We were eyeballed and told to sit so that the weight on the plane would be balanced.  At first, I thought the man sitting next to the pilot was a co-pilot. But, it turns out he was just some guy the pilot knew. Up went the doors, up went the plane, and then right back down again on the next island, my nine-year-old clinging to me in delighted terror. We were in Anguilla.


The Anguillan airport architectural style is concrete bunker circa 1960. Not a bench has been updated since. It was perfect. I did not come all the way from California for some Disney version of the Caribbean.  (I did, however, say a little prayer that our hotel did not have same look and feel.)

After a lot of input from the locals outside the airport, it was determined that the transfer to our hotel (which we had already paid for) would take place in a taxi cab, the only one in sight. Our driver regaled us with a twenty-minute history of Anguilla on the way there. Both Mark and Jake feel asleep, but it was good stuff. Here is a summary:

At the end of the colonial era, the British created a territory made up of Saint Kitts, Nevis, and Anguilla. The capital of this territory was Saint Kitts, and all British money was filtered through the government there.  Unfortunately, the people of Saint Kitts did not see any reason to send dime one to Anguilla.  As a result, Anguilla had no money for roads, medical services, electricity, or infrastructure of any sort, a situation that persisted well into the 1960s. The British government was not aware of the situation or did not care or could not find Anguilla on a map. In any event, the Anguillan people figured they needed to take the situation into their own hands, so, in 1967, they expelled all St. Kitts officials from the island. The British, presumably because they did not want to go down in history as having lost a war with Anguilla, sent in paratroopers to figure out what the hell was going on.  They were greeted by a bunch of Aguillans armed with three sticks and the truth and taken on a tour of the island (at stick-point, one supposes).  No one was hurt.  The paratroopers went back to Britain with two reports: (1) the state of the island was indeed shockingly bad and (2) Anguilla had the most beautiful beaches in the world. The crown stepped in and eventually separated Anguilla from Saint Kitts, a few hotel developers stepped in and stepped up, and the rest is history.

I looked at the taxi driver in amazement. “That is a crazy story.”  Mark let out a loud snore, and we pulled up to the completely charming Mallihouhana hotel.

Note:  The taxi driver’s story was a reasonably accurate history of that time period in Anguilla.