Hidden Gems

Hidden Gems of Anguilla

Imagine a small island in the British West Indies with just 13,000 people, no cruise ships, no big shopping malls and no casinos, but with everything that defines the Caribbean the way it used to be. It’s uncrowded, has clean beaches, a slower pace, and is an opportunity not just to vacation well, but to think and…exhale. Here are some of my hidden gems of Anguilla.


The island is small. It’s manageable, a place to literally unwind. It’s uncrowded and has an abundance of choice: 33 nearly empty white sand beaches. It sounds great, but first you have to get there.


One of the big challenges in Anguilla is airlift. You won’t find the big U.S. airlines here at the airport. In fact, you won’t find many passengers either. American Airlines did fly here, but it pulled out in 2008 after the recession and they never returned. So, how do people get here?


It’s not exactly a nonstop trip. While there are more than 20 airlines that fly into neighboring St Maarten, that’s just the beginning of your journey.


First, you’ll go through immigration and officially enter St Maarten. Then it’s into a van for the short ride to the ferry dock, go through immigration again, and five minutes later, leave St Maarten. Then on to one of the small 40 foot boats.


On the way out of the harbor, you’ll notice dozens and dozens of partially submerged yachts and fishing boats. These vessels sank here in 2017, when Hurricane Irma hit the island as a Category 5 storm, and they’ve been abandoned ever since. It is not the most welcoming image, but a harsh reminder of the fragility of the islands here amidst the beauty.


Soon you’re out into the open sea, and 30 minutes later, the boat pulls into Blowing Point.  You’re now in Anguilla and once again you go through immigration.


Welcome to Anguilla, and that’s where the scenery and the pace changes dramatically, but first some history.


Anguilla is located in the eastern Caribbean Sea, just north of St Maarten and east of Puerto Rico. It was first settled by indigenous people who migrated from South America. It’s believed that Frenchman René Goulaine de Laudonnière may have been the first explorer to reach Anguilla in the 16th century, but it’s also likely that it was colonized by English settlers from Saint Kitts who brought slaves to the island with them.


During its early colonization period, the island was administered by the British through Antigua, but it later became part of a federation with Saint Kitts and Nevis, with the three islands officially becoming an associated state in 1967. Anguilla formally seceded from Saint Kitts and Nevis in 1980, and today, this 35 square mile island is an independent British overseas territory.


Part of the charm of this island is that it’s only 16 miles long, and 3 miles wide – about the same size as Manhattan – but with little traffic, a fraction of the population. And while it sounds like a cliché, it’s true: postcard perfect beaches and lots of them.


It’s been said that if you have the determination to get to Anguilla, you’ll always return. A number of those original visitors won’t go anywhere else, like Geoffrey Fieger. He first came down here with his wife in 1984, and for all intents and purposes, he’s never left.


“The people are incredibly great and I felt good here,” Fieger said. “I can’t describe the feeling.  I just felt good here.”


In Anguilla, he’s more or less a local, but only here. Geoffrey Fieger is actually one of the most well-known trial lawyers in the United States. He’s made millions representing clients in very high-profile public interest cases. He’s also been the legal expert on many of the major cases he hasn’t handled. Fieger still practices law in Michigan, but down here in Anguilla, among other things, he practices driving.


“Anguilla is a tropical paradise,” Fieger said. “It’s in the old fashioned sense of the Caribbean, and it’s one of the last outposts of what people imagine it to be.”


He also knows where to eat. Welcome to globalization. I’ve had great Chinese food in Amman, Jordan, the best Indian food in London, and for Italian, Fieger has been coming to Trattoria Tramonto for as long as he’s been in Anguilla. It’s a place where the view matches the food, and it sits on Shoal Bay West. There’s a secret at the other end of the beach, which has a completely different vibe.


The Madeariman Bar and Restaurant has been around forever, under different names. This part of the beach was one of the first places Fieger came to. You’re likely to find more people here than most other beaches, though it’s still pretty empty by most standards. With all of the accessible reefs, it’s also great for snorkeling.


Surprisingly, some of the real beauty in Anguilla is inland, and Fieger sent me to Katouche, an 80 acre property that contains its own mini-rainforest. Katouche has been in the same family for generations, and owner Josie Gumbs-Connor and naturalist Oliver Hodge took me along for a special look. I soon discovered the rainforest is nothing less than a fully-stocked natural pharmacy.


There was the ram goat bush used to kill the pain of toothaches, the mauby tree which produces soap when you add water and rub your hands together, and the balsam bush which can help with bee stings, but has also been used for nail polish.