An Island is a Snowflake

How Each Caribbean Island Differs From One Another


By Jackie Leavitt

When I flew into the Dominican Republic in mid-March two months ago, it was the first time I had set foot on any Caribbean island. My perception of this area came from Internet pictures, short stories from friends and families who had vacationed there, and the research I had done for one country: the DR. It was easy to look at a map and make general assumptions — that’s what we do as humans when we don’t know something.

How was I to know that each country and territory — and even smaller islands within the territories — would have such a different culture and feel from one another?

Here’s a one-sentence recap from my experiences of the islands I’ve visited so far during the two months I’ve been traveling through the Caribbean.


The people of the Dominican Republic hustle like bees, buzzing in color on motorcycles, cars and guaguas under lush palm tree–covering mountains that tumble into the sea.

Puerto Rico’s empty sea-side streets with closed restaurants lead to giant, American shopping centers (like Walmart), surrounded by dry, hot bushy hills.

Vieques, the U.S.’s former shelling ground, has eager guests treading lightly by day around the pristine sandy coves with palm trees and possible unexploded artillery, and at night, floating through the bays’ green-glowing bioluminescent algae.

American ex-pats, locals and cruise-ship tourists mix on St. Thomas’ roads, past yacht and seaplane harbors, boating mechanic shops, Walgreens, an empty ‘disco’ and bars with occasional live music and ladies’ night once a week.

Little purple-and-white squid dance in Christmas cove’s waves among the flashy coral fish floating around the rocky coral of the uninhabited Great St. James I.

Eyes large as saucers, St. John’s swimmers glide next to nonchalant sea turtles munching on grassy of the protected bays that curl under rolling mountains, sprinkled with abandoned stone sugar mills.

Only those clever enough to escape the ferry and sailing charter–central of Tortola’s Road Town will discover the locals’ lush beach communities with sandy bars, full-moon mushroom parties and dive-bombing birds hunting for minnows in the turquoise waters.

Jost Van Dyke is an island of tiny beach-lining bars, with one harbor pumping music from Foxy’s (whether people are there or not), and another cove with the laid-back Soggy Bottom Bar, the infamous inventor of The Painkiller drink, which lives up to its name when you’re seeking some hair of the dog after a night of indulgence.

Massive conch — easy to catch and hard to harvest — lounge in the leeward side of Little Jost, a sandy spit of sunny land that kicks up wind for kitesurfing fiends just northeast off of its big brother island.

My kingdom for a cafe with good espresso and fast wifi, our sailors lament — we find it with Cooper Island, inhabited by a eco-resort paradise with the happiest of happy hours and casually chic wooden beach chairs overlooking the sunset-drenched harbor.

Around the corner from Norman Island’s sea caves floats an old steel pirate ship bar, Willy T’s, that serves up a raucous evening and free shots for ladies’ topless dives off the second deck.

In the Dog Islands, divers can explore in wonder and glee around scraggly, underwater, coral-covered rock cliffs and through a sunken airplane, where massive Jack fish linger where travelers use to sit.

It feels like swimming and climbing through a god’s gigantic marble game that spilled out into the sea on the south side of Virgin Gorda, which seems like another world from the island’s northern dry, barren hills, inhabited by sailboats, harbor bars and luxury resorts.

Flat, flat, flat land stretches seamlessly out into reaching coral reefs on all sides of Anegada, home to massive conch and lobster meandering the shallow waters beneath the boards of exuberant kite boarders.

A tiny spec on a map, Saba’s walls of green cliffs climb high into the clouds and down into the deep blue waters, sheltering and preserving the sea life and tiny island community from the easily spoiled outside world.


Puerto Plata, DR

Puerto Plata, DR

Wildfire in Puerto Rico

Wildfire in Puerto Rico

Beach on Vieques

Beach on Vieques

St. John's in the U.S.V.I.s

St. John’s in the U.S.V.I.s

Hidden coves of Virgin Gorda

Hidden coves of Virgin Gorda

The view from Cooper Island's eco-resort.

The view from Cooper Island’s eco-resort.

The view from Soggy Bottom's hammocks on Jost Van Dyke

The view from Soggy Bottom’s hammocks on Jost Van Dyke

Massive sea-side boulders at Virgin Gorda

Massive sea-side boulders at Virgin Gorda

Sailing into Saba

Sailing into Saba

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