Planning Your Vacation to Cuba

Ninety miles south of Key West sits the largest island in the Caribbean, and for most of a lifetime it was the one American travelers could see on a map but not set foot on. That gap between looking and going is a big part of what makes Cuba feel the way it does. It is close enough to reach in an afternoon and just far enough out of reach to have kept its own pace. Here is how to plan the trip, and what the island looks like once you trace it out on a chart.

The shape of the island

Cubans call their island El Caiman, the alligator, and from the air the nickname makes sense: a long, low body of land stretched out across the water, roughly 43,000 square miles of it. Run your finger along a wood chart of Cuba and you get the whole animal at once, more than 3,500 miles of shoreline folding in and out, the main island trailed by a scatter of smaller keys. It sits at the meeting point of three bodies of water, with the Caribbean Sea to the south, the Gulf of Mexico to the west, and the North Atlantic to the north. The topography is mostly rolling to flat, the climate tropical and steady, which means there is no wrong month to go.

The history is still standing

Part of Cuba's appeal is how little of it has been paved over. Modern consumerism mostly passed the island by, so Havana still runs on cobblestones and 1950s American cars kept alive by sheer stubbornness and improvised parts. Walking Old Havana feels less like visiting a preserved district and more like arriving a few decades late.

The island has exported plenty of talent over the years, from Desi Arnaz to Gloria and Emilio Estefan to Andy Garcia. It also adopted a few outsiders. Ernest Hemingway kept a home called Finca Vigia on an estate just outside Havana for twenty years, and it was there that he wrote The Old Man and the Sea and For Whom the Bell Tolls, breaking for drinks with locals at the Floridita bar in town. If you want the shorthand version of Cuba, it is cigars, rum pressed from cane sugar, classic cars, and a literary ghost or two.

Where to stay

Most first-time visitors base themselves in Havana, and Old Havana in particular. On a chart you will find the old city wrapped around the Bay of Havana, its narrow lanes packed tight against the water. That density is the point. Casas particulares, the family-run guesthouses that make up much of the island's lodging, put you inside the neighborhoods rather than beside them, and their hand-built Spanish decor tends to be half the memory people bring home. Trinidad on the south coast is worth a night or two of its own, a smaller colonial town that has barely changed since the sugar trade paid for it.

What to do

Cuba splits neatly into two vacations, and the good news is you do not have to choose. On the water there is snorkeling, diving, deep-sea fishing, and, for a certain kind of traveler, skydiving over the coastline. On land there are centuries of architecture to work through, most of it built between the seventeenth and nineteenth centuries when sugar money was flowing. Trinidad is the best single stop for it, with Plaza Mayor at its heart, the Palacio Cantero that houses the Museo Municipal, and the Iglesia Parroquial de la Santisima Trinidad watching over the square.

If you would rather get out of town entirely, Cuba is a serious birdwatching destination. Something like 368 species pass through or live on the island, and 25 of them exist nowhere else. Among them is the bee hummingbird, the smallest bird on earth at roughly two inches long, so keep your eyes open and your expectations low to the ground. And no visit is really complete without a Cuban cigar, whether you smoke it or just hold it for the photograph. The estimate runs to about 100 separate steps to roll a single one, which is either a fun fact or a decent argument for the price, depending on your mood.

Where to eat

Cuban food carried a rough reputation for years, a hangover from the Special Period when rationing left restaurants working with whatever they could get. That era is over, and the private restaurants known as paladares have turned the food scene into one of the better reasons to visit. The cooking leans on Spanish and African roots with a quiet French accent, built around rice, beans, plantains, and seafood pulled in that morning. Plan your days around the meals rather than the other way around. A quick look at your chart before you set out makes it easier to string together the neighborhoods, and the restaurants worth crossing town for, without doubling back.

Bring the island home

A place you waited most of your life to see deserves better than a fridge magnet. We spent years studying Cuba and its waters on a chart long before the island opened up, and there is a real satisfaction in hanging the finished thing on the wall: every bay, key, and depth contour along that 3,500-mile coastline etched into Baltic birch, the alligator laid out at true scale. It reads as decor and remembers as a souvenir.

Start with the Cuba wood chart, then wander the rest of the Caribbean and Bahamas charts to find the waters next door. If you are still deciding where the trip goes, the best-selling charts are a good place to start dreaming.