7 Tips for Traveling to Cuba

If your interest in visiting Cuba has been piqued since President Obama's 2014 announcement of plans to improve relations between the United States and Cuba, you’re in luck: One of the areas in which swift changes have been made is travel. Several U.S. airlines launched direct flights to a handful of Cuban cities in August 2016, and tickets remain affordable and available. Here’s what you need to know to plan your own trip to Cuba.

1. BOOKING A FLIGHT IS EASIER THAN EVER ... BUT THAT DOESN'T MEAN IT'S EASY.

For the first time in the history of the internet, U.S. travelers can book their flights to Cuba online. While flights still can’t be purchased through Expedia, all of the commercial airlines that offer flights—including American, Delta, JetBlue, and Spirit—allow online booking, and a few aggregator sites do as well, including CheapOair (which offers flights from JFK Airport in New York to Holguín).

But just because you can buy your flights from your laptop while lying in bed doesn’t mean the process is simple. Once you book your ticket, you’ll still need to purchase a travel visa (which you can’t yet do online) and you’ll need to be prepared to prove that you fall into one of the 12 categories of approved travelers published by the U.S. Department of Treasury. While word on the street is that authorities aren’t actually checking records to determine whether educational and “people-to-people” trips conform to DoT rules, you’ll want to be sure to stay within the letter of the law.

If you have questions, ask your airline, but remember: Commercial flights are still relatively new, and many airline agents aren’t yet familiar with specific regulations. When possible, get the name and title of the person with whom you speak for accountability’s sake.

2. GET TO THE AIRPORT NICE AND EARLY.

Many airlines and airports offering direct flights to Cuba locate their Cuba flight check-in operations outside the usual “Departures” area. Give yourself the full three pre-departure hours recommended for international flights, and contact the airline prior to your flight date to ask where you’ll need to check in. Also, bear in mind that curbside check-in and similar amenities often are not available for Cuba-bound flights, even if you hold a special reward or member status with an airline.

3. BRING PLENTY OF CASH.

While several major U.S.-issued debit and credit card companies rushed to announce they were arranging for their cards to be usable in Cuba, they've been slow to make good on their word. In December 2015, one small Florida bank was reported to be the first U.S. bank to forge a relationship with Cuba's central bank, and in June 2016 they debuted the first U.S. credit card to work there. But don't get your hopes up: Very few Cuban vendors have point-of-sale machines that work with U.S. plastic.

With none of the large U.S. banks operating in Cuba, you also can't withdraw cash from Cuban ATMs. Which means you need to bring your funds with you. The catch here is that you will always lose an automatic 10 percent when you exchange U.S. dollars into CUCs (Cuban Convertible Pesos) at a CADECA (the official currency exchange office). Finally, Cuba still has a dual-currency system. There are CUCs, which tourists tend to use, and CUPs (Cuban Pesos), which Cubans tend to use. When being charged for goods or services, be sure to ask what currency is being used. While there has been talk about moving to a one-currency system since 2013, no timeline has been announced and both currencies remain in effect as of this writing.

4. BE PREPARED FOR A DIGITAL DETOX.

In many ways, Cuba—or Havana, at least—is more digitally connected than it has ever been. Wi-Fi service is increasingly ubiquitous in the capital’s parks and public spaces, and prices for Wi-Fi access dropped significantly in December 2016. And with AT&T announcing roaming capabilities in October 2016, it’s possible to stay connected throughout your visit to Cuba. However, service can be pretty pricey, at $3 per minute for voice and $2.05 per MB of data. It may be easier (on your wallet and mind) to just disconnect completely.

5. DON'T PLAN ON WINGING YOUR ACCOMMODATIONS.

I’m a traveler who’s typically happy to forgo trip planning micro-management in favor of serendipity, but when it comes to accommodations in Cuba, this is not a good plan. Upon landing and proceeding to Immigration, you’ll be required to provide the address of your lodgings while in Cuba. Beyond potentially causing problems with entry into the country, you will also be hard-pressed to find accommodations if you don’t know Cuba well and you wait until you land to look for a place to stay.

Airbnb now lists more than 300 options all over the island and is likely the most affordable, accessible, and simple way for Americans to book a place to stay before they touch down.

6. INDULGE IN RUM AND CIGARS TO YOUR HEART'S CONTENT.

Don’t worry about rum and cigar limits! In October 2015, the Obama administration announced that Americans returning from trips to Cuba can pack their bags with as much alcohol and cigars as they can carry (subject to the standard duties and limitations, of course). Be sure your wares are legit, though; plenty of hustlers, including employees at cigar factories, are keen to sell boxes at cut rates, but these boxes aren’t likely to pass muster if inspected. Waited 'til the last minute to do your shopping? You can buy cigars at Duty Free shops in the Havana airport.

7. BRACE YOURSELF FOR CHANGE.

It's important to remember that these policies are still in flux, so stay apprised of changes by regularly checking in with the Department of Treasury’s Office of Foreign Assets Control.