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Yes, You Can Still Travel to Cuba

by Billie Cohen | June 5, 2019

The ways you can travel to Cuba have changed, but that does not mean you can’t go.

The change in Cuba travel restrictions that went into effect on June 5, 2019, alters the way travelers can visit the Caribbean island—but it does not mean travelers can no longer visit Cuba at all, or that they necessarily need to change their current plans. Cuba travel is still allowable, still legal, and still possible.

Big travel news like this can initially seem alarming and definitive. However, it’s often the case that if you’ve arranged a trip with the right planner, you’re not likely to be affected at all. That’s because smart, well-connected, and well-informed custom-trip designers—like those who’ve earned a spot on Wendy’s WOW List—have ways around all those problems that affect everybody else who isn’t using the right local expert. As just one example, that was the case with the 2016 hubbub that Italy’s Cinque Terre was becoming so crowded that authorities were going to require tickets. In actuality, they weren’t, and savvy Italy trip designers were already providing their travelers with crowd-avoidance itineraries anyway.

That’s the case with this latest Cuba news. Case in point: David Lee, Wendy’s recommended WOW List travel specialist for Cuba, won’t have to change a thing about the way he plans his custom trips to Cuba. So anyone who organized a trip through him (or who wants to in the future) can continue not only to experience Cuba, but to experience it in a way that the cruise masses and large tour groups never could anyway.

Here’s what’s going on:

There are several categories of legal travel to Cuba (religious, diplomatic, school groups, etc.), but the two that affect most visitors are called “Support for the Cuban People” (unaffected by the new restrictions) and “People to People” (ended by the new restrictions).

Still Allowed: “Support for the Cuban People” Travel

Whereas the People-to-People category was supposedly based on fostering educational dialogue and was used by large groups, the Support-for-the-Cuban-People category is for independent travelers and is about supporting the Cuban locals. (As we’ve learned from many of our readers who’ve reported back to us, this kind of travel actually fosters much more educational dialogue.)

Support for the Cuban People was and still will be used by independent travelers and custom small groups, all of whom must follow specific guidelines for their itinerary. As WOW Lister David Lee explained in an email, “The U.S. ban on general tourism to the Caribbean island was in place even after the lessening of restrictions under the Obama administration, which meant ‘tourism’ was not/is not a valid reason to visit Cuba.”

So while travelers in this category can’t spend too much time at the beach, they can arrange to have much more rewarding experiences and interactions with locals—such as touring Havana with renowned photographers and having a one-on-one discussion with the city’s lead architect. “Our itineraries are curated in accordance with OFAC’s Support for the Cuban People guidelines but are customized to our travelers’ specific interests and preferred travel pacing,” David says.

He adds that his company takes care of all the logistics for U.S. citizens too: organizing a pre-approved schedule, keeping a record of appointments, securing all visas, organizing receipts, and storing all of this documentation for the required five years.

No Longer Allowed: “People to People” Travel

This category refers to non-academic educational and cultural trips, such as those offered by large-group tour companies and cruise lines. The Obama administration made this category more accessible by loosening the requirements on paperwork and licensing for tour operators, cruise lines, and commercial airlines. As a result, more than 2 million Americans visited Cuba this way.

As of June 5, however, this category of travel is eliminated. That means two things. First, cruise ships won’t stop in Cuba anymore. Cruise lines are currently making announcements about how they intend to deal with this. For instance, the Carnival Sensation‘s planned call in Havana this week will be replaced by a stop in Cozumel. Norwegian Cruise Line’s Norwegian Sun will be rerouted to Nassau. Travelers who work with a knowledgeable cruise planning expert (see The WOW List for Wendy’s recommendations) are already a step ahead of the pack: These specialists have strong relationships with cruise lines and encyclopedic knowledge of ships and itineraries, thereby making vacation alterations easier and less painful.

Second, large-group tour operators will no longer be able to lead trips. However, travelers don’t see Cuba this way. That’s not how we recommend visiting. Instead, they’re traveling via the previous category.

The upshot:

Go to Cuba, learn about the country and its people, and do it all in a way that is both legal and rewarding. Start with The WOW List and let us know how it goes!


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