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How Americans Can Travel To Cuba
Adult Adventures

How Americans Can Travel To Cuba

Cuba sunset

Did you know that it’s still possible for Americans to travel to Cuba? Kasey Austin, President of Austin Adventures, just returned from a trip to this fascinating island nation and wants to share how she got there legally, as well as a few highlights from her recent travels between Trinidad and Havana.

We’ve recorded a webinar that is perfect for travelers and travel advisors alike to discover how you can have a life-changing experience in the “Pearl of the Antilles”!

Can Americans travel to Cuba legally?

As I made my way from Montana to Florida, I was bewildered at the number of people who exclaimed, “you’re going to Cuba? I thought that wasn’t legal!” I must have gotten this response 10 times from Uber drivers, hotel concierge, and even TSA agents at the Fort Lauderdale Airport. The answer is, YES! Americans can travel to Cuba from the USA legally.

With ever-tightening Cuba travel restrictions from the American government, it’s no wonder that Americans are confused. Here’s how I went about traveling to Cuba legally.

OFAC Entry Requirements

The Department of Treasury’s Office of Foreign Assets Control (OFAC) offers 12 categories of licenses under which Americans can travel to Cuba legally. Technically, you can’t just buy a plane ticket and travel to Cuba to sun yourself on the beach while smoking a Cohiba. You’ve got to have a reason to travel to our southernly neighbor that falls under one of these 12 categories. But unless you’re traveling with a religious group, doing a humanitarian project, visiting family, or going on an educational trip, chances are high that most of the license categories won’t apply to your Cuba travels.

Support for the Cuban People Travel License

The license category we’ve found that our program qualifies for is called “Support for the Cuban People.” Under this license, American travelers “must engage in a full-time schedule of activities that result in meaningful interaction with individuals in Cuba.” Basically, this means that you can book a trip to Cuba if you engage with the locals and participate in activities that will strengthen Cuban society. That’s pretty darn vague, but that’s a good thing because it leaves a lot of room for interpretation and a good amount of flexibility in an itinerary.

At Austin Adventures, we interpret “strengthening Cuban society” as supporting Cuban local businesses. We’ve searched out the locally-owned B&Bs for our accommodations; the finest private paladares for our meals; and the best connections for activities and experiences.

Unfortunately, just showing up to Cuba and figuring out your plans on the fly isn’t an option at this time. You’ve got to have your itinerary researched and laid out ahead of your Cuba

A Cuba Vacation with Austin Adventures

It might seem overwhelming to research and plan out a Cuba itinerary on your own with the current travel restrictions in place. But never fear, the experts in Cuba travel are here!  Austin Adventures has been navigating the ever-changing rules of travel in Cuba for nearly 8 years.

Our Cuba Vacation adheres to the regulations of OFAC and the “Support for the Cuban People” travel license category. We offer active, all-inclusive, small-group scheduled departures as well as customized vacations that provide meaningful interactions with locals as well as the comfort and safety you’d expect from traveling with a top-notch tour operator.

discover bliss in cuba

Kasey’s Opinion on Cuba Travel

This having been my first trip to Cuba, I can honestly say I was shocked and pleasantly surprised at not only how easy it was to get to and from Cuba, but also how welcomed we were by the locals at every turn. We work with a partner who has feet on the ground in Cuba, and you just can’t beat the experience of traveling through Cuba with local connections and expertise.

In this very complex and complicated country, I was overwhelmed (in a good way) at the knowledge our guide imparted on us and his good nature in answering our never-ending questions over the course of 8 days spent touring Trinidad and Havana by his side.

Our action-packed itinerary kept us quite busy and engaged, but was also balanced with time to relax at our luxurious B&B’s (yes, luxurious even by American standards!) I can’t imagine a better way to experience Cuba for the first time!

Of course, as a first-time traveler to Cuba, I have to share a list of my favorite experiences we had on our Austin Adventures Cuba Vacation.

Top 5 Things to Do in Trinidad

1.Hiking in Topes de Collantes National Park

Topes de Collantes is located in the Escambray Mountains and is accessed along a winding pothole-filled road. The 30-minute drive out of town is worth the bumpy ride. This natural park boasts excellent hiking trails through coffee plantations to backcountry waterfalls and remote swimming holes.

2. Salsa dancing at Casa de la Música

The vibrant atmosphere of Casa de la Música is something that will stick with me forever. Sipping on an ice-cold local Cristal beer while swaying to the rhythm of salsa music just screams Cuba! Don’t be afraid to bust-a-move on the dance floor alongside locals and tourists alike!

3.Horseback riding in Valle de los Ingenios

Take a trip back in time with a horseback ride through a UNESCO World Heritage Site. Valle de los Ingenios or “Valley of the Sugar Mills” is rife with historic significance dating back to times when Cuba depended on slaves for sugar production.

4. Tripping over cobblestones in Plaza Mayor

Trinidad is known for its historic cobblestone streets (which hold stories of their own) and there’s no better place to “twist an ankle” (a joke in my group) than Plaza Mayor – the main square. This beautiful slice of paradise is the perfect spot for people to congregate and admire the architectural beauty of the city center.

5. Relaxing at Hacienda La Casona

If we weren’t out exploring Trinidad, then it was most likely you’d find our group relaxing within the intimate walls of Hacienda La Casona. This working farm with horses offers dramatic views of the surrounding valley and is the perfect place to enjoy a mojito at sunset.

Visit Trinidad on your way to Cuba with Austin Adventures

Top 5 Things to Do in Havana

1.Bicycling around Centro Havana

There’s something to be said about traveling by bicycle through a city. An easygoing pace allows you to observe daily life happening all around you, smell the cinnamon churros on a local food cart, and listen to the kids yelling and singing at the primary school.  Plus, you can access sections of the city that you just can’t get to by car – sign me up!

2. Fine dining at La Guarida

Havana’s most legendary private restaurant sits in a location used for the Oscar-nominated Fresa y Chocolate film shot here in the 90’s. The pictures lining the walls tell the stories of visits from the rich and famous over the years. And the restaurant itself features both classic dishes and those that are unusual to Cuba. I recommend the ropa vieja (the national dish of Cuba), but really, you can’t go wrong with anything on the menu.

3. Musing over artwork at Fábrica de Arte Cubano

To find out why Fábrica de Arte Cubano is on TIME’s 2019 list of the World’s 100 Greatest Places, you need to check this place out yourself! This art factory is the hippest nightlife spot in Havana and features a top-notch restaurant, trendy bar, revolving art gallery, and live music that will entertain you and your amigos to no end!

4. Painting at Santacana Estudio Taller

The studio of artist Beatriz Sala Santacana is a bit off the beaten track but well worth the trip out for a look into a Cuban artist’s workshop. We set up a class for our group in the studio’s beautiful courtyard to paint acrylic designs on canvas and walked away with a unique keepsake of our Cuban travels.

5. Cruising in a 1950’s car along the Malecon

Of course, no trip to Cuba would be complete without a cruise in a vintage car! Even today, there are no shortage of cars dating back to the 1950’s lining the streets of Havana. With many tours to choose from, you’ll have plenty of options and even more opportunities to snag pictures of the local sights and a few selfies along the journey!

Bonus: As you travel between Trinidad and Havana, a neat stopover activity just outside Playa Larga is a guided kayak tour through the wetlands of Zapata Swamps National Park. I felt like I was on a self-propelled ride at Disney World as I navigated my way through a tunnel of interlocking mangrove trees. These wetlands also offer sanctuary to different species of invertebrates, reptiles, and birdlife.

luxury travel in cuba with austin adventures

If you need help or advice, give our travel experts a call!

There you have it, a personal guide on how to travel to Cuba legally as an American as well as a list of my favorite experiences from my own trip to Cuba in November 2019 (did I mention I just happened to be present for the celebration of Cuba’s biggest event: the 500th anniversary of Havana?!)

There’s no time like the present to visit this fascinating destination.

If you need help or advice, don’t hesitate to give our travel experts
a call at 800-575-1540!


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