Many of us have romanticized travel to Cuba. We often don’t because of the unknown. We did in May of 2017, and it was terrific. Cuba is rich in history, culture, safe, inexpensive, and unique. It’s not the typical Caribbean most Americans are accustomed to, but that’s what makes it special. Cuba is not for a novice traveler because you need to know plenty before your visit to ensure a smooth trip.

We were lucky enough to travel to Cuba before the Trump administration tightened the economic embargo on Cuba. What this meant was that we were able to organize our trip independently. Under the new rules, Americans will no longer be permitted to visit Cuba on individual “people-to-people” visas. They are implying that Americans visiting Cuba will once again have to go through authorized tour operators. As with all laws, it’s subject to interpretation. You can still legally travel solo to Cuba under these visa categories. The standard visa people are using is “Support for the Cuban people.” The key is you have to know what you are getting into and do the research first.

This post may contain affiliate links. Please read our disclosure and privacy policy for more information.

Flights to Cuba

We paid $47.06 per person round trip from Orlando to Havana. This included a checked bag on JetBlue over Memorial Day 2017. How? We used 1,600 JetBlue points each way.

  • We earned those points from our trip to Dubai and South Africa on Emirates and converted them to JetBlue.
  • Don’t have JetBlue points? Convert AMEX points to JetBlue Points.
  • Don’t have AMEX points? Pay the regular price without points ~$155 round trip.

You can still fly to Cuba, but you must have a valid visa.

Visas for Cuba

As of June 4th, 2019, there are eleven visa categories you can travel on.  The “people-to-people” category that we used is no longer an option. Most people are using “Support for the Cuban people.” A general license means you do not need to go through OFAC for permission or any application process. You choose this category license and self-license yourself with it. If you select this category, this is what you need to know: § 515.574 Support for the Cuban People. Stated, you must engage in a full-time schedule of activities. And, you must keep a record of all activities and receipts for five years.

If you research what full-time means, you will find a variety of answers and debates. Most seem to agree that 6 hours a day constitutes full-time. There are plenty of options for organizing activities that meet this requirement.


Where to Stay When You Travel To Cuba

Let’s assume you have navigated your way to Cuba on a valid visa. You cannot stay in a hotel run by the government. This is because all the hotels are run by the government (this is part of the new restrictions). We stayed in a fantastic Airbnb in Havana by the Meliá Cohiba hotel. Our host arranged our private driver, which saved us a headache as we were in trusted hands.

Book your stay through Airbnb: And, claim $65 off your first stay!

If you are not traveling on an American passport, you can book hotels here:


There are two types of currencies, Cuban Convertible Pesos (CUC) and Cuba Pesos (CUP or M.N., for Moneda Nacional). CUC is the currency Americans will need to get, while locals use Cuban Pesos. Be prepared to pay a 10% tax. Many advise converting the dollar to euros because there is no tax on euros. You would need to do the math as you will pay fees to convert dollars to euros.


  • Do not convert money at the airport in Cuba; the lines are hours long. Jump into a pre-arranged private driven car and head to the nearest Cadeca (currency exchange).
  • Do not be intimidated by the look of a Cadeca. They are essentially storage pods with a window but are safe.

Important Information About Travel To Cuba:

You cannot use American-issued credit cards anywhere in Cuba. I’ve read on tons of sites that some places will accept them, and they just won’t. We ran into many people who had to have cash wired because hotels or others told them they could use their credit cards. Not so, and you will be stranded. Consider that if there was a place accepting them in 2017, we did not come across them. Given the tightened embargos, I doubt any business will take the American credit card because they are almost all government-run. You must bring enough cash with you to cover all possibilities, period.

Internet and Wi-Fi

You must buy government-issued phone cards for phone calls or Wi-Fi. We bought cards at the Meliá Cohiba hotel. We also found that this was the only place to get a connection, which was a challenge and a blessing – it forced us off the grid. I can’t recall the cost of the cards, but it was minimal.

Health Insurance

The Cuban government requires all visitors to have health insurance covering Cuba’s territory; this means local Cuban health insurance. If you purchase your flight through JetBlue, Cuban health insurance is provided by ESICUBA and administered by Asistur and is automatically included in your fare’s cost. Given that we traveled on JetBlue, our health insurance was included. I did check our American policies, and Cuba is not included! So be sure to check with the airline you are traveling with or buy insurance. Interestingly, while we had a printed copy of our policy, no one in customs reviewed or ever asked for it. I’ve heard this from several travelers, but I would not change it.

Getting About, Sight Seeing & Food

Hire a private driver. It’s not expensive, and you can go where you want when you want. Here are some of the things we did:

Havana Beaches:

We drove to a public beach Santa María del Mar, and spent the day. We drank all day, ate there several times, and could not spend $50 if we tried! The water was the bluest I have ever seen – hands down. The only thing that spoiled this was that the trash cans were overflowing, and there seemed to be no regard for litter. Looking back, while it was a fantastic day out, I wish we had chosen to go to a private resort because the trash bothered me. We were only in Cuba for five nights. If we had more time, we would have spent a night in Varadero, two from Havana. There are many private all-inclusive resorts in Varadero.


Plaza de la Revolución

Everyone goes here; we did a couple of times as almost every tour passes through. It’s a must-see but a quick-see. For me, the idea of being there in person was alluring and compelling. Understanding how Castro came to power, how the country has operated since then, and so on – know this is not a “day out.”

Classic Cars

If you travel to Cuba, you must take a ride in a classic car. You can pick your color, style duration, and tour. We chose a hot pink 50’s convertible and had a blast. I would have to guess this is on everyone’s must-do in Cuba as we all associate classic cars with Cuba.

Travel to Cuba

Old Havana

We spent a half-day in Old Havana, taking in all the sites. There’s plenty to see down there and tons of old cars. Restaurants line the streets with bands playing in most. You will feel like you have stepped back in time. Food-wise, we got unlucky due to a water outage. Only a couple of restaurants were serving, based on the availability of water.

Hotel Nacional de Cuba

We toured this hotel because it’s a national landmark. It’s where all of Hollywood used to play. Grab a drink and head to the lawn to watch the sunset over the fort. People will tell you it’s expensive for Cuba – it is but worth it. Following the evening, we ate at the Luxury restaurant Comedor de Aguiar, which I highly recommend. It was like a scene from the Titanic, and the food was well worth the cost. You can expect to spend about $40-$60 per person without drinks. This is not extreme by U.S. standards, but a similar meal elsewhere will cost you half this.

Third World

Cuba is a third-world country. The infrastructure is from the ’20s, and it is run down. Buildings are crumbling, the streets are not necessarily clean, and you’ll encounter stray dogs, dog poop, among other unsightly stuff. The grocery stores are bare except for rum! Unless you want to buy rum, potato chips, or water, stay away. You can smell the years of rat urine in the store. I know it’s rat urine as Brain does pest control for a living. It was rife. We stayed in the posh part of town. When we arrived at our digs, we thought we were in Beirut. I will be honest, for the first five minutes, we were concerned. The neighborhood was safe, the locals were wonderful, and never once did we feel unsafe. The entire street lost power at one point; we walked several blocks in pitch darkness and felt safe.

We experienced 24 hours with no water due to a significant break in the system (the entire street’s network). For us, that’s neither here nor there. We just went and bought water and took a shower in an old-fashioned way. My point is these things out is we expected most of this. We did not go in planning a 5-star luxury holiday. Almost every meal we ate was great, the food was cheap, and the drinks are “knock your pants off strong” along with silly cheap. So strong that I asked for the drinks not to be so strong, which rarely happens. The restaurants’ bars all have local entertainment, and we enjoyed our nights out and met loads of people.


Closing Thoughts on Travel to Cuba:

Everyone we met had a story about how they ended up in Cuba, along with their unique twist on their experience. Remember I mentioned people were stranded without cash? We met several who had rich stories to share. Cigars are everywhere but stick to the hotels for the real deal, as the streets are flooded with fakes. My favorite thing about this trip is it was full of surprises and learning. Learning how people in Cuba thrive despite hardship, the political conditions, and the cultural norms. Despite the third-world elements, Cuba is stunning! Time stands. Still, you must adjust to appreciate the beauty and go with the flow. We wanted to experience the culture, and we have no regrets at all! Will we go again? It’s a 30-minute flight for us!

Looking for more posts to inspire you? Start here:

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites.

Click Here To Subscribe

Subscribe to our newsletter now and get the best travel tips and inspirational stories delivered to your inbox every month. No spam, no sales pitches –  JUST TRAVEL!

Click Here To Subscribe

Travel Planning Resources

Looking to book your next trip? Use these resources that work:

  • Book your Hotel: Find the best prices on hotels; use for the best deals.
  • Book your Flights: Find the best deals and prices on flights; for the best deals.
  • Find Apartment Rentals: You will find the lowest prices on apartment rentals with’s Apartment Finder.
  • Travel Insurance: Don’t leave home without it. Review our Travel Insurance Guide on how to pick and decide which travel insurance is right for you.

Are you interested in Volunteer Vacations and Working Holidays? Check out the complete guide to how here!

Need more help planning your trip? Make sure to check out our Resources Page, where we highlight all the great companies that we trust when we are traveling.

Share with others!