Viva Cuba! How to Get to Cuba: Part 1 – Introduction & Planning

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Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers. Emily:  When I learned about America’s more relaxed policy towards travel to Cuba, I jumped at the opportunity!

Cuba has a lot to offer.  My friends and I were drawn to the classic cars, the Art Deco architecture, and, of course, the friendly people!  We also love music and dance, which is one of Cuba’s specialties! Rick Steves recently produced an excellent video on Cuba that’s fun and informative.

The US and Cuba reached an agreement for direct flights.  Flight availability to Cuba from various US airports and search engines is ALWAYS changing, so be sure to try multiple search engines and cities, if possible.  Readers have reported that some flights to Cuba from the US may be opening up.  When I went to Cuba in December 2015, flights were not scheduled yet. My friends and I flew via Cancun, and continued our journey to Havana. Note:  Regulations surrounding US travel to Cuba are always changing, so make sure you check the current rules before planning your trip.  There are limited opportunities to use miles & points, but you can save some money.  I’ll show you how later in this series!
Viva Cuba How To Get To Cuba Part 1 Introduction Planning
A Trip to Cuba Feels Like Stepping Back in Time! The Architecture, Classic Cars, and Fascinating Customs Provided Me With Gobs of New Experiences!

My travel partners included many of the same friends who accompanied me to Croatia!

Robbie (pink hair) is a professional dance instructor who teaches salsa, kizomba, and bachata.  Sarita is also a dance teacher, as well as a graphic designer.  Gissell teaches fitness classes and loves rock climbing.

On this trip, I went with 3 new friends – Diana, a local art teacher, Chelsea, who manages a hostel, and Antonio, who works in IT design.  Traveling as a group of 7 was fun, but definitely challenging at times!  We had a great time together, and can’t wait to return!

Viva Cuba! Trip Report Index:

The Basics – Visa Requirements

Traveling to Cuba requires some additional research and planning.  You will need to make sure your visit falls into one of the 12 categories for approved travel into Cuba, which are:

  • Family visits
  • Official business of the US government, foreign governments, and certain intergovernmental organizations
  • Journalistic activity
  • Professional research and professional meetings
  • Educational activities
  • Religious activities
  • Public performances, clinics, workshops, athletic and other competitions, and exhibitions
  • Support for the Cuban people
  • Humanitarian projects
  • Activities of private foundations or research or educational institutes
  • Exportation, importation, or transmission of information or informational materials
  • Certain authorized export transactions

I went to support the the Cuban people.

It was very easy to get a visa.  It costs ~$20 and is a separate piece of paper.  My passport was not stamped.

Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Cancun Was One of the Cheaper Gateway Cities to Enter Cuba

The Basics – Cash

Cuba does not accept American credit or debit cards.  So you’ll need to withdraw enough cash for your entire visit.  It might seem frightening to carry a lot of money with you in bills, but we didn’t experience any problems!  I kept my money in a safe in my casa particular (more on that later!).
Viva Cuba How To Get To Cuba Part 1 Introduction Planning
$1 Was Worth ~$1 in Cuban Pesos

I exchanged half of my euros at the airport and the other half at a local currency conversion shop.  I’ll explain why I exchanged euros later in the series.

The Basics – Internet

Internet can be hard to come by in Cuba.  Major hotels offer internet access, but it can be very expensive.

Our reader, Karen (thanks!), explained there are cheap internet options:

“[You can pay] 3Cuc an hour ($3 an hour) for a WiFi card at any of the WiFi parks located all over Havana. You walk by the parks and there will be tons of guys selling WiFi cards. 2 Cuc an hour if you buy it from the internet shop. You can use the exact same cards to use the WiFi at any of the fancy hotels (or right outside of them). How to find a WiFi spot? You’ll notice people sitting around on their phones and tablets, there’s WiFi available there. The WiFi isn’t the fastest and some sites (like Yelp) are blocked, you can’t work from home from Havana but getting online isn’t hard at all. I do agree that it’s often nice to disconnect.”
Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Finding a Wi-Fi Hotspot Is an EVENT!

I learned to detach from my phone and the internet, and it was the best decision I made in Cuba!  It taught me the importance of relationships with others.  I realized how frequently we get distracted by what’s going on with our phones.

Flights to Cuba

My friends and I flew Southwest from Austin, Texas, to Cancun.  I booked 1 month before my travel dates, and paid ~25,000 points and ~$75 in taxes and fees for a round-trip in coach.

We decided to stay a few nights in Playa del Carmen before heading to Cuba.

Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Flying to Cancun on Southwest Was Cheap and Easy

We had a lot of fun in Playa del Carmen, but next time I’d rather spend the extra days in Cuba.  There’s so much to see and do, just in Havana alone!  I was there for 9 nights, and it still wasn’t long enough to accomplish everything on my to-do list!

After our short stay in Playa del Carmen, we took a Cubana Air flight from Cancun to Havana.  The total cost to fly coach round-trip was ~$350.  You can’t use miles or points because Cubana Air is not part of an alliance.

I booked my flight with the Chase Sapphire Preferred card and earned 2X points for travel purchases.  I had no issues using a US-issued credit card, but your experience could be different. 

Where to Stay

Hotels are expensive at ~$100 or more per night.  Since the 7 of us are a budget-conscious crowd, the prospect of spending thousands on a few hotel rooms was NOT an option.  After thoroughly investigating cheap Cuban accommodations, my friends and I decided that staying in a casa particular (a local apartment) was the best idea.

What a great decision!  Our 3 bedroom apartment came with 3 full bathrooms, a dining room, living room, and garden room.  We paid ~$17 per night per person, making it a steal!  And staying together was fun too.

Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Who Knew Frugality Could Strengthen Friendships!?

The total cost per person for 9 nights was ~$149.  Cheap rentals are 1 of my favorite things about Cuba!

Where to Eat

The restaurants we tried around town were touristy, and the food wasn’t great.

The best meals we had were home cooked!  My friends and I had fantastic breakfasts at our apartment, with eggs, meat, bread, croquetas (kind of like hush puppies), fruit, fresh juice, and coffee.  We could ask for lunch or dinner whenever we wanted, and we would receive a home cooked meal.

Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Two Pizzas for the Price of Fun!

Later in the series, I’ll review some of the restaurants we did try, and share my favorites.

What to Do

I stayed in Havana for 9 nights, and I loved every moment.  Havana is so rich in culture and history!  You can easily spend 2 weeks there without seeing everything.  There is so much to explore!  Plus, the beach was a quick ~20 minute drive away.

Ride in Classic Car Taxis

Some of the most fun we had was riding in taxis!  Almost every Cuban taxi is a beautifully maintained classic car from the 40’s or 50’s.

Note:  Have an idea of what your cab fare should be.  Some drivers will massively over-quote you!
Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Ride to Your Destination in Classic Style!

Get To Know the Locals

Cubans are very warm and friendly people, and will go out of their way to help others without expecting anything in return.  I loved getting to know them and hear about life in Cuba.  They’re very relationship-oriented, and live in a society where people and relationships come first.

Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Meeting the Locals Is a Huge Part of the Travel Experience!

I loved to see that attitude!  Especially coming from the US, where independence is celebrated, and individual achievement is priority.  Relationships can be hard to maintain because of the demands of work, school, etc.  Being in a place where people craved human connection was therapeutic.

Shop for Local Art

Cuba is filled with amazing artists.  My friends and I had a fantastic time browsing the local art markets.  I ended up purchasing a beautiful painting, which now hangs over my sofa.  It was my greatest souvenir from Cuba!

Viva Cuba How To Get To Cuba Part 1 Introduction Planning
Cuba Is Bursting With Talented Artists

Take Day Trips to the Beach

The best beaches in Cuba are a ~4 hour drive from Havana.  But you can find beautiful beaches just ~30 minutes away, too!  My friends and I enjoyed piling into a cab to take an afternoon ride to the suburbs for an incredible sunset.

Viva Cuba How To Get To Cuba Part 1 Introduction Planning
We Liked Getting Away From Other Tourists and Enjoying the Beauty of the Cuban Shoreline

You Can Do It, Too!


Link:   How to Transfer Chase Points to Southwest

Link:   How to Earn the Southwest Companion Pass

It’s easy to get to Cuba via Mexico on Southwest Airlines.  Direct flights MAY open up to Cuba soon, so check to see which flights have the least expensive award seats.  Until then, I recommend going through Cancun or Mexico City.

You can get lots of Southwest points by transferring your Chase Ultimate Rewards points to Southwest!  And if you have the Southwest Companion Pass, you can bring a friend for (almost) free!  I also like that Southwest doesn’t charge for checking a bag.

To transfer your Chase Ultimate Rewards points, you must have either the Chase Sapphire Preferred® Card, the Ink Plus® Business Credit Card, or the Chase Ink Bold (no longer available).

You can earn lots of Southwest points by signing-up for the Southwest Rapid Rewards® Plus Credit CardSouthwest Rapid Rewards® Premier Credit Card, and the Southwest Rapid Rewards® Premier Business Credit Card.

And you can use the Barclaycard Arrival Plus World Elite Mastercard to erase the cost of your Cubana Air flight!


There aren’t any chain hotels where you can use miles & points, and hotels cost ~$100 per night.  But there ARE some Airbnb locations for rent, which can be covered with points from the Barclaycard Arrival Plus.

I stayed in a casa particular (more on that later!).

Here’s how to choose a good, safe Airbnb.  And read my tips on how to negotiate a better price!

Bottom Line

Cuba is one of my favorite countries because of the colorful energy, diversity, and history.  There’s so much to explore in Havana alone, and I can’t wait to return!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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