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

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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!

Flights

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 Airlines Rapid Rewards® Plus Credit CardSouthwest Airlines Rapid Rewards® Premier Credit Card, and the Southwest Airlines 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!

Hotels

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!

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

  1. So excited about this series!! Any idea when SW or JetBlue flights will be posted? We have been checking and calling almost every day. Planning to go this December. American is expensive and would rather go SW or JB and points if that ever happens.

  2. Have my trip booked to Cuba in October, so I’m looking forward to this series. I’m curious what the language barrier was like?

  3. i would love to go to Cuba after the end of the abuse etc by the Castro bros….

  4. There’s a fair bit of misinformation in this post.

    Don’t take US dollars, at least not right now, you’ll be hit with a 10% fee when you change money. It’s MUCH better to take Euros or Canadian. You want mainly convertibles with a small amount of national money if you want to buy anything off the street (fruit, pastries, etc). There are 2 types of currency in Cuba and you NEED to be familiar with both to ensure you aren’t ripped off with change since the national money is worth far, far less.

    “Almost every Cuban taxi is a beautifully maintained classic car from the 40’s or 50’s.” – while the old car aspect is true the beautifully maintained part is not. I’ve ridden in many a taxi in Havana, all over Cuba, and I’ve never had a beautifully maintained old car. The only ones that are are the tourists cars which cost way more than a regular taxi. The regular taxis are rough and beat up. It is amazing how they keep them running, rough as they are. I’ve seen replacement dashboards and steering wheels carved out of wood!

    “My passport wasn’t stamped” – this is hit or miss, I have never NOT had my passport stamped. Not having it stamped has never been an option so don’t plan on this.

    “Internet is hard to come by” – Nope, not at all. 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.

    “The restaurants we tried around town were touristy, and the food wasn’t great” – oh my……while I would NEVER say ‘don’t eat at your casa” because every casa meal I’ve ever had has been amazing and it’s usually way more food for a fantastic price, there is INCREDIBLE food in Havana. Los Nardos and Dona Eutima, are two of my favorites and judging by the lines of people eating there (not all tourists), I’m not alone. There are wonderful paladars all over the city and easily found with a google search or even looking in a guidebook.

    The TripAdvisor Cuba forum has a wealth of information from very knowledgeable people

  5. @Drew R – you’ll need at least some Spanish and a phrasebook. English is not commonly spoken, even in the tourist areas. If you do have people who speak perfect English come up to you on the street they are looking to run some kind of scam.

  6. @Nina- I don’t know when the airlines will start operating there. You are smart to be checking. Maybe it would help to call customer service and see if they could help further? Good luck!

    @ Drew R- It does help to know at least a little but of Spanish. Some people do speak English, but with any foreign country, how much you can immerse yourself in the culture can depend on how much of the local language you speak (and vice versa). There’s always things you can do with no language barrier, such as enjoying music and dancing!

    And Karen was right—Cubans do look for ways to make extra money. I found it OK to be a bit more generous with some people because of their kind spirits. But with anywhere you travel, it’s important to look out for people who just want to take advantage of you. And knowing at least some Spanish will help Cubans respect you more, and therefore will be less likely to take advantage of you.

    @ Karen- Thanks for pointing out these things for our readers! I only spent 9 days there, so I still have a lot to learn!

    I converted Euros to CUC, and have corrected the post. Thanks for pointing out this error. I did know about the added fee which is why I brought euros.

    I think the cars are beautifully maintained. They look gorgeous to me, and it’s OK if they have replacement parts. I found this part of the “realism” in Cuba that I grew to love. Life isn’t perfect all the time, and I appreciated the authenticism that Cuba displayed.

    As for the passport, I read reports that you can request to not have your passport stamped, and that Cubans agree to this. But I have not personally had this experience, so I don’t know for certain.

    Thank you for the internet tips! This would have been extremely helpful to know when I was there. I will update a future internet in Cuba post with this info.

    Also, thanks for the restaurant recommendations! Maybe the foodie in me was a bit harsh on the restaurant selection. Next time I return, I will have to check these out!

  7. @Karen – you are spot on with your response. I also believe there is now unbelievable gastronomy in Cuba. You have to know which paladars to go to, and the dining experience is excellent.

    @Emily – you stated you went for “educational activities and support for the Cuban people.” Under prior OFAC (Dept of Treasury) interpretation of the regulations, you cannot mix and match categories – you can only select 1 category. If you select support for the Cuban people, these must “include activities of recognized human rights organizations; independent organizations designed to promote a rapid, peaceful transition to democracy; and individuals and non-governmental organizations that promote independent activity intended to strengthen civil society in Cuba. The traveler’s schedule of activities must not include free time or recreation in excess of that consistent with a full-time schedule in Cuba.” I highly doubt you had a full-time schedule of such activities so you should keep records of your trip as a people-to-people educational exchange to qualify under category 5B. In addition, you must also keep a day-by-day log of what you did that constituted those people-to-people activities. The media portrays that all regulations have been opened between the US and Cuba when in fact, only little parts of the law have been relaxed. Email me for more info.

  8. @ Anthony- I was never asked by anyone about a schedule. Our trip included considerable time talking and learning with dozens of locals and educating ourselves about their history and current life. Another reader, Karen, (thanks!) commented that she’s been to Cuba and back multiple times and has never been asked about her schedule. And when I went through customs and immigration back in the US, I was never even asked which countries I visited (though I had the electronic customs screen).

  9. Emily – my friend just shared your blog post and I am loving it! I have been wanting to go to Cuba for years and I hope to make it there this fall 2016. If the US is delayed in getting flights down there my question is when you purchased your flight from Mexico to Cuba did you purchase here in the states or while you were in Mexico? Also is there anyway to direct message you?

  10. @ NC- I am so glad you are enjoying the series! Thank you for the nice comment. 🙂 I purchased my flight from Mexico to Cuba in the states. You can email me at emily at million mile secrets dot com.

  11. I just called AA. There is award availability on the 7th of September (inaugural), but it’s going to cost 27500 miles. Do you all think it’s worth the miles? I’m in the dilemma of whether I should just book the AA flights to Cienfugos or wait until the direct flights to Havana are released (which nobody knows when it will be)..Thanks!

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