Airports, Airlines, Aviation

Flying to Cuba (HAV)

The next big trip I’m planning is flying to Cuba through Havana Airport (HAV) – this blog documents the process of getting there.

Flying to Cuba has been on my mind for a while now since the recent U.S. legislation has made it less illegal and easier to visit Cuba as a U.S. Citizen. The floodgates still haven’t opened completely yet – at the moment, U.S. carriers still aren’t flying directly to Cuba (foreign ones are – for example, British Airways has a direct flight to HAV from LHR) – and it’s still not totally “legal” to travel their as a U.S. tourist unless you fall into a special category.

Cuban Flag

In fact, when you go to the U.S. Department of State website – here’s what you’ll find about flying to Cuba:

TOURIST VISA REQUIRED: Tourist travel to Cuba is prohibited under U.S. law for U.S. citizens and others under U.S. jurisdiction.

Here’s what’s changed as of May 5, 2015 – if you’re flying to Cuba and you fall in to one of these categories, you have approval from the U.S. government:

OFAC has issued general licenses within the 12 categories of authorized travel for many travelrelated transactions to, from, or within Cuba that previously required a specific license (i.e., an application and a case-by-case determination). Travel-related transactions are permitted by general license for certain travel related to the following activities, subject to criteria and conditions in each general license: family visits; UPDATED MAY 5, 2015 2 official business of the U.S. 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 information materials; and certain authorized export transactions.

You can read more about what’s specifically authorized and not authorized regarding flying to Cuba here.

Any day now, the U.S. Government is going to officially permit tourist travel to Cuba – it’s speculated that will come by the end of 2015. This is one of the main reasons I wanted to get to Cuba now – see it before the masses descend on the island and its character dramatically changes. Now is as good a time as any of flying to Cuba, even though it takes a little extra work, planning, and money to make it happen.

Namely, you still have to fly in through a third country – even though the island is 90 miles off the coast of Florida, the best way of flying to Cuba today still is through Mexico (MEX), Panama City (PTY), or Bogota (BOG).

The second reason I’m choosing to go to Cuba is that I’ll actually be on one of the A-B-C islands off the coast of Venezuela for the week of Sep 7th. I’m travelling to Curacao to lead a workshop for some of our travel distributor partners in the Caribbean region.

Since I’ll already be regional, I figured – let’s make the most of the trip and make it a “bleisure” trip (blending business and leisure) – and use it as an excuse for flying to Cuba.

Once that was decided, I asked Dave if he wanted to join me for the Cuba piece and he said yes. So, we spent the better part of Saturday making the flying to Cuba piece happen.

For the rest of this blog, I’ll share our strategy so that, you too, can more easily get your flying to Cuba underway.

I had initially done a bit of planning prior to booking…just to see what our options are and what the third city we would have to use for flying to Cuba would actually be, as well as ballpark costs.

My current Curacao trip is Monday, Sep 7 – Monday, Sep 14. I can adjust this as needed.

My workshop is Wed/Thurs/Fri (Sep 9 – 11), meaning I could fly out of Curacao to *somewhere* Sat morning, Sep 11. I would definitely have to fly from Curacao via a 3rd city to get to Cuba:

  • Bogota (BOG) (via Avianca Airlines)
  • Panama City (PTY) (via Copa Airlines)
  • Mexico City (MEX) is not an option because I can’t there directly from Curacao – would have to fly through Miami. Although, coming from the US it would make a lot of sense to fly via MEX – there are some very cheap flights both out of MEX and out on CUN (Cancun) that get your HAV same day on AeroMexico and Interjet (tripchi CTO Eli flew Internjet from MEX to HAV a few months ago).

I priced out these two options and the best price and time is on Copa Airlines (COP) via PTY – either way was a win for me as it would cross another country off my list (40+ and counting). I found a cost effective way to actually spend a few nights in Panama on the return from Cuba. I would just move my flight from Curacao to fly out of PTY instead on Saturday, Sep 19. So, here’s what we ended up doing for PTY-HAV and back, costing us a total of $1,198.58 for t pax:


Incidentally – it was cheaper to buy a roundtrip CUR-PTY flight and not use the return leg than actually just book a one-way from CUR-PTY. So, I decided to book the return leg as far in the future as possible that Copa would allow, and who knows – maybe I’ll return to the region in a year (Jul 23, 2015)!


These flights ran me $517.50.

Dave decided to book roundtrip with American Airlines from DEN – PTY and back $470/10.

And I also called American and had them change my return leg to match Dave’s on Sep 19, so here’s what my itinerary in and our of the region looks like:


This cost me $145.50 to change the itinerary – $200 for the change fee and then a little bit of a refund since the PTY-MIA flight was cheaper than the CUR-MIA flight, and inclusive of a $25 processing fee for calling the American Airlines desk. I probably could have done it through my work travel agency and gotten the fee waived, but I didn’t want to wait until Monday.

Here’s how the costs broke down for Dave and me:

CJ: $145.50 + $517.50 + $599.29 = $1262.29

Dave: $470.10 + $599.29 = $1069.39

I ended up paying a little more since I had to buy that unecessary return leg to CUR, and also because of the change fees for my work flight. Basically, flying through CUR added cost and complexity – and I don’t recommend doing this if you’re thinking of flying to Cuba. Fly out of MEX, CUN, PTY, or BOG, and it will save you money. Another side note – Frontier flies from DEN-CUN and Southwest will soon, so these will make your costs go down even more.

Side note – booking the Copa flights was a huge pain in the ass. The Copa Airlines website is not good, and putting together multi-city itineraries is a challenge. It was easier to price things out separately as outbound returns and not calculating multi-city stops. Also, when I went to book the PTY-HAV roundtrip on Copa, I decided to do a book and hold – meaning, I would hold the booking for 48 hours and put my payment info in at a later time. This seemed like a great option because it would allow us some flexibility in case some of our other flight legs didn’t line up the right way or became sold out, since we couldn’t make all the bookings simultaneously.

Doing the book and hold turned out to be a colossally bad idea. I entered in  my credit card info and the address associated with the credit card, but the payment kept failing without any easy to understand reason as to why this was happening. I figured I just fatfingered something. So I tried three times and got three failures. After the third attempt, a screen popped up that said my booking was cancelled and the payment was denied. I started to flip out. not only was it midnight when I was adding my credit card (after a few tequilas), but when I re-ran the search for flights from PTY-HAV, they were coming up $300 more expensive. I was livid, and didn’t know what to do, so I called Copa directly to get it sorted out. I was on the phone with an agent for about 45 minutes, and it took him 10 minutes each time I gave him a credit card to try (I actually thought he hung on up on me or the line went dead, but luckily I waited long enough and he came back on).

Both of my Citibank Mastercards failed again when he tried them – so at that point I realized my bank was blocking these charges, thinking they were fraudulent. At some point I got a text from Citibank asking me to authorize or reject a charge – so I hit authorize, thinking that this would unfreeze the card. But when the agent tried it again, it still didn’t go through. As I was on hold with the agent, I called Citibank to try to unfreeze the cards (incidentally, I had to go through this exact same process a few weeks ago when I was making a purchase at a Lowe’s in Virginia, and Citi blocked my cards). Someone at Citi answered, and I asked to unblock my cards, and he said the entire system was down and that I would have to wait three hours. That was totally unacceptable – what good is a credit card if you have to wait three hours to use it?

Luckily, I still had one final credit card I could try – Chase. So, I gave the agent that card, and while I was on hold called Chase to make sure the charge would go through – the Chase agent put an authorize payment on the card and also put a travel advisory for the time I would be overseas on the card so it wouldn’t go dark when I needed it then either. The Copa agent informed me the charge had gone through, so all was right again in the world – until I saw the $50 agent assist charge show up on my Copa receipt. So basically, Citibank screwed me majorly and the act of blocking my card cost me a $52 processing fee through having to call the airline (and Copa didn’t tell me that this fee would be added, a point I called to complain about the following day).

I came off of this process triumphant but livid, and made a note to call Citibank the next day and give them piece of my mind.

So the hard lesson learnt I would leave with my readers is – always, always call your credit card company before trying to process your credit card through a foreign airline carrier. It will save you time, money, and peace of mind.

Now that flying to Cuba is happening, we get to start the fun part – trip planning! Please leave me any tips as comments to this blog, or tweet to me @tripchi with your best Cuba advice. Hasta luego!

10 responses to “Flying to Cuba (HAV)”

  1. Hey-My first trip to Havana, too! I’m holding a #Havana #Hackathon Sep10-12. I’ll be staying a few more days after. Meet me and have some great stories for your Blog. The above website will list where I am up to the minute, so yoiu can easily find me. See You in Havana!

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