March 31 – April 1: Getting to Cuba

President Obama, through executive action, has recently removed many of the travel restrictions to Cuba. This, however, doesn’t mean that there aren’t any restrictions and that you can just go on Expedia and book a ticket from any U.S. city with an airport straight to Havana (it’s possible to book your ticket through a travel agent, but the one I tried immediately asked me about the license I’ll be traveling on. The link I included above is not the agent I tried).

Navigating the system can be tricky, and things change fast, so if you live in the U.S. (even if you hold a foreign passport, I believe…  Don’t quote me on that, but I read somewhere that travel restrictions apply to all U.S. Persons, not just Citizens. Do some more research if you fall into this category), you may want to go straight to the OFAC website (you can pronounce it any way you’d like) and read all the fine print. Here’s the latest Fact Sheet (published April 21, 2016).

Or you can just defy the embargo and go.


Here’s a good guide on How to Travel to Cuba Without a License.

Personally, I am very uncomfortable with breaking the law, so I wanted to do this right. I considered which license I could travel on. Journalistic? Not unless I’m employed by a news reporting organization. Humanitarian or People to People? I would need to go on an organized humanitarian tour or, if going on my own (and I’m not quite sure if that’s even an option), would need to keep a detailed schedule of all the official activities. Religious? LOL. Not wanting to trick the system within the system, I decided to go without a license. (My previous two trips to Cuba were all legal, with a license and with a group. I enjoyed those trips very much, but still felt like I haven’t really experienced Cuba. For me, real travel is not on a tour group, going by tour bus from hotel to hotel.)


This was a personal decision on my part (I could face up to 10 years in prison and up to $250,000 fine for biking on my own?!), and I’m in no way advocating for others to take the same risk. But let’s be honest…  Many Americans go to Cuba this way. I wish I knew how many, but Cubans don’t keep track (when going through Cuban immigration you won’t be asked for a license and your passport will not be stamped) and not many are self-reporting.

So I decided to go through a “gateway city”, Cancun, Mexico. There are several flights from Cancun to Havana per day. A few are on AeroMexico and I believe only one is on Cubana, a Cuban airline. I went to the Cubana website and booked my flight directly from them. To Cancun I booked through either Orbitz or Expedia (I usually go with either one).


It took me two days to travel from Seattle to Havana. On March 31st I left Seattle around noon (with a layover in Dallas) and arrived in Cancun around 9pm.

I spent the night at the Comfort Inn near the airport (not all that comfortable), which offers a shuttle service to and from the airport, but you must book it 24 hrs in advance. I didn’t do that and paid $25 each way for a taxi. That’s $50 for transportation that takes you approximately 3 miles beyond the airport parking lot… Just an FYI when considering your Cancun accommodations.

On April 1st Cubana flight was leaving around 4pm, so I had pretty much all day to stare outside my window from the “Comfort” Inn.


The taxi drivers congregating outside the hotel were only mildly entertaining and at 11 am I decided to take my chances and head on over to the airport, hoping beyond hope that the Cubana counter will be open and I’ll be able to check in my bike and my duffel bag (with my bike panniers in it).

The counter wasn’t open (it opened around 1 pm), so I spent two comical hours dragging my bike bag with one hand and my duffel bag behind me with the other (while carrying my carry-on) from the Starbucks to the bathroom and from the bathroom to the Guacamole Grill (surprisingly good for an airport joint) and back to the bathroom again.

As soon as the Cubana counter opened I checked in my bags. Here’s my shoutout to Cubana: Although they’re notoriously late (more on that soon), they have very courteous staff and they don’t charge for checked in luggage! Not even oversized luggage (compare that to the $241 I paid to United Airlines on my way back). And they make travel to Cuba, especially for Americans, very easy. As I was standing in line, an agent came up to me and asked if I needed a visa. I obtained a Cuban 30 day visa for $25 while pushing my bags through the line.


But don’t expect Cubana to be punctual. Like everything else in Cuba, it operates on the more fluid “we get there when we get there” schedule.

The flight was scheduled to leave at 4:05 pm. At some point it was announced to be DELAYED and the time was changed to 5:05 pm. The weather was great, so it wasn’t because of the weather.

In the meantime, I met two of my travel companions. Nedene and Jo were two of the women who comprised our biking Cuba trip. There were five of us all together (my other traveling companions were Mtn Val and Stuart; we met both the next day in Havana) and none of us had met each other previously. We all connected, with Nedene’s help, through Adventure Cycling Association.

Since our flight was delayed Nedene decided to do some airport shopping, but that’s when Cubana changed its mind and decided to board anyway. It wasn’t even 4:30! So I went in search of Nedene, found her and we ran back to the gate. Out of breath we were the last ones to board. Or so we thought.

After boarding we all sat at the gate for close to an hour. At 5:20 it was announced that the plane was waiting for two more passengers. WHAAAT?! No plane ever waited for me!

The two Cubans showed up around 5:30 (with bags from the Duty Free) and gave a friendly wave to the other seated passengers (they were in the row right in front of mine). People around me greeted them with wide smiles and waves in return.

Welcome to Cuba.



3 thoughts on “March 31 – April 1: Getting to Cuba

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