You Can Fly To Cuba. But, Is Cuba Really Ready For You To Do That?

It seems like there’s been something newsworthy in regards to Cuba travel on a monthly basis for quite some time now.  The Obama administration started down the path of normalizing relations between the US and Cuba roughly 18 months ago and that started dominos falling towards commercial flights to Cuba.

Once the process began for US-based airlines to request the right to fly to Cuba, there were a ton of requests to begin service to both Havana and outlying cities.  In some cases, it was pretty surprising to see the size of the requests.  American was really thinking about operating 12 flights a day to Havana?  You had to figure these requests were inflated because the airlines thought they would be trimmed, even given American’s significant presence in Miami along with a strong Cuban population in that area.

The announcements of which airlines won what in the Havana lottery came out recently, and seem pretty fairly dispersed.

Now that we know who’s flying there and how often, how will things actually work?  We know that a few hotel chains are making inroads in Cuba.  I’ve suspected that it will be a longer process than these companies are hoping to get things up to their standards in other areas of the world, mostly due to such a lack of infrastructure in Cuba.  Your cell phone might work, but the service will be slow and expensive.

The unique indication here is that all the airlines are spinning up commercial service at the same time, and in a very short window, so there’s a lot of unknown.  Scott Mayerowitz of the Associated Press got an early look into how airlines are tackling this unique situation:

The Associated Press got exclusive access, joining American Airlines on a trip to Cuba to access the airports and meet with officials there.

“We have a good plan in place,” says Beltran, a longtime American executive who is overseeing the airline’s entrance into Cuba. “Even with the challenges, we have been able to look for loopholes.”

Take the baggage scanner. While some U.S. cellphones do work in Cuba, the U.S. SIM card in the scanner wouldn’t connect. So the airline found a workaround: get SIM cards from another country.


Internet speeds at airports are supposed to be at least 256 kilobytes a second — extremely slow but supposedly fast enough to process check-ins.

Then there is the unique cargo heading to Cuba. For instance, engine blocks are popular and, as JetBlue discovered, can be transported only if they never contained any flammable oils or fuel.

Because there are so many charter flights to Cuba right now, it hadn’t occurred to me that the airlines would still need that much ramp-up themselves to get moving.  I figured the airport itself would have huge growing pains, which I still anticipate.

The airlines aren’t the only ones having issues.  Unsurprisingly, the first of the chains to plant a flag in Cuba is dealing with teething issues.  Michael Weissenstein from the AP stayed at the new SPG property (Four Points) that was previously the Fifth Avenue Hotel.  To say it was a mixed bag would be generous.  A couple of excerpts from his stay:

Using Starwood’s website, I booked a “Classic Room” with king bed for two for $250. Testing Starwood’s invitation for special requests, I asked for extra pillows, water and a map upon arrival.

Starwood has been retraining staff at the Fifth Avenue, which it’s renamed Four Points by Sheraton Havana. The training shows: Check-in was remarkably smooth for a Cuban hotel. Front-desk clerks were solicitous and spoke fluent English. My fiancée and I got our key and headed to our room. It had two single beds instead of a king, and no water, extra pillows or map. The front desk quickly changed us to a room with a king.

But the rest of our experience was pretty unpleasant. The hotel had been rebranded with great fanfare a month earlier, including promised amenities like Starwood’s comfortable “signature beds.” But our mattress was saggy, with a stained decorative cover and flat sheet tucked over the sort of squeaky rubber pad used for bed-wetting children. When I investigated why a bedside lamp wasn’t working (due to a missing bulb), I realized that the entire wall-mounted light was loose and balanced in the sole position that kept it from collapsing…..

We went to the spacious terrace for cocktails and snacks. The shrimp cocktail wasn’t terrible: a handful of shrimp doused in Russian dressing in a martini glass filled with lettuce. But the menu dated to around the hotel’s opening in 2010, when it was run by the Spanish hotel chain Barcelo. How do I know? Because someone had taped a little piece of paper with the “Four Points by Sheraton” logo on the front. When I pulled it back, it said “Barcelo.”

Unwilling to try our luck with entrees, we fled for an excellent privately run restaurant nearby, then stopped in the lobby for a nightcap.

I asked for an Absolut vodka, soda water and lime. I don’t know what came, but it wasn’t Absolut. It tasted of paint thinner and curdled my mouth.

When I complained to the bartender, she tasted and agreed it wasn’t Absolut but showed me the bottle and insisted no one at the hotel had filled it with a cheaper brand or adulterated liquor. She opened a fresh bottle of Finlandia and poured me a drink that tasted as advertised.

Fly To Cuba

 So, Is Cuba Really Ready For The Wave Of Americans?

I’ve been asking folks if they’re going to Cuba.  I assumed that there would be growing pains and scant resources along with the waves of Americans heading to Cuba.  Now that we’re theoretically within 90 days of commercial flights to Havana starting, things are still in disarray.

It may not be a crazy idea to go, but you do still want to be careful.  It’s not that you can’t have a relatively safe excursion without much of a plan (Seth specializes in these)but I’d generally advise a bit more caution.

It strikes me that there’s probably a narrow window to get to Cuba now before the thrust of people, where you’ll still deal with some poor conditions and strain on the infrastructure.  It also strikes me that given what we know today, it’s prudent to wait until a few months after commercial service launches to head to Cuba if you can’t get there before launch.  Once the commercial flights launch, I suspect it’s going to be a troublesome adjustment period.

The post You Can Fly To Cuba.  But, Is Cuba Really Ready For You To Do That? was published first on Pizza in Motion


  1. We’re heading to Cuba, not Havana, in Decrnber. We’ve decided that Casas particulates (guest houses) are the way to go. All our places have rave copious reviews on TripAdvisor and cost <$30/day.

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