Twists and Turns in Travel Industry’s Approach to Cuba Since Obama’s Changes

There have been numerous interesting developments and outright surprises since President Obama announced in late 2014 that the U.S. and Cuba agreed to begin normalizing diplomatic relations.

The latest head-turner was Thursday when Trump administration officials revealed that the president would announce Friday that the U.S. government is tightening travel policies toward Cuba but wouldn’t implement an outright ban of flights and cruises, for example.

Still, we have to introduce a note of caution here since, as with all things Trump, the policies could pivot on a peso tomorrow.

One thing in store is more aggressive scrutiny of whether travelers’ itineraries are consistent with the 12 permissible categories of travel, or whether the categories themselves will be rewritten when the fine print emerges in the next several weeks or months.

While there was a degree of initial euphoria that Cuba would become the next hot destination on the bucket lists of throngs of travelers when Obama and Cuba opened things up, it hasn’t turned out that way as the demand wasn’t there and the infrastructure was lacking.

Airlines scheduled new routes and then cut capacity; secondary cities that had seemed promising failed to attract enough demand to warrant flights.

There were some standup moments, too, as when Carnival Corp. announced it would delay sailings to Cuba unless Cuban-born passengers were allowed to board and cruise to their homeland.

Following are two dozen stories — all original Skift reporting — on how the business of travel has developed in Cuba over the last three years.

December 17, 2014
What President Obama’s Cuba Speech Revealed About Travel and Diplomatic Relations

April 7, 2015
5 Airbnb Cuba Hosts Manage Half of the Island’s Inventory

August 13, 2015
Cuba Looks for Edge Over Caribbean Rivals With Online Study of U.S. Tourists

September 24, 2015
Anthony Bourdain’s New Cuba Episode Shows an Island in Transition

December 18, 2015
Cuba’s Tourism Challenges Remain Clear One Year After Obama’s Announcement

March 19, 2016
Starwood Is First U.S. Hotel Chain to Receive Authorization to Operate in Cuba

March 20, 2016
Marriott Enters the Cuban Market Like Starwood and Airbnb Before It 

Skift Survey: 25 Percent of Americans Are Interested in Visiting Cuba Next Year

March 21, 2016
Booking.com-First Strategy at Play In Priceline’s Cuba Entry

April 13, 2016
European Tour Operators in Cuba Mull How U.S. Thaw Will Change Competition 

April 18, 2016
Carnival Will Delay Cruises to Cuba if Cuban-Born Passengers Denied Entry

June 20, 2016
How Tiny Silver Airways Plans to Win in Cuba and Beyond

June 30, 2016
Skift Podcast: Top Hotel CEOs and Executives Talk Direct Booking, Airbnb, and Cuba

August 2, 2016
The Only Thing to Stop Cuba’s Tourism Growth Is Its Accommodations Crunch

September 6, 2016
Cuba’s Hotel Challenges: A Guide to All the Projects in Process

Skift Global Forum Preview: Carnival CEO on Bringing American Business to Cuba

October 27, 2016
TripAdvisor Granted Permission to Sell Cuba Flights, Hotels, Tours and More

December 8, 2016
The 3 Largest Cruise Lines Can Now Take Tourists to Cuba. What’s Next?

December 21, 2016
Carnival Corp. CEO Says Cuba Is a Longer-Term Play

January 16, 2017
The Short Life of Fathom Shows Cruisers Mostly Just Want to Cruise

January 18, 2017
JetBlue Rolls Out Loyalty Program Incentives for Cuba Routes

March 13, 2017
Silver Airways and Frontier Airlines Are Giving Up on Cuba After Eight Months

March 20, 2017
Cruise Lines See a Tourism Advantage in Cuba and Hope Trump Doesn’t Ruin It

May 15, 2017
U.S. Travelers Still Want Cuba But Brands Were Too Aggressive Too Soon

June 2, 2017
U.S. Airlines and Cruise Lines Could Lose $3.5 Billion if Trump Reverses Cuba Policies