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Trump Paves The Way For US Companies To Enter Cuba

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The executive order issued by the White House on May 1 has shaken Cuba’s foundations. The United States decided to tighten the noose around an economy that was already in intensive care even before the new sanctions that took effect on Friday, or the oil blockade implemented earlier this year. Washington’s threat to freeze assets on U.S. territory of any foreign company or individual doing business with the Cuban regime — especially with the vast portfolio of businesses held by Gaesa, the military conglomerate that controls half of Cuba’s GDP — has produced its first effects. And once foreign companies withdraw, their replacement by U.S. firms appears to be the next step.

Within weeks, two large Spanish hotel chains (Meliá and Iberostar) were forced to abandon part of their operations, giving up management of 15 and 12 hotels respectively that were owned by the Armed Forces. That withdrawal, however, will not spare them from lawsuits by the Cuban government, which will demand compensation for unilaterally terminating their management contracts. Canada’s Blue Diamond and Indonesia’s Archipelago International have also exited their businesses entirely, while the shipping lines CMA CGM (France) and Hapag-Lloyd (Germany) have chosen to halt container deliveries. The exodus has not only hit tourism, the main pillar of Cuba’s economy. It has also struck mining, which accounts for a third of goods exports. Canadian company Sherritt International, which had a joint venture with the island’s government, disclosed a nonbinding agreement under which Gillon Capital, a firm linked to a former adviser to Donald Trump, would acquire a 55% stake.

Business sources close to the Cuban government summarized to EL PAÍS two weeks ago what they believe is the sole objective of the U.S. sanctions: “They want to take over the Galicians’ business” [referring to Spaniards who emigrated to Cuba at the end of the 19th century].

The first candidates could be Marriott, the world’s largest hotel company with 7,781 hotels, and Airbnb, the largest short-term rental platform, with nine million listings. Both have already operated or currently operate in Cuba under special licenses granted by the U.S. government during Barack Obama’s second term in the so-called “Cuban thaw.” They have never concealed their interest in continuing to expand on the island. Between 2016 and 2020, Marriott managed the Four Points by Sheraton Havana, becoming the only property operated there by a U.S. giant. Arne Sorenson, Marriott’s former CEO, was one of the business executives who accompanied President Obama on the March 16, 2016, flight that marked the start of that new phase.

Airbnb, for its part, landed in April 2015 with 1,000 listings, but was restricted to hosting only U.S. tourists. In its first year it welcomed 13,000 travelers and the number rose to 35,000 listings by 2019, once an exceptional permission was granted to host non-U.S. guests as well. From there the numbers fell sharply because of successive economic crises and the pandemic, despite relief measures approved during Joe Biden’s administration. The final blow came from a Department of State order dated January 31, 2025, which restricted Cuba’s access to international banking and forced hosts to find alternative payment methods abroad, collapsing the business.

A devastating outlook for Cuba

The picture painted by these initial moves, together with those that may follow soon, is, at best, devastating. For Max Meizlish, a former Treasury Department official from 2020 to 2024 and a researcher at the Foundation for Defense of Democracies (FDD), this is unprecedented pressure. “Washington’s pressure aims to definitively turn the Caribbean country into a financial pariah, without external sources of financing. Right now, what we see is that all these strategic sectors of the Cuban economy that have touchpoints with foreign firms are being pressured for the first time,” he concludes in a Zoom call.

The onslaught arrives at a moment of extreme vulnerability. In recent years the Cuban government has implemented a severe austerity plan that includes cuts to public spending, a reduction of the bureaucratic apparatus, lower subsidies and an unprecedented increase in basic service fees, alongside a partial dollarization of the economy that operates with up to three different exchange rates. As an extraordinary measure, the regime decided to allocate budget resources month by month based on its revenues. Not to mention power outages that in large areas exceed 24 consecutive hours. “This is already worse than a wartime economy,” Cuban economist Omar Everleny Pérez says by phone.

Other experts point to two intertwined founding errors: betting everything on tourism and giving the military free rein through Gaesa, to concentrate economic power in accounts that cannot be audited by the state. In 2016, the military holding now targeted by Trump launched an ambitious hotel plan during the thaw with Obama in a bid to reach 100,000 rooms by 2030. “We cannot wait for the blockade [U.S. economic embargo] to end to build the hotel capacity,” President Miguel Díaz-Canel justified. For Pérez, those economic mistakes have put a noose around the country’s neck. Or, put another way, they have made Washington’s job of strangling the island easier.

The crux of the matter, says Max Meizlish, is that the executive order leaves the door open for the Trump administration to further expand economic pressure. Among the options available is pushing international banks to freeze funds of entities tied to the government and its military leadership. “What I would expect from any of these banks that want to comply with the terms of the executive order is that they block them. Make them feel trapped. And have those funds moved so they are inaccessible to the regime,” the former Treasury official says.

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Airbnb Wants To Run Your Entire Trip

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Airbnb is expanding beyond accommodation with new features like grocery delivery, airport pickups and trip planning tools. Credit : https://news.airbnb.com

Booking a holiday through Airbnb used to be fairly simple. You opened the app, found an apartment or villa, checked the reviews, argued with yourself about the cleaning fee for five minutes and finally booked the place.  Now Airbnb wants to handle almost the entire trip.

The company is preparing a major expansion that will introduce services like airport pickups, luggage storage, grocery deliveries, boutique hotels and even car rentals directly through the app. In other words, Airbnb no longer wants to be seen simply as a platform for holiday flats.

It wants to become the place where people organise everything connected to travelling.

And honestly, the idea probably makes sense for a lot of travellers.

Most people already spend half their holiday switching between different apps anyway. One for accommodation, another for taxis, another for activities, another for maps and usually several more buried somewhere in your emails containing booking confirmations you can never find when you actually need them.

Airbnb clearly thinks people are tired of that.

The app is starting to look more like a complete travel planner

Some of the changes are arriving this summer and they go well beyond accommodation.According to Airbnb, users will soon be able to organise airport pickups in around 160 cities worldwide. The platform is also adding luggage storage services for travellers arriving before check in or leaving hours after checkout.

Anyone who has dragged a suitcase around a city for an entire afternoon will probably understand why that feature alone could become popular very quickly.

Then there is the grocery delivery service.

Airbnb says guests in selected US cities will be able to order shopping directly to their accommodation before arriving or during their stay. So instead of landing late at night and desperately searching for an open supermarket, travellers could theoretically arrive to a fridge that is already stocked.

It sounds small, but it is exactly the kind of thing modern travel apps are increasingly trying to sell: convenience.

The company is also entering another area that feels much more ambitious : Car rentals.

Through the app, users will reportedly be shown vehicles available near their accommodation along with suggestions based on the size of the group or the type of trip being planned.

And because Airbnb wants people to actually use the feature, it plans to offer travel credit incentives for future bookings too.

Airbnb is also moving much closer to the hotel industry

For years, Airbnb positioned itself as the alternative to hotels.

Now things are getting a bit more complicated.

The platform announced it is adding thousands of boutique and independent hotels in cities including Madrid, Paris and New York. That means travellers opening Airbnb may increasingly find hotel rooms sitting beside apartments and holiday rentals inside the same search results.

And in reality, many users probably will not care very much about the distinction anymore if the booking process feels easier.

Especially younger travellers.People are becoming less loyal to specific types of accommodation and more interested in whatever feels practical, flexible and simple to organise.

That shift is part of why Airbnb appears to be changing strategy so aggressively now.

The company also knows business travellers remain a huge market. Traditional hotels still dominate that space because many people prefer consistency, reception desks and predictable services when travelling for work.

Airbnb seems to be trying to capture some of those customers too while still keeping the more relaxed aesthetic that made the platform popular originally.

Whether hotels like it or not, the lines separating travel apps, accommodation platforms and online travel agencies are becoming increasingly blurred.

Artificial intelligence is quietly becoming part of the experience too

Like almost every major platform right now, Airbnb is also pushing further into artificial intelligence.

But compared with some companies making vague promises about “AI powered futures”, Airbnb’s approach feels more practical.

The platform says it is now using AI systems to summarise over a billion reviews into shorter overviews designed to help people make decisions faster.

Which, honestly, many travellers will probably appreciate.Reading Airbnb reviews can sometimes feel endless, especially when you are trying to work out whether “cosy” means charming or simply tiny.

The app is also adding collaborative trip planning tools so groups can organise itineraries together more easily. Maps, accommodation details, activities and travel times can all supposedly be shared inside the same space instead of disappearing across different group chats.

There is also a more social angle appearing.

Airbnb wants users to see recommendations connected to friends and contacts who already visited certain places or made previous bookings. The idea is clearly to make the platform feel less transactional and more personal.

At the same time, customer support is becoming increasingly automated through AI powered assistance available in multiple languages, with voice support expected later this year.

Some people will love that.Others will probably miss speaking to actual humans.

But either way, Airbnb is changing very quickly and the company seems convinced that travellers want fewer separate apps and more all in one systems.

Whether that eventually makes travelling simpler or simply turns Airbnb into another giant tech ecosystem remains to be seen.

For now though, one thing is becoming obvious.The company that once mainly helped people rent holiday apartments is trying to become something much bigger.

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