Nothing signaled the rapprochement between Cuba and the United States quite like Beyoncé and Jay-Z’s visit to Havana in April, 2013. President Obama’s partial lifting of the travel ban finally allowed regular Americans to engage in “people-to-people travel” to Cuba. Under this category, anybody could join an organized educational trip and visit the island. In 2015 alone, 161,000 Americans traveled there, not including Cuban Americans. That number almost doubled in 2016.
General tourism remains off-limits to U.S. citizens, but 12 other categories of travel are now permitted (including professional research, journalism, religious activities, and people-to-people exchanges), opening the doors for Americans to visit Cuba. One sector that has greatly expanded under these rules is VIP travel.
The availability of luxury accommodations, particularly the proliferation of exclusive private restaurants and bars, have made Havana more palatable to VIPs. José Pineda, CEO of Miami-based Anthropologie Journeys, classifies his VIP clients into five groups: government officials, corporate and business executives, celebrities, high rollers, and affluent travelers.
“It’s really a matter of style,” says Pineda. “For example, one of the trips we did recently was for the families of two Hollywood producers, a group of ten people. They are affluent and have money and like to travel nicely. Paying $7,000 per person, they like to have the best that they can get in Cuba.
“A high roller would have as much or more money, but the kind of things requested in Cuba are a little more outrageous,” added Pineda. “We recently brought a group of single businessmen from LA, and they wanted to have very private parties, with Belvedere Vodka every day, which is something you have to bring into Cuba for them… The Hollywood families were content with what they had in Cuba.”
Academic Arrangements Abroad, a New York-based agency that has taken more than 10,000 travelers to Cuba over the last 20 years—including Beyoncé and Jay-Z—has also seen “a dramatic increase in demand for VIP travel to Cuba,” according to its president, Jim Friedlander. Over the last couple of years, they have sponsored and organized a slew of people-to-people trips for the boards of prestigious New York museums, Fortune 500 CEOs, judges, members of Congress, assorted billionaires and, yes, celebrities.
While most such VIP visits to Cuba are handled with discretion, the trip for Beyoncé and Jay-Z marked a departure from previous celebrity trips by its unprecedented degree of ostentatiousness and publicity. Their every move, smile and word was immediately tweeted and blogged, while media organizations––from Cuban state outlets to CNN––breathlessly competed for coverage. Images of the famous couple in Old Havana surrounded by fan mobs circled the globe. The $700-per-night boutique hotel where they stayed, the Saratoga, subsequently became a favorite of America’ s rich and famous, including Madonna and Jerry Springer.
Thanks to these celebrities, ordinary Americans now understand that Havana is no longer a Lonely Planet-type, off-the-beaten-path destination for exotica seekers. Rather, it has revealed itself as a vibrant metropolis with luxury hotels, glamorous paladares (private restaurants) and hipster nightclubs. A room at the Saratoga must now be reserved well in advance, as are tables at top eateries such as La Guarida and San Cristóbal, where the celebrity duo—and later President Obama—famously dined.
To critics, Beyoncé and Jay-Z’s trip looked more like leisure tourism than an educational exchange, prompting Cuban American lawmakers to demand an investigation. “Publicity attracts OFAC,” said Jim Friedlander, referring to the Treasury Department’s Office of Foreign Assets Control, which enforces the embargo. Friedlander’s company sponsored the trip, which was ultimately deemed in full compliance of the law. Most VIP travelers lucky enough to evade media recognition request non-disclosure agreements from the service-providing agencies.
Any U.S. organization that provides travel services to Cuba must navigate an intricate set of requirements. First, it must obtain an OFAC license to conduct business with the island. Next, it must be in good standing with the Cuban government in order to partner with one of three Cuban state travel agencies, most commonly Habanatur. When groups consist of more than six to eight unrelated people, the Cuban agency becomes the intermediary provider for local transportation, interpreters, guides, and other arrangements. The U.S. travel agency involved nonetheless keeps employees on the ground, to guarantee seamless service and quickly address any problems; when the groups are smaller, their people are the exclusive handlers.
VIP travelers typically arrive in Cuba via private jet or yacht, either their own or chartered. A designated terminal for private aircraft at Havana’s José Martí International Airport ushers visitors into the country with minimal customs and passport control hassle. Yachts, in turn, have the advantage of offering dependable accommodations and onboard dining, guaranteeing a high level of service even when sailing far from urban centers and tourist resorts.
VIP people-to-people trips usually involve complex arrangements, including meetings with high-ranking officials, famous artists and intellectuals, advanced reservations to restaurants, special private performances, and even excursions by helicopter.
“Our trips are distinguished by deep personal relationships, customized itineraries, and access that most people do not have,” says Friedlander. “They can cost $1,000 to $2,000 a day, but it can go higher if you want helicopters, yachts, and private jets. We have done $100,000-a-week trips.”
Ultimately, these VIP travelers––whether theyr’e objects of media spectacle or they travel under the radar––end up as ambassadors for the normalization of U.S.-Cuban relations. “The people we bring are opinion leaders, and they have all have come away with a deeper understanding and appreciation of better [Cuban] relations with the U.S.”
Upon his return in May 2016, talk-show star Jerry Springer proclaimed his trip to be “a life-changing experience.” His five-day jaunt entailed meeting and jamming with folk musicians and eating “at the samepaladar that Obama went to”—Paladar San Cristóbal.
“We define freedom as our government not telling us what to do. They define freedom as another country not telling them what to do,” said Springer, urging his viewers to travel to Cuba “before it looks like Miami Beach South.”