Beyoncé and Jay Z caused major chaos two years back with an anniversary vacation down to Cuba. Faultfinders (okay, haters) complained that the pop power couple’s trip was illegal, a violation of the longstanding U.S. embargo against the Caribbean island. Well, that was 2013. As of January ’15, President Obama widely expanded the categories of authorized travel to the Communist island nation, to the point of allowing organized American tours for educational activities. Thawing relations between Cuba and the United States have already increased tourist activity 36 percent, and Black Americans beyond the MTV set are starting to do our fair share of indulging.

Up in the Air Life (the “upscale travel company dedicated to social adventures” founded by world traveler Claire Soares) boasts organized international jaunts for African-American vacationers to exotic locales like Mexico, Colombia, Greece, Croatia and Thailand. This year Soares targeted Cuba, coordinating a recent cultural tour of Havana for almost a dozen wanderlusting vacationers. Disembarking in Miami, the troupe spoke stateside with about Afro-Cuban entrepreneurialism, superior Cuban healthcare, and the effect of tourism on the struggling Cuban economy.

“Cubans are part of the same [African] diaspora, they were just dropped off before we were,” said Brandie Cobb, a Hampton-grad educator who’d just returned with the group. “They embrace us. It’s like, ‘you’re still our people.’ They’re just happy to see us. We went to the beach one day, and it was just like, ‘hey, you want some rum?’ We didn’t find really good rum until beach day,” she recalls with a laugh.

A capsule history of Cuba seems appropriate at this point, given the mandatory educational nature of American travel to the island. America set up a trade embargo against the nation in 1960, as a reprimand against former president Fidel Castro’s alliance with the Soviet Union and human rights violations connected to the country’s Communist control. Cuba’s free socialized healthcare predated Obamacare by nearly a half-century, and their medical system (highlighted in the 2007 documentary, Sicko) in many ways outstrips America’s.

“They could care less about a cellphone, the Internet, the latest fashions, a CD—because they played their own music and it was jamming,” said assistant principal Jevon Davis, who’d visited locals up in the Cuban mountains of Las Terrazas. “It was a brother-to-brother, sister-to-sister type of vibe, no matter where we were—whether it was a restaurant, a cultural center.”

On August 14, the American embassy in Cuba was reopened. (Cuba reestablished its own embassy in Washington D.C. the same day.) The U.S. government officially removed the island from a state-sponsored terrorism list back in May, and all signs point to the longstanding embargo being lifted in the foreseeable future. Marketing director Stacey Simmons voiced a shared sentiment among the Up in the Air Life travelers, namely the desire to visit before a lifted embargo changes Cuban culture with a heavy influx of American travel and trade.

“I think things will definitely change,” says Simmons. “One of the reasons why I went there now is to see it in its purest form. You’re definitely gonna see an increase in tourism, which I think is good for the country in terms of helping them improve their economy and infrastructure. But you’ll also lose a bit of that essence of what Cuba is.”

The Black August Hip-Hop Project was once known for facilitating cultural exchange between Cuban and American youth in the form of political education workshops and concerts. (Talib Kweli, Common, dead prez and Yasiin Bey are among the MCs who performed in Cuba on its behalf in the past.) Music may hold the key to future opportunities in Afro-Cuban entrepreneurialism should Cuba go the route of, say, Jamaica, and link its future tourism to music festivals akin to the annual Reggae Sumfest—bolstering the Cuban economy by embracing the local reggaetón and salsa styles on the island. “Just how Jamaica infuses Caribbean music with modern-day American music, they can infuse reggaetón with American music [for a music fest featuring] Rihanna or Pitbull or something like that,” suggests e-commerce manager Stephanie Richardson.

“There’s plenty of investment opportunities, especially for African Americans, because they would love to do business with us specifically,” says Jason Ridgel, president of Jusco Medical. “They feel closer to us, that there’s actually not a lot of difference [between us] at all.” In late May 2016, Up in the Air Life has another sojourn to Cuba planned for travelers to delve into the music, art, food, dance and cultural life of the island. Clearly now is the time to see the isle in all its time-bubble splendor, before the effects—positive and not-so-positive—of possible embargo lift take hold.—Miles Marshall Lewis

Miles Marshall Lewis is the Arts & Culture Editor of He’s also the Harlem-based author of Scars of the Soul Are Why Kids Wear Bandages When They Don’t Have BruisesThere’s a Riot Goin’ On and Irrésistible. Follow MML on Twitter and Instagram @furthermucker.