History of People-to-People Travel

Legal travel to Cuba was long a dream of American travelers, who were prohibited from visiting the island since travel restrictions were impossed in 1963. Policy changes in 1999 opened the door to legal travel to Cuba for Americans through people-to-people exchange programs, with the goal of enhancing cross-cultural relations between Americans and Cubans.

In 2000, Insight Cuba received its specific license from the U.S. Treasury Department’s Office of Foreign Assets Control, and pioneered some of the first Americans to legally travel to Cuba through its people-to-people programs.

When new travel restrictions were enforced in 2003, banning virtually all Americans once again from visiting Cuba, we remained hopeful that travel to the island would eventually resume. On January 28, 2011, and after an eight year hiatus, people-to-people travel was restored, meaning any American could once again travel to Cuba legally with Insight Cuba.  

Insight Cuba guests were the first to return in 2011 on our Inaugural Trips– a feat that attracted an unprecedented whirlwind of press from CNN, NBC, Reuters, Associated Press, and more than 200 other media outlets.  For details, listen to an interview with Arthur Frommer and Insight Cuba’s President, Tom Popper, or watch Peter Greenberg’s televised report on his trip with Insight Cuba.

Since our humble beginnings, we’ve sent over 6,000 travelers to Cuba, and currently offer six unique itineraries with over 100 regularly scheduled departures throughout the year. We’ve remained steadfast in our commitment to creating unique access to people and places the average tourist rarely sees. 

  • 1999

    Forty years after the Cuban Revolution, the Clinton administration announces measures to increase people-to-people exchanges between Americans and Cubans. Insight Cuba, a division of Cross-Cultural Solutions, sends in its first license application to the U.S. Treasury watnting to help Americans travel to Cuba legally and to build close relationships with the Cuban people.

  • 2000

    Insight Cuba is granted a two-year specific license from the U.S. Treasury Department's Office of Foreign Assets Control, authorizing legal, licensed people-to-people travel to Cuba. Thanks to its established ties to the Cuban people, Insight Cuba is among the first organizations to take Americans on people-to-people travel exchanges.

  • 2001

    Inspired by Cuba’s infectious rhythm and vibrant art scene, Insight Cuba launches a themed Cuban Music program, offering participants the chance to immerse themselves in Cuban music, dance, art and the people behind it all.

  • 2002

    Insight Cuba is issued a second, license authorizing legal, licensed people-to-people travel to Cuba. Shortly after, a partnership between JazzTimes magazine and Insight Cuba brings hundreds of Americans to the Havana International Jazz Festival. The pulsating, Latin experience draws big names in global jazz. Past performers include Dizzy Gillespie, Charlie Haden, Max Roach and Chucho Valdés.

  • 2003

    Insight Cuba is issued a third license authorizing, licensed people-to-people travel to Cuba. By year's end, Insight Cuba is featured in over 120 nationwide news outlets, including New York Times, Los Angeles Times and Newsweek. With established on-island ties and carefully fostered relationships, the organization sent over 3,000 Americans to Cuba since travel restrictions were lifted in 1999.

    Under the Bush administration, the regulations governing travel to Cuba are tightened, and all people-to-people educational travel programs are suspended. The last groups of Americans traveling under the license are Insight Cuba participants. They return home at the end of December 2003.

  • 2004

    Insight Cuba receives the Hospitality, Sales and Marketing Association International (HSMAI) Adrian Award for its efforts in the travel and hospitality industry. Considered the benchmark for the industry, this is the most prestigious travel marketing competition globally.

  • 2004-2010

    Insight Cuba continues to strengthen partnerships and friendships in Cuba while travel programs are suspended by the Office of Foreign Assets Control. Our hope remains steadfast that travel will soon resume.

  • 2010

    In August, Insight Cuba receives word that the loosening of travel regulations to Cuba is pending. We immediately begin preparing to relaunch Insight Cuba, in anticipation of resuming people-to-people travel.

  • 2011

    On January 28, people-to-people educational travel to Cuba is restored by President Obama (press statement). Insight Cuba submits its license application that very same day. On June 28 we are granted our fourth license authorizing, licensed people-to-people travel to Cuba. On August 11 we are the first organization in almost eight years to send Americans to Cuba legally under the new people-to-people regulations.

  • 2012

    In April, Insight Cuba sends its 6,000th American to Cuba legally.

    On September 28th Insight Cuba receives its 5th people-to-people license to legally send Americans to Cuba. 

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